Club Shay Shay - Sheryl Underwood Part 1

Summary

Podcast Summary: Club Shay Shay - Sheryl Underwood Part 1

Podcast Information:

• Title: Club Shay Shay
• Host/Author: iHeartPodcasts, The Volume, and Shay Shay Media
• Description: NFL legend Shannon Sharpe—3x Super Bowl champion and member of the Pro Football Hall of Fame—sits down with the biggest athletes, celebrities, and influencers to discuss their accomplishments, challenges, and everything in-between.
• Episode: Club Shay Shay - Sheryl Underwood Part 1
• Release Date: January 22, 2025

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Introduction to Sheryl Underwood

In this episode of Club Shay Shay, host Shannon Sharpe welcomes Sheryl Underwood, a celebrated comedian and television personality with over 35 years in the entertainment industry. Underwood is recognized for breaking barriers as a comedian, winning Daytime Emmys and NAACP Image Awards, and being a member of the Arkansas Black Hall of Fame.

Notable Quote:

"I am a doctor four times, even though it's bestowed. But I wanted to be able to sit across from my lawyer and understand the contracts I sign."
— Sheryl Underwood [12:31]

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Early Career and Comedy Beginnings

Sheryl Underwood shares her journey into comedy, detailing her initial foray into lingerie modeling in Chicago to support her education. Realizing her lack of talent in modeling, she pivoted to comedy, inspired by family members known for their humor.

Notable Quote:

"That's when I knew I was funny. Because God let me know what I was not supposed to be doing."
— Sheryl Underwood [11:18]

Underwood recounts her first experiences performing stand-up comedy, highlighting her determination to excel despite challenges and societal expectations.

---

Balancing Education and Career

Underwood emphasizes the importance of education in her career, earning multiple degrees to empower herself in the business aspects of entertainment. Her educational background enabled her to navigate contracts, understand financial matters, and effectively run her enterprises.

Notable Quote:

"I wanted to be able to sit across from my lawyer and understand the contracts I sign. I want to be able to run a corporation. We are corporations."
— Sheryl Underwood [12:31]

---

Television Experiences and Mentorship

Discussing her television career, Underwood highlights her appearances on shows like Def Comedy Jam and Showtime at the Apollo. She shares memorable interactions with fellow comedians, including Damon Wayans and Bernie Mac, who played pivotal roles in her professional growth.

Notable Quote:

"Bernie was the kind of guy that if he felt he could help you get that joke tighter or advance your career, he was that guy."
— Sheryl Underwood [45:26]

Underwood also touches upon her experiences on The Talk, sharing insights into the dynamics of daytime television and her aspirations to produce content that elevates female comedians.

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Vision for Content Production and Supporting Female Comedians

A significant portion of the conversation revolves around Underwood's vision to produce inclusive content and support the next generation of female comedians. She advocates for collaborative efforts within the comedic community to create opportunities and break down barriers for women in entertainment.

Notable Quote:

"We have to come together. There's enough money out there for all of us."
— Sheryl Underwood [84:16]

Underwood expresses her desire to produce movies, sitcoms, and other media that showcase the talent of female comedians, emphasizing the need for unity and mutual support.

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Personal Anecdotes and Life Lessons

Underwood shares various personal stories, including her struggles with auditions, handling criticism, and maintaining professionalism in the face of adversity. She reflects on the importance of resilience, adaptability, and staying true to one's values and comedic style.

Notable Quote:

"When you get the opportunity, you gotta be ready for the opportunity."
— Sheryl Underwood [40:48]

---

Perspectives on Relationships and Gender Roles

The conversation delves into Underwood's views on relationships, gender roles, and societal expectations. She discusses her experiences with dating, emphasizing the importance of mutual support and understanding within partnerships.

Notable Quote:

"I want the language to be relaxed. I wanna be able to ask, 'What was you thinking?' That's what I wanna ask."
— Sheryl Underwood [20:03]

Underwood advocates for balanced relationships where both partners contribute and support each other's ambitions, challenging traditional gender norms.

---

Conclusion and Future Aspirations

As the episode progresses, Underwood outlines her future aspirations, including expanding her content production ventures and continuing to champion the cause of female comedians. She emphasizes the ongoing journey of growth and the importance of leveraging platforms like Club Shay Shay to foster meaningful conversations and collaborations.

Notable Quote:

"We need to change that narrative. And I know you can, because you took a little Club Shay Shay and made it big."
— Sheryl Underwood [81:20]

The episode concludes with Shannon Sharpe teasing the continuation of Underwood's story in Part 2, encouraging listeners to stay tuned for further insights and discussions.

---

Key Themes:

• Career Transformation: From modeling to comedy
• Education and Empowerment: Leveraging education for business acumen
• Mentorship and Collaboration: Relationships with influential comedians
• Supporting Female Talent: Creating opportunities and inclusive content
• Personal Growth: Resilience and adaptability in the entertainment industry
• Balanced Relationships: Challenging and redefining gender roles

Notable Quotes with Timestamps:

• "I am a doctor four times, even though it's bestowed..." — Underwood [12:31]
• "Bernie was the kind of guy that if he felt he could help you..." — Underwood [45:26]
• "We have to come together. There's enough money out there for all of us." — Underwood [84:16]
• "When you get the opportunity, you gotta be ready for the opportunity." — Underwood [40:48]

This episode provides a comprehensive look into Sheryl Underwood's multifaceted career, her dedication to empowering women in comedy, and her unwavering commitment to personal and professional growth.

Transcript

[Shannon Sharp]

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[Cheryl Underwood]

Check.

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[Shannon Sharp]

So what's the dating scene like for Cheryl Underwood?

[Cheryl Underwood]

Okay, go ahead. Let's play the role. Action. Ask me out. Ask me out.

[Shannon Sharp]

My name is Shannon Sharp. How you doing?

[Cheryl Underwood]

I know you. Come on, let's go. All I Gotta do is take these muscle relaxers. I don't know why you even think you need tell me your name. I'm already taking my clothes off before I even got in the car. Why is this bitch naked on the curb? All my life been grinding all my life Sacrifice, hustle, paid the price Want a slice, got to roll a dice, that's why all my life I been grinding all my life Look. All my life been grinding all my life Sacrifice, hustle, paid the price Wanna slice, got to roll a dice that's why all my life I've been grinding all my life.

[Shannon Sharp]

Hello. Welcome to another episode of Club Shay Shay. I am your host, Shannon Sharp. I'm also the proprietor of Club Shaysay. Today we're at the Beautiful 8 Lounge at Resorts World Las Vegas. Stopping by for conversation on the drink today is one of America's most loved television personalities. She's broken barriers as a comedian for over 35 years. Daytime Emmy and NAACP Image Award winning television host. A talented actress, a hilarious performer and entertainer, sought after public speaker, multi talented media personality, an acclaimed executive producer, prolific writer, savvy businesswoman and successful entrepreneur, multifaceted philanthropist, a member of the Arkansas Black hall of Fame, a proud diamond life, member of Zeta Phi Beta sorority, one of the most entertaining acts around. A legendary comedian, the one, the only, Cheryl Underwood.

[Cheryl Underwood]

Then why the we ain't married then? You done gave all my damn credits. Now here's what you thought was gonna happen on your show. This is Club Shay Shay. It's Club Cheryl Cheryl now.

[Shannon Sharp]

Okay, go ahead.

[Cheryl Underwood]

We sat in the car in Denver.

[Shannon Sharp]

Yes.

[Cheryl Underwood]

I'm gonna tell the story, right. Cause when you came on the talk, you walking out with the flower looking all dashing and I was like, this is the same dude I was trying to pull in the 1993 Denver. Yeah, man.

[Shannon Sharp]

Yes.

[Cheryl Underwood]

Okay, ladies, you wanna tell.

[Shannon Sharp]

This is how it happened.

[Cheryl Underwood]

You wanna tell? You tell it.

[Shannon Sharp]

Okay. I saw her on Def Comedy on comic view in 1992.

[Cheryl Underwood]

Uh huh.

[Shannon Sharp]

And she was performing in Denver. Me and a couple of my teammates went to the. They were like, man, Cheryl Underwood performing. I like, man, she funny as ish. I said, let's go check out. So we go check out.

[Cheryl Underwood]

Yeah.

[Shannon Sharp]

And so at the end of the show, it's late. I mean, I think I saw the late show. And I say, man, you know, I want to go back here and meet. It's like, do she know you? I was like, nah, she don't know me. But she's like, okay. So they knock on the door, you come In. I introduce myself. Hey, I'm Shannon Sharp. She's like, and I know who you are.

[Cheryl Underwood]

That's right. Show me you ain't got to do.

[Shannon Sharp]

All that for him.

[Cheryl Underwood]

Now that he's proprietor of Club Shay Shay. He don't know how to say no more. But that's all right. When we was in the car. You sure know how to say it. Yeah. Cause we was in the car.

[Shannon Sharp]

We was in the car.

[Cheryl Underwood]

You ain't telling the story right.

[Shannon Sharp]

Hold on. It was late and she's like, okay, I'm going back. I said, you know what? I'll give you a ride to your hotel. I. I thought I was just gonna give her a ride to the hotel. We talk on the way to the hotel, she get out. She like, oh, no, Ian, you finna talk to me.

[Cheryl Underwood]

I was like, listen, he ain't telling it right. Let me tell you what really happened. So you walked up to me, big sexy ass black nigga. Matter of fact, what you need to do? Put some lotion on your ashy ass hand right here.

[Shannon Sharp]

I did.

[Cheryl Underwood]

Yeah. Your knuckles looking like Wesley Snipes. Get it together, boy. You too rich to be looking ashy. Two dark skinned negroes wearing glasses don't need to be ashy on this show.

[Shannon Sharp]

I'm ashy, lady. I guess I'm done here.

[Cheryl Underwood]

Yes, you are. Yeah, you ash. Listen, you better know it. So here's what happened.

[Shannon Sharp]

Okay? What happened?

[Cheryl Underwood]

So I'm looking at you as your sexy butt, and it is quite late. Get it right. So then you said, well, what would you like to do after this?

[Shannon Sharp]

Yes.

[Cheryl Underwood]

So I thought to myself, you know, what would any other woman want to do? I said, I would like to go on the carriage ride. You said, I will take you. I said, hold on, let me finish selling these CDs, these tapes, these cassette tapes, these posters. Remember that?

[Shannon Sharp]

Yes.

[Cheryl Underwood]

And so you are walking up the stairs and I'm still trying to get my money. And some women in the. You go, come on, if you're gonna go. And I go, who the you talking to, right? Cause we just met, we not in a relationship. No, you talking to me like we've been together for years. Cause you go, come on, if you wanna go.

[Shannon Sharp]

Cause if you go, I'm going, I gotta go to work in the morning. I ain't got all night, okay?

[Cheryl Underwood]

And so the women go, you know he's calling you. He said. I said, I don't give a. I've been Cheryl Underwood long before. So then we get in the car, can't find the carriage rod. So we talking. And we talk all day. All day.

[Shannon Sharp]

We talked for about two hours.

[Cheryl Underwood]

Sure did. And we became good friends.

[Shannon Sharp]

We exchanged numbers until this day.

[Cheryl Underwood]

That's right.

[Shannon Sharp]

Every time. If I'm somewhere and she's there, we're gonna find a way to connect.

[Cheryl Underwood]

Absolutely.

[Shannon Sharp]

She's been this Cheryl.

[Cheryl Underwood]

Yes.

[Shannon Sharp]

Since I met her in 1993.

[Cheryl Underwood]

Yes. And I'm very proud of you and what you have achieved. The question I have for you is what the is in the cognac to make these dudes come on this show and bitch up like they up talking about each other. When did men start gossiping? Shannon, what is in this that make people tell stories? First of all, let's click on it. Cause two country negroes drinking brown liquor. Isn't America great?

[Shannon Sharp]

Unbelievable.

[Cheryl Underwood]

Unbelievable. Well, see, I like to sip mine. You like, choke yours down.

[Shannon Sharp]

Now you sipped it.

[Cheryl Underwood]

I was trying to Bill Cosby you one night, but you wouldn't go for it. I said, go and drink. Go and drink it. Go and drink. Go drink it. Go drink it. And we never had the Instagram accidentally press the button.

[Shannon Sharp]

There you go.

[Cheryl Underwood]

No. Cause I'm too savvy for that. Listen, ladies, every red light ain't no smoke detector. You gotta know about dudes. You gotta look under the bed. You gotta see if there's people in the closet. You know what I'm saying? I came to talk to you. Now there's three more teammates in the closet waiting on me. Okay, listen, what are we supposed to be talking about? Let me move my lotion. Cause you look like you need some more.

[Shannon Sharp]

No, I'm good. I'm good. I'm good. Dang.

[Cheryl Underwood]

What is in cheat? Let me ask you a yes. What is in this that makes. I'm not against dudes coming on here.

[Shannon Sharp]

Right.

[Cheryl Underwood]

But what is making them tell these stories that they telling?

[Shannon Sharp]

I think the fact is that they want to get this off their chest. They've been holding this for a long time, and they wanted a safe space that they feel they could share this.

[Cheryl Underwood]

What I love is no women come on here beefing like these dudes beef. Which I think is very entertaining. But I have said in my comedy show, the Mix and Mingle Tour 2025, okay, if we could get as people that watched the episodes of all the great confessions to vote, we would be in a different political space.

[Shannon Sharp]

You would have.

[Cheryl Underwood]

So I need you to use your platform to encourage good things. Now, I notice that you kind of throw it out there and then let them get Full of this liquor and then start talking and popping off in the mouth.

[Shannon Sharp]

No, no, no. We toast to begin.

[Cheryl Underwood]

Cheryl. Yeah, we toasted.

[Shannon Sharp]

Okay, we toast and then that's it. Now, if they wanna pour a little bit more. I don't pour em anymore. That's right, yeah. If they wanna talk, I let em talk.

[Cheryl Underwood]

And you let em just talk the way they talk? Yes, but don't you think it's. Well for me? I'm glad there's no females doing this. I'm glad we don't come on here.

[Shannon Sharp]

I really ain't had a whole lot. I'm trying to get more.

[Cheryl Underwood]

Who you trying to get?

[Shannon Sharp]

Shout em out. I'm trying to get some more. Adele Gibbons.

[Cheryl Underwood]

I think it'd be great. I think it'd be great.

[Shannon Sharp]

Adele Gibbons.

[Cheryl Underwood]

Me and Adele got long stories. Me and Samor long stories. You heard about when I accidentally dialed into the country.

[Shannon Sharp]

We gonna get to that?

[Cheryl Underwood]

We gonn.

[Shannon Sharp]

Yeah, yeah. You're trying to. Hey, let me do my job.

[Cheryl Underwood]

Do your job.

[Shannon Sharp]

Okay, let's start off with this.

[Cheryl Underwood]

What?

[Shannon Sharp]

Is it true that you started off as a lingerie model in Chicago?

[Cheryl Underwood]

Yes, that's what we were calling it. It was lingerie modeling. It was a tavern off Stony Island.

[Shannon Sharp]

Okay.

[Cheryl Underwood]

I answered an ad. I was trying to pay my way through school, okay? My dad was giving me a place to stay and helping me as much as he could, and I needed to make money. And so I answered an ad. And you know I can't walk in heels. Everybody know that, right? So what happens is you put on the lingerie, you model it, and then the guys, if they like it, they'll buy tip you to take it off. Oh, that's what it you stripping.

[Shannon Sharp]

The hell talk about you did your lingerie.

[Cheryl Underwood]

What the. I just got off cbs. Can you calm the. I'm trying to get back on daytime tv. What are you doing? No, I was not stripping. I was not surfboarding. I was not. I don't have that kind of skill, that strength, you know, I don't have.

[Shannon Sharp]

That, what they call it now. Okay, five for the 20 for the top and 20 for the bottom. Take that off. Okay. Boom. So they were paying for you to take it off?

[Cheryl Underwood]

No, they was paying for me to keep it on because I was horrible. That's what happened. I was horrible. That's when I knew I was funny. Because God let you know what you not supposed to be doing.

[Shannon Sharp]

Okay?

[Cheryl Underwood]

Okay, So I think I'm over here doing it. Doing it, doing it, doing it, doing it. Well, they Was like, no, go home, go home. What you need money for school? Them hood dudes was like, here, take this money. Go home, go to school. Cause this you cannot do. And I'm not good at it. That's why if you have sex with me, it better be lights off. And what did Eddie Murphy say in the movie? Can you make it darker? Because I do not show you certain things. People think because of the type of comedy I do, it's very sexual and profane, that I'm just throwing it out there.

[Shannon Sharp]

That ain't true.

[Cheryl Underwood]

I'm not, I'm not. I'm really kind of reserved, you know. But I was doing that to pay my way through school.

[Shannon Sharp]

So that's true. Cause I hear that a lot of times they're like, I'm only doing this to pay my way through school. Once I get through school, I'm gonna be done with this.

[Cheryl Underwood]

Well, I only had a few days to do it. Cause I was garbage. And that's what happened. And that's why I had to get into comedy. And you know, when you make a hood dude laugh. Hood. Yeah, you funny.

[Shannon Sharp]

You done something.

[Cheryl Underwood]

You funny, right? So that's when I knew I was funny.

[Shannon Sharp]

So check this out. You got an associate's degree from Fresno City College, a bachelor's degree from the University of Illinois at Chicago, a master's degree from Governor State University in Chicago, and an attorney assistant certificate in ucla. What the hell you need all them degrees for, Cheryl?

[Cheryl Underwood]

I thought I was gonna go to law school while I was working on my comedy career. And I have four honorary doctorates, three of them from HBCUs, Voorhees College, Benedict College, and South Carolina State. And one from my own alma mater, University of Illinois Chicago. So I am a doctor four times, even though it's bestowed. But I wanted to be able to sit across from my lawyer and be able to understand the contracts I to sit across from my accountant, be able to understand the numbers. I want to be able to run a corporation. We are corporations.

[Shannon Sharp]

Correct.

[Cheryl Underwood]

I did not want someone to be able to over intellectualize my life when I didn't understand what was going on. So I felt if I got an education, I could stand toe to toe with anybody and I can talk to anybody. I've been to the White House, you know, when President Obama came in, the only reason I was cautious about going because my father was not alive to see a black man become president of the United States. And that kind of made me feel melancholy. But when you talking about where we come from who we are to be able to do what we're doing. There is some sophistication to that. Most comics, very, very smart athletes, very, very smart. But people don't want to portray us as that. We created all knowledge, art, law, medicine. Go back to the motherland and you will see what we created. Navigation we were in countries. Go back and look at everybody's statues and you will show that we were there. It's a statue of somebody look just like you in every country out there. Every country your was in Game of Thrones before they even moved to.

[Shannon Sharp]

So you wanted to do all this?

[Cheryl Underwood]

Yes.

[Shannon Sharp]

But comedy got you sidetracked?

[Cheryl Underwood]

No, comedy is where I made my money. Comedy is where I found I could make money. I mean, I had jobs. I was a waitress. You know, I did my jobs on campus and things like that. But where I found that I was most prolific was comedy. And I remember calling my father and telling her I was going to do a show called Def Comedy Jam, okay? And my father, you know, very spiritual family, you know, and I said, daddy, I'm gonna do this show on hbo. He said, what is it? It's called Def Comedy Jam. What you gonna be doing? I said, I'm gonna do comedy. You? Yeah. I was like, yes, sir. Yes, sir. I'm Drew Comedy. The only thing he asked me was, was I good at it? And I said, I'm one of the best at adult comedy. I'm good at it. He said, because he called me his son, because I'm his firstborn, okay? He said, son, as long as you are the best at it, I will support it. And I'm going to pray that God gives you time the way he gave. You know, we country people talk. Eddie Murphy, you know what I'm saying? And Richard Price. So he prayed for that. But he never came to see me live because after he got saved, gave his life to Christ, he said he told God he would not go into a nightclub, a tavern, a bar or anything. So he never saw me live, but he would watch me on tv. And he got a kick out of the profane because he said, people would love to see you with your little glasses on with a Bible in your hand, but that's not what you're portraying.

[Shannon Sharp]

That's not what you're called.

[Cheryl Underwood]

That's not what I'm portraying. But I do sprinkle God in the show because I believe God knew me before I knew myself. So for me, comedy was the thing that paid my bills. Comedy was the thing that I loved and has Loved me back unconditionally, and I believe I'm good at what I do. And I never planned to be a female comic. I wanted to be a great comic. And when Chris Rock says on the 25th anniversary of DEF County Jam, the two people he didn't want to follow. Bernie Mac and me. That's a badge of honor.

[Shannon Sharp]

Wow.

[Cheryl Underwood]

Mmm.

[Shannon Sharp]

Sheryl, when did you know you were funny? Were you funny as a kid?

[Cheryl Underwood]

No. I'm doing an impersonation of my father and my brother, my oldest brother. All my family members are funny. My Uncle William, Uncle Junior, Uncle Bill, all my uncles, Uncle Cliff. All of them are funny on both sides of my family. Mother, father, you know, everybody's funny. So I would just sit in the kitchen, and I was trying to figure out. I started as a singer, you know, singing a church choir, you know, but when you black and you sing, you got to sign. You can't just.

[Shannon Sharp]

Yeah.

[Cheryl Underwood]

You can't just play around with it. So I had to really find something I could do. I started as a dancer. That's how I got into what I call sexual interpretive dance.

[Shannon Sharp]

Yeah, but you weren't good at that.

[Cheryl Underwood]

I wasn't good at that. I was gonna be Lola Falana, you know, Paula Kelly, you know, how old I am. So I thought I was gonna be that. But then when I couldn't cut into that, I said, I gotta find a way. Because I knew I wanted to be in the entertainment business, because I wanted to be in a business that would appreciate all of my talent as performer and producer. So once I got the comedy and found I could do it, and there was a certain type. It was political, sexual, and spiritual. That's what I do. And I found a way to do it well and then get dropped on a daytime. Daytime talk show.

[Shannon Sharp]

Yeah. Hello. You had all these jobs.

[Cheryl Underwood]

Mm.

[Shannon Sharp]

You interned for Oprah at lstv.

[Cheryl Underwood]

Wow. Y'all dug deep.

[Shannon Sharp]

Yeah.

[Cheryl Underwood]

Yeah.

[Shannon Sharp]

Did you have. Did you have interactions with Oprah?

[Cheryl Underwood]

Absolutely. Absolutely. And Oprah is a very smart and prolific person with a great sense of humor. But, see, I was living in Chicago.

[Shannon Sharp]

Okay.

[Cheryl Underwood]

So we would. I remember when Steadman was a model and he had a billboard across Cottage Grove, and he was playing basketball, I think, overseas. And, you know, they would bring all the. You know, go up to Trinity, you know, church. You know, we chur. We. 87th Street Church of Christ. They Trinity. You know, you can go to all church. I go to all churches because I want to enjoy the word of God preached by somebody that know the Lord. And with some great music and a good dinner after it's over and be able to buy soda. But for me, seeing Oprah Winfrey and then becoming a talk show host on my own, I think she opened the doors for us. But one of the things that I remember is when she came to Chicago in the 80s, it was the Bud Billiken Parade, and it was raining, and we were all looking at the TV going, we hope this sister makes it. And look at what God has done for her life.

[Shannon Sharp]

Did you. When you were interning for Oprah, did you have any idea she would become what she later become what she is today?

[Cheryl Underwood]

Yeah, you can see it. You can see it. And I believe in friendly competition, you know, for people to say, oh, she knocked off Donahue. No, what she did was elevate the game so it could go to a different level. And I would like to do the same. And since you over here giving people podcast jobs and all kind of jobs, okay, how can I be down? And I need my money in cash, ain't it? Cause you know, if we wasn't gonna kick it like we should've kicked it. I need my money in cash. You try to do a pod, I would. You gonna produce it?

[Shannon Sharp]

Yeah.

[Cheryl Underwood]

Okay, now listen to me. Don't be just. Cause we, you know. Where the camera at? I need to look at this.

[Shannon Sharp]

Your camera right here. You been in TV for 25 years now.

[Cheryl Underwood]

I need to tell the world. This is a commitment, brothers and sisters, something that he doesn't do well. So you've heard him say it.

[Shannon Sharp]

That's cj. CJ handles Club. Shay. Shay in the podcast, you would do one?

[Cheryl Underwood]

Yeah, I would.

[Shannon Sharp]

Yes, absolutely.

[Cheryl Underwood]

Okay. What would you suggest that I do? Cause I have an idea.

[Shannon Sharp]

Well, that's on you. Because if you do it authentically, if this is something that you really wanna do, as opposed to me telling you what I think you should do, it's gotta come from here.

[Cheryl Underwood]

I know what I wanna do. Okay, well, I wanna be everything I couldn't do in daytime. I wanna do it at nighttime.

[Shannon Sharp]

Okay.

[Cheryl Underwood]

I want the language to be relaxed. I wanna be able to ask. I wanna be able to. One question.

[Shannon Sharp]

What.

[Cheryl Underwood]

What the was you thinking? That's what I wanna ask. To me, that is the show. What the was you thinking? And I want to be small, cozy, with a little bit of audience. And whether you are social media phenomenon or a politician, I wanna ask Republicans, now that y'all won, you broke it, you bought it. What you gonna do? What you thinking? You know what I'M saying? I wanna ask Democrats. So when you lost, what you gonna do now? You know what I'm saying? I wanna be able to ask athletes questions. Like old boy with the girl, right? He love her. You know who I'm talking about?

[Shannon Sharp]

You talking about Jalen Green with Dre or Michelle?

[Cheryl Underwood]

No, the other girl.

[Shannon Sharp]

Travis.

[Cheryl Underwood]

Travis.

[Shannon Sharp]

Travis Horner. Yeah, okay.

[Cheryl Underwood]

He love her, don't he?

[Shannon Sharp]

Yeah.

[Cheryl Underwood]

Okay, but now he won't be able to sample the greatness of the buffet that God is about to lay in front of him, will he, if he stick with that one girl?

[Shannon Sharp]

He might. That's all he want. He might just. His palate might not.

[Cheryl Underwood]

That's all he want right now.

[Shannon Sharp]

His palate might not be. You know.

[Cheryl Underwood]

Listen to me. Okay, listen. Go ahead. My dad.

[Shannon Sharp]

This your camera?

[Cheryl Underwood]

Listen to me. I done went through two different conferences, different leagues. I done wore four, five super bowl rings. I done went defense, offense and defense.

[Shannon Sharp]

Stop diming people.

[Cheryl Underwood]

Listen, I'm not diming people out. You know, Wait. I lost somebody over a misunderstanding.

[Shannon Sharp]

What's the misunderstanding?

[Cheryl Underwood]

Okay, so I'm a name. Well, I don't know if I want a name name. Cause I don't know.

[Shannon Sharp]

You ain't gotta name no name. But what was the misunderstanding?

[Cheryl Underwood]

Okay, so I thought I was dating the quarterback of a football team, okay? And I was really happy then. I thought I was gonna put on an apron and live happily ever after while I still work in comedy. Things were going well. I taped Laugh a Palooza with Jamie Foxx. Jamie Foxx. Marcus King had a great set, great political set. Thought I was gonna bomb because everybody was doing a club set when Baby Bush was in office after September 11th. And I was doing some very sophisticated hood political material. Go get the tape and you'll see what I was doing. Get a standing ovation in the set. David Alan Grier comes around the corner. I can tell the story because he tells it, too. David Alegria comes around the corner. I think he's going to hug me, to congratulate me. He slobs me down, tickle them tonsils, all the way down into the esophagus in the epiglottis, all the way down in the intestines, all the way to where I was trying to find David Alan Grier that night. And then when the tape, when the show comes out, I get a phone call. I don't think this is going to work out. I said, what are you talking about? And you kiss some other men. Who did I kiss? Then he tells me, what is I didn't kiss him, he kissed me.

[Shannon Sharp]

Why didn't you tell him though and say, look, there's gonna be a situation that I did very well in my set. And a friend of mine, he came and he, you know, he gave me a kiss.

[Cheryl Underwood]

I didn't think Jamie and them was gonna leave it in the footage. I thought it was congratulations. I thought it would have been me. They left it in the footage so I didn't see it. I don't watch me after it's, you know, edited and everything. Because I'd be like, oh, they took out the joke about the frog in the diaper. You know, I don't do that. So when they left it in there and then what bothered me is you didn't ask me anything, you just told me. Why do strong athletic men get upset about the littlest thing? You win a damn super bowl, it's all over you. I'm not gonna be mad, but that.

[Shannon Sharp]

Don'T mean he tongued them down.

[Cheryl Underwood]

Yeah, but if you want to, you can. Matter of fact, I need four of you to tag in. Cause I'm not doing all this work. Tag in. Come on, get this. Can I say it? Come on, get this. Long stroke. Cause I'm not doing it. I'm gonna go outside and make sandwiches. Cause you look like you gonna be hungry after this. I'm over there massaging shoulders. You can handle this girl. I've been taking this pounding every night. You can do it. Come on in. If you and I was married.

[Shannon Sharp]

Yeah.

[Cheryl Underwood]

If let's say you and I was married and you wanted to, what would be the freakiest thing you would want to do? Cause I know you freaky.

[Shannon Sharp]

I ain't really that freaky. Shut up, public. I like the thought of being caught, but not being caught. So the probably of somebody walking by and actually seeing me.

[Cheryl Underwood]

Oh, you voyeuristic.

[Shannon Sharp]

Yeah.

[Cheryl Underwood]

You want somebody to see you?

[Shannon Sharp]

Yeah.

[Cheryl Underwood]

Okay. Would you wanna do a fivesome? You and four women?

[Shannon Sharp]

Nope.

[Cheryl Underwood]

Why?

[Shannon Sharp]

One on one.

[Cheryl Underwood]

One on. No wonder I dodged a bullet that night. Cause I wasn't takin all of that.

[Shannon Sharp]

No.

[Cheryl Underwood]

When you got out the car, I said guys. And then I said thank you, Jesus. And then when you was like, well I'm gonna go home and go to bed, I was like, woo. Cause I wasn't taking all that. Cause you know I'm short, you know, your big blocking out the moon. I was like, oh, thank you, thank you. I wasn't taking all of that. And for all you women that wanna have sex with that guy, Mm, mm, mm, mm, mm, mm, mm, mm. He ain't bringing nothing to show up.

[Shannon Sharp]

What's up, guys? It's your favorite unc here, Shannon Sharp. I want to let you guys in on something. I'm proud to be a Ro partner, and today we're talking confidence. Because confidence isn't just how you walk into the room. It's also about how you handle business once you're in the bedroom. You know what they say. If you stay ready, you don't have to get ready. That's where row Sparks come in. Row Sparks are the two in one prescription treatment designed to help you get stronger, harder, fuller erections that dissolve right under your tongue and hit the bloodstream fast, working in just about 15 minutes on average. That means more time for the good stuff and less time for waiting. And let me tell you, Sparks keeps you in the game for up to 36 hours. You're ready to go for round two, three, or even in the morning after. Plus, Sparks makes it easy. Everything is done 100% online. No awkward conversations in the doctor's office. If approved Sparks shipped straight to your door. If prescribed new sexual help, patients get $15 off sparks on reoccurring plans. To find out if the prescription Ro Sparks are right for you, connect with your provider at Roast Co Shay Shay. That's Ro Co shay shay. For $15 off your first order, compounded.

[Cheryl Underwood]

Drugs are permitted to be prescribed under federal law but are not FDA approved. For full safety information, visit Ro coinfo Jerry Springer.

[Shannon Sharp]

Were you on Jerry Springer?

[Cheryl Underwood]

Yes, I was.

[Shannon Sharp]

How the hell you get on Jerry Springer?

[Cheryl Underwood]

So I used to do jokes about my complexion, okay. Now people say, well, why do you talk about the way you look? Why do you talk about. Because self depreciation in comedy is a standard to talk about yourself. I really don't like to talk about people. Cause people get their feelings hurt.

[Shannon Sharp]

They do.

[Cheryl Underwood]

You know, they get the feelings hurt. But I will talk about people generally. But then at that time I was talking about being darker skin. You and I both had this same conversation.

[Shannon Sharp]

Yes.

[Cheryl Underwood]

We are pretty black. Am I right?

[Shannon Sharp]

Yeah.

[Cheryl Underwood]

Body look all one color. If you lay down on the table right now, you gonna disappear. Cause your body is all one color.

[Shannon Sharp]

Correct?

[Cheryl Underwood]

Right. So I was doing jokes like that. So then someone said, would you come on Jerry Springer? We're gonna talk about light skinned it versus dark skinned it. And me and my sister went on there. Cause my, you know, we all have that in our family.

[Shannon Sharp]

Yeah.

[Cheryl Underwood]

One of us is this, one of us is that. And it was a great experience and it taught me how to do tv. Cause I was hitting them jokes. I was hitting them jokes and that's how I got a reputation to be on tv. And if it wasn't for Jerry Springer appearance and the View, wow. If it wasn't for the View, I don't think I would have landed on the Talk because they may not have seen me or may have felt because my comedy is so adult that I couldn't do daytime tv.

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[Cheryl Underwood]

Okay ladies, when I said we came to play, didn't I mean it? This Disney cruise got me feeling like we can get massages at Sense's spa, have a meet and greet with Black Panther. Oh, I love him. And I can't wait to sunbathe on the private island. And the kids will be fine. Girl, they're good. Exactly. While they hang in the kids club with Mickey Mouse, we can do our thing and do it well all day. Disney Cruise Line is where we came to play.

[Shannon Sharp]

Hey guys, this is Matt Jones, Drew Franklin from the Fade this podcast. We got a great episode coming up.

[Cheryl Underwood]

Picks in all the sports.

[Shannon Sharp]

Football, basketball, we do them all. But there's a preview of this week's episode.

[Cheryl Underwood]

I've seen people in the gambling community kind of make jokes about fade this and we just goof off and don't even talk about the games. Bring your records and set them on this table right now. All you out there that are spend two hours talking about the games and will in the last seven years and night games they've come in and haven't scored 20 points and you get too detailed. Bring your records right here to fade this. We'll we'll talk about books and cooking and Kevin Costner and still make more money betting on sports than you will.

[Shannon Sharp]

And this episode was brought to you in partnership with DraftKings. To hear more, listen and subscribe to Fade this on iheartradio or wherever you.

[Cheryl Underwood]

Listen to podcasts with the best all.

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[Shannon Sharp]

Could get on stage? And you know what? I could. I can actually make a career. I can make a living doing this.

[Cheryl Underwood]

When I got paid for it. When you paid me for it.

[Shannon Sharp]

I can do it.

[Cheryl Underwood]

That's right. I can do it. And, you know, first you get a little bit of money. Get enough money to fill your gas tank up. And I remember working at Republic Insurance in North Hollywood in California, and I was an underwriter. So I would work my 8 to 5 job, keep my club clothes in the trunk of the car, go drive and do a gig and sometimes drive to three different cities in Southern California that night, and then come back to the job, sleep in my car and go to work. But that's what a college education did for me. But a street sensibility, that grind, that hustle, is what made me do it. I have to succeed. Even getting on Def Comedy Jam. I was trying to get on Def Comedy Jam and they heard about me, but I was performing under two names, my maiden name and my married name. So I think they thought it was two different people. So by the time my husband dies and I move to Los Angeles, I'm still trying to get on the show. And me and another comedian, Andre, we drove to New York. We missed the audition at the Peppermint. By an hour, the Peppermint had closed. And I remember we came back, my cousin Baby Doll and my other cousin Ernest Lee took me to the Peppermint Lounge. And my cousin Baby Doll worked for Hush Production, that's Melba Moore's company management company with Freddie Jackson in them. So we get there, I think I'm a bomb. Cause Marvin Dixon gets up and, you know, he does that Jamaican dance. Our girl tears the room apart. Bill Bellamy brings me up and they tell me to do seven minutes. I think I ended up doing because I think I drank about a triple shot of gin meat. Triple shot, me. And I just went on autopilot and I did 10 minutes of political humor and 10 minutes of sexual and spiritual humor and got a standing ovation. And that's When I got Apollo Comedy Hour uptown and Def County Jam. Same day, same night.

[Shannon Sharp]

You mentioned about all the. Okay, you working 8 to 5. You work at 8 to 5. You kept your clothes in the car. You go do a gig, you drive to different cities than you do in other gigs. You sleep in your car. You're highly educated. You got multiple degrees. The grind. A lot of people don't want to grind like that. Especially, man, somebody just need to give me a job. I got all these degrees. But that wasn't your thought process. You like, hey, I'm gonna grind. I'm gonna make it. Even though I have all these degrees. Yes, I know the grind. I know what it takes.

[Cheryl Underwood]

Oh, I'm grinding right now. The talk is off the air, but I wanna take that experience to produce content. Movies, unscripted everything. TV shows. But you got to have that grind, because you gonna get no more than you get. Yes, yes. And people are dependent on me. My sister depends on me. My disabled sister is depending on me. So I gotta make this work. Where does she go if something happens to me? Now, would I like to have a man by my side that helped me build and run this empire? Hell, yeah. But the average man, and this is what we hear, you're intimidating. I don't know no true man, no hard leg dude is intimidated by a 52 woman that talk for a living. Am I right?

[Shannon Sharp]

No.

[Cheryl Underwood]

Okay. Why am I not right?

[Shannon Sharp]

No, I'm not saying you're right. Because he shouldn't be. Because if he has his own, why is he intimidated by what you're doing?

[Cheryl Underwood]

And he don't have to have his own. He can work at the damn gas station. I know I'm gonna get free gas and honey buns and Doritos and all kind of if my man work at the gas station.

[Shannon Sharp]

But here's the thing.

[Cheryl Underwood]

What?

[Shannon Sharp]

The way we were brought up is that the man takes care of the house.

[Cheryl Underwood]

Mm.

[Shannon Sharp]

The woman doesn't take care of the man. I don't probably. You grew up in Arkansas, if I'm not mistaken. I grew up in Georgia.

[Cheryl Underwood]

Yes.

[Shannon Sharp]

And every situation that I saw is that the man, My uncle, my grandfather, everybody that I knew, the man ran the house. The man took care of everything. And so to have it. The flip side, I don't know. A lot of times, men, ego and their pride.

[Cheryl Underwood]

Well, here's what my dad told me. He said, listen, son, he said, you're gonna have a problem because a man goes to work Monday through Friday, get his check, wanna take his gal out for dinner or a movie or something and go to church on Sunday, you will be working those days. But if a man truly, truly looks beyond that and see what we can build, young or old, what you can build with a woman by your side that understands I'm. That when I'm working, when I come home, I'm going to fix the meal, I'm going to fix your plate. I don't eat before a man eat. I did not eat before my father ate. A lot of women go, you stupid as fuck. No, that's just the way I was raised. Respect for a man. And if you are a real man, you will understand. I'm not out in these streets doing nothing. I'm not going to different cities doing nothing. What I want is a man by my side that will help me build. And that's what I'm looking for. And I think there's a man. There are men out there that I think would be with me.

[Shannon Sharp]

Right?

[Cheryl Underwood]

The only thing is, if you think that's what I am, if you think I'm argumentative because I'm so good at what I do on stage, then get to know me. That's the biggest problem. We don't get to know each other. And then I think sometimes as women, we so used to being a man and a woman in our relationship, we.

[Shannon Sharp]

Don'T know how to fall back and just be the woman.

[Cheryl Underwood]

There you go. And I know how to make a sandwich. You want cheese on your sandwich? What you need? What you need? I know what to do. I want to pick up the dry cleaning. I want to do what I saw my mama, Mama who raised me and who was married to my father. I want to do what they do. I want to be the wife while I go out and slay a dragon. We back to back on slaying these dragons. That's what I want, want. So how can I find it? And who are you call right now? Don't y'all have a toll free number?

[Shannon Sharp]

What we gon. We gonna put one up at the end of the show.

[Cheryl Underwood]

Put one up at the end of the show. That's why the tour is called the Mix and Mingle tour. Because I want people to mix. And there are a lot of lonely people out there. But you know who's lonely the most? Men. Men who don't want to take the chance of getting to know a woman and saying, that's, that's my girl. That's what I'm looking for, you know, so why not? And if you can take me without A wig and makeup. Cause I look like George Jefferson without. If you can take that. If you can take the fact that all I want to do is watch the news. I watch sports all day long. I watch news all day long. I watch old movies all day long. But I'mma do what I need to do as a wife and a woman that love you. But I work around guys. Ain't nothing happening. I don't who I pay. What kind of dumb is that? You think I'm this dude? Over. Well, yeah, Come and get it. Come and get it. Get this money. Get this money. Your job is not over. Come get this money, son. She's not as bad as she thinks. Usually I tell people, I tell, you know, ask me when we get to dating, we need to talk about dating. And maybe I'm doing it wrong. Maybe that's where I'm up. You think? Cause I will tell a man, you know, whether I'm giving up some ass or I will tell him, you know, it's not gonna be as great as you think. I got one good move. One good. One good. No, I got one and a half. One and a half. I do one thing very well.

[Shannon Sharp]

Yeah.

[Cheryl Underwood]

Why you frowning?

[Shannon Sharp]

I ain't frowning.

[Cheryl Underwood]

Cause you could have had it, but your ass jumped out the car like you was. You jumped out the car like you was on the Dukes of Hazards or some kind of. You did jump out the car fast.

[Shannon Sharp]

Cause it was midnight. I gotta go to work the next morning.

[Cheryl Underwood]

You was gonna sleep wherever you was. I was gonna drop you. I got one good move. I was gonna drop him. That.

[Shannon Sharp]

No, but I mean, I'm old school, Cheryl. You don't do that on the first date. On the first night.

[Cheryl Underwood]

We had been talking from one night to the next night. Remember you said it's midnight, so it was two nights. It was two nights. You need to pay attention. See, I had a strategy, ladies. I had a strategy. I'm gonna talk him all the way till he got too sleepy to drive. That's it. What?

[Shannon Sharp]

Do you remember your first time on stage? The very first time you got on stage.

[Cheryl Underwood]

You mean paid as a comedian or just on stage?

[Shannon Sharp]

Yeah, getting paid. Your first gig?

[Cheryl Underwood]

Oh, probably was the Humminbird in Chicago. But I have been doing comedy everywhere. I've been doing comedy in high school. I was the rally commissioner at Warter High Castle Air Force Base. And I somehow fadangled my way into being the rally commissioner. And there were big productions. That's when I knew I wanted to produce content. We as the falcons we weren't winning the game. You know, Merced High School was always beating us. The Bears was always beating the Falcons. But the rallies were low attended events. When I became rally commissioner, everybody was getting up early in the morning to come to rallies because I was doing comedy. I had music in it, dancing. I had at least 500 people in a gym. Wow. Every Friday when we had games. So that's when I knew I could produce. And it was funny. My principal, Mr. C.J. groves, he said, you know, you're very, very funny, honey. Don't let these young people pull you down the road of blue adult comedy. In my mind, I was thinking, it's too late, Mr. Grove.

[Shannon Sharp]

I'm already there.

[Cheryl Underwood]

I'm already there. Because who I loved in comedy, the Richard Pryor, the Pygmy Markhams, the comics that I loved and wanted to be like. I wanted to be Gregory Richard Pryor, but I wanted to be some of those comics that I want to be able to talk about anything anyway, with a language that the street will understand and bring people together at the same time, even if you disagree with me.

[Shannon Sharp]

Miller Comedy Search.

[Cheryl Underwood]

Yes.

[Shannon Sharp]

How did you get discovered for that?

[Cheryl Underwood]

We heard that there was a competition, and they didn't. Normally you don't have a lot of females in the competition. And I remember that was where I met Damon Wayans.

[Shannon Sharp]

Okay.

[Cheryl Underwood]

And he was a great mentor for me. And he was trying to produce a sitcom for me to be in. And all the males who understood what I was trying to do, they always encouraged me. When people say, well, do you think it was hard for you? Cause you was a female? No harder than it was for anybody else. You had to be funny. Did I think that it was gonna be an easy way? It wasn't an easy way for a lot of people. Ask Kevin Hart, was it easy for him? Ask Steve Harvey. Was it easy for him? Ask Cedric. Ask Chris Tucker. Was it easy? When you get the opportunity, you gotta be ready for the opportunity. So getting the Miller Lite Comedy Search, even though I did not win, I placed enough to be respected. So if you look at the history of comedy, the great comics sometimes do not win comedy competitions.

[Shannon Sharp]

Correct.

[Cheryl Underwood]

They may place or they may come in dead last. And it gives them that drive to go, oh, I'm gonna come back. I was in the Bay Area Black Comedy Competition, I think three years in a row. I placed in the top five three years in a row. And I was told that a woman will never win it. Okay, cool. I ain't got to win it all I need to do is win over the audience, and that's what I need to do.

[Shannon Sharp]

That's what you're trying to win.

[Cheryl Underwood]

That's right.

[Shannon Sharp]

I'm trying to win. Damn the competition. If I win, the audience, they're gonna come see me at a later date and time somewhere.

[Cheryl Underwood]

Oh, I like to win competition. When we won an Emmy on the top, I was like, ah, yeah, that's what I'm talking about. When we won the NAACP award, I was happy about that. Winning competitions is. It's the cherry on top of. It's just like you win in Super Bowls.

[Shannon Sharp]

Yes.

[Cheryl Underwood]

It's the cherry on top.

[Shannon Sharp]

Everything you have, it's the validation of all your hard work.

[Cheryl Underwood]

That's right, that's right. That's right.

[Shannon Sharp]

But in 1989, you were the first female finalist for the Miller Light Comedy Search.

[Cheryl Underwood]

Absolutely.

[Shannon Sharp]

What do you remember most about that experience? Because you said, although you didn't win, you got some great mentorship from Damon Wayans, but it drove you because you had won the audience. Because even though you didn't win, you felt you won the audience, that at a later date and time when you got your own thing, they gonna come see Cheryl Underwood.

[Cheryl Underwood]

Absolutely. And the fact that I could bring men and women together in the beginning, I was telling so much, so many sexual jokes, women was popping out of my show like the Great Pumpkin. I'm not doing that with no man. Well, that's why your man looking up here at me, and I ain't the finest broad in the world, but I'm the most focused. I'm gonna do what you don't do. Well, while this is a part of my personality, it is the type of material I love. To do adult comedy, to me, you have to be a really good comic. That can come from adult comics to clean comedy. Clean comedy. If you look at. What's the guy named? Bob Saget. Yeah, Bob Saget and I, when he was alive, God rest his soul. Good dude. But we would talk about adult material being in daytime, us being in daytime, and family stuff. But the most fun is to tell an adult sexual joke. Why? Because there's only two, maybe three ways to have sex. Four, if you're really creative and short on the phyto, it's. It's only a few ways to do it, but to be able to talk about it humorously and make everybody laugh. See, I'm doing political material, but what brings the audience together? Sexual relationship material. And that's what does it.

[Shannon Sharp]

Bernie Mac, Adele Givens, Cedric the Entertainer, were also participants in the Miller Light Comedy Search. Did you have interaction with those?

[Cheryl Underwood]

Absolutely. I remember talking to Adele at. On the west side. I think they did a round of the Miller Light county search in Roses. And she was like, I want to do what you do. And I remember that night because I was going through things in my marriage that night. But I always knew my father said, nobody cares about what you're going through in your life. You are the entertainment that they paid to see. So swallow all of that and get your. You hear me say swallow. Swallow all of that and get yourself together.

[Shannon Sharp]

Right?

[Cheryl Underwood]

So that night, I remember meeting a dad. She said she wanted to do it. I said, do you? They can't steal you. They can't steal your life. And don't let nobody tell you you cannot do it. And people say, well, what do you feel about other female comics? I want us all to win and succeed. I want us all to make movies. I want us to do sitcoms. I want us to open the door for each other. Monique is one of the greatest actors. Not actress in my. But actor. What that did in Precious. Precious, listen. Listen to me. When I saw her, I said, I want to fight you so bad. Because everything I've gone through.

[Shannon Sharp]

Because you were so nasty to Precious.

[Cheryl Underwood]

Yes, but everything I had gone through in my life, molestations, rape, everything that I could see that person, you know, And I've been around that person. I've lived. But that girl is such a talented. That woman is such a talented actor. When you're talking about the skill of Samoa, the skill of Adele, the skill of Tiffany Haddish, the skill of all female comics. But why are we not making movies? Why aren't the guys that can do it, Kevin can produce. Why aren't they producing us together in something? And we've got to put aside any differences that we have for the greater good of us. Getting a bag for our families, our mortgages, our children going through college, our retirement, we need to come to.

[Shannon Sharp]

Right. Bernie Mac, the legend. Everybody speaks nothing but highly. He's held in the highest, highest regards.

[Cheryl Underwood]

Absolutely.

[Shannon Sharp]

What do you remember about your interaction with Bernie?

[Cheryl Underwood]

I knew Bernie when we called him Blue. Cause he was so black. He was blue. And he was friends with Denavius Cobb on the street that we lived on in Chicago. She lived across the street from us. And he was always a family man. Integrity, a good guy. He was like the father figure to us, like the older brother figure. And he would ask truth, why you don't dress up on stage? I Said, listen, let me tell you something. If these jokes ain't funny, it don't matter what I'm wearing. Right? Right. But I would always take his advice and counsel. I'm kind of feisty, you know, I say, I am my mother's daughter and my father's son. So I'm gonna talk back to you. Cause that's what my mama did, you know? But Bernie was the kind of guy that if he felt he could help you get that joke tighter or advance your career, he was that guy. And maybe I'm kind of. I don't know if you're this way, too. I'm kind of reclusive. Would you say I'm gregarious when I need to be gregarious? But most of the time, I'm private and I'm reclusive.

[Shannon Sharp]

I tell people. I explain myself to people like this. I'm the most outgoing introvert you're gonna meet.

[Cheryl Underwood]

There it is. Me, too. Me too. You're not gonna know too much about me. You may have shaken hands with somebody I dealt with. And I'm not gonna disrespect you or him. You know, I just don't. I talk for a living, but I don't talk about everything.

[Shannon Sharp]

Def Comedy Jam, that was the pinnacle, Martin. And so many of the comedians that we see today, they got their start there.

[Cheryl Underwood]

Yes.

[Shannon Sharp]

Do you remember much about that?

[Cheryl Underwood]

I remember driving to New York, staying with my cousin Ernest Lee and my cousin Christina, and. And going after I got Def Comedy Jam, they asked, could you stay over and do Def Comedy Jam? And when I. They said they would give me some money. Cause I didn't have any clothes. So what you see me wearing, that little bitty orange shirt and them stretch pants and them boots, them superhero boots that I was wearing. That is what I wore to drive from Los Angeles to New York.

[Shannon Sharp]

Wow.

[Cheryl Underwood]

Because I couldn't find clothes and what money they giving me. You know, when you don't know a city, you don't know where to go down to the alley or down to the. You know, the place to get a $5 shirt and some $10 slacks. You know what I'm saying?

[Shannon Sharp]

Right.

[Cheryl Underwood]

So what I'm wearing is what I'm wearing. And then I remember they would do the walkthrough. But when I came to do the walkthrough, I could hear people whispering, that's her, that's her. That's the girl that tore up the peppermint. That's her. That's her. So we get there, and Martin is reading the. Reading the script on what they're gonna say. And so they asked you, what is your first joke? What was your last joke? And I think my first joke was two drinks. No, either. Bitches ain't need to suck my. And damn sure. Yeah. Yeah. And it was two jokes. First joke, last joke. And everybody was laughing. They were like, snickering. And then I said, Martin, I said, Mr. Lawrence, because I had seen him perform. I watched him do a show in Chicago. Adele Givens, Martin Lawrence, and Chris Rock. One of the greatest shows I'd ever seen, right? So I said, martin, I said, can you just change? Because they had me from Chicago. I said, can you just change? I live in Los Angeles now. And he was like, okay, cool. So it was asked of me, why? And I said, because if a promoter is looking for me to book me, I need him to know where I am. Because I'm always about my money, right? I'm always about my business. I'm about my paper. And I had to learn that night pacing because I was gunning them jokes. Pow, pow, pow, pow, pow. But I was gunning them so hard that people have to take a time to breathe. And once you learn that technical skill of how to do a TV show, then you can always clean it up. So when I did Showtime at the Apollo, oh, they was getting ready to boo a sister. And I had the flu when I did Showtime at the Apollo. But I was determined, you are not going to boo me. I'm going to get to these jokes. So by the time I get to the things that I've done where my set wasn't great, it didn't bother me when I did Indecision 96 with Bill Maher. They wanted me to only talk about being a black Republican, but there's jokes above and below that that you have to do. So I love the fact that my career is always a work in progress. Even now. Even now. The Sheryl Underwood legend is what fuels me to always be a good comic and understand. What did it say? Any given Sunday.

[Shannon Sharp]

Yeah.

[Cheryl Underwood]

Any given stage time. You may not get them that day, but you better have some jokes that always bring them back to you. So Def Comedy Jam. And that was also the first time that they told me I couldn't take my purse on stage.

[Shannon Sharp]

Yeah. Cause tell people you explained to me. I kind of know the backdrop of it. And I wonder why you ain't got that cheap ass purse that you had at this liberal. It ain't here, it ain't here. It ain't Here we got over there.

[Cheryl Underwood]

And what cheap purse are you talking about? And that's why that dude in Burke. Well, listen, that's why I still have money. I have purses. Like I have boxes of really classy Louis Vuittons. And was it Louis Vuitton, Louboutin or however you pronounce this? But if you spend all your money on that, you will not have money, right? My little Ponderosa is paid for. If I get one good income tax check, my car will be paid for. What is my debt? To make sure my sister has 24 hour cap, right? So I can adore myself. This is a synthetic Amazon wig. Look good, don't it? And it's anchored down. But I have custom made hair. I have the finest of the finest for my wig. But I also know how to manage my money. How to manage my money. And I want to make some more of it too. But you asked me the question about the purse. Really, it was a feeling of not just security, but when I finish what I'm doing, I'm going to walk out of the venue. I saw Richard Lewis when he was alive. Great comic. He would only come into the club when it was time for him to perform. You know, I watch all comics. Mitch Hedberg, oh my God, in love with Mitch Heberg. Thought I was going to marry him. I watch all comics to study them, to study their greatness. Marsha Warfield, she had a skill that I wanted to learn how to do. So when you're talking about telling jokes. Yeah. The joke is, why do you carry your purse on stage? Because white folks steal any race of people. Take land from the Indians or show enough, take two or three dollars out your purse. That's a joke. Yeah, that's right. It's a joke. And the second joke that goes with it is I fear for my life when I'm. When white people get on the elevator. Remember it was when we get on the elevator. That's right. So I reversed that. When white people get on the elevator, I grab my purse and call out for the law. Jesus, just let me make it to the lobby. Those are jokes that you can reverse, right?

[Shannon Sharp]

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[Shannon Sharp]

You got the gig at Comic View. You were the host.

[Cheryl Underwood]

Yes, but I had lost it.

[Shannon Sharp]

Yeah.

[Cheryl Underwood]

Remember, I had lost it, I think two times. Did I lose it two times. But I was not mad. I think it was, what's the baby name, young lady? Montana Taylor. Montana Taylor won and some more won. Yes, right. And people say, well, are you against female comics? No, I support female comics. But like the Bible say, everything ain't your time, everything ain't your season. I just had to learn how to pull myself together and go, okay, go back up to bat again by the time I got it. Because people didn't believe that these Sheryl Underwood could do a clean set. They didn't believe it. They didn't believe the material that I was doing. I was out there telling O.J. simpson jokes long before anybody else. I was telling, God rest his soul, Kobe Bryant jokes, but I was telling from a different point of view. Matter of fact, I did Midsummer Magic. Remember, Magic Johnson used to have Midsummer Magic out in la. And I was telling these jokes from a different position. I wasn't trying to hurt Kobe's family. It was that I knew that I wanted that humor to come off, and I put it in a direction I felt that it should go. It wasn't all about him. It was all about a setup, you know, and those jokes were getting standing ovations. O.J. simpson joke. Cause we really wasn't cheering O.J. we was cheering Johnny Cochran because we needed somebody. And now who do we have now? Ben Crump. When Ben Crump show up. Matter of fact, you and Ben Crump need to do a move and a talk show. Cause both y'all some thick tongue talking intellectuals.

[Shannon Sharp]

Big got that money, though. Listen, he got no bread.

[Cheryl Underwood]

He ain't got no money.

[Shannon Sharp]

I ain't got nothing. He got it.

[Cheryl Underwood]

You better know it. You better get with. Y'all could play brothers in a movie. That would be cute. And then had y'all as little babies. And y'all whine and cry with a thick tongue. And then y'all grow up. Tongue just a thick. Make a lot of money. That would be great.

[Shannon Sharp]

I might look into that.

[Cheryl Underwood]

Look into.

[Shannon Sharp]

You think I could be in that?

[Cheryl Underwood]

Hell, yeah. Hell, yeah. You know what I'd like for. Okay, one thing I don't do? Devil worship. That's why I'm not an actor. Now people say you act. I was in Beauty Shop. And I almost didn't get that. I almost didn't get that. Let me tell you something. We had heard that they were looking for a Cheryl Underwood type.

[Shannon Sharp]

Well, damn, why'd I get Sherry Underwood?

[Cheryl Underwood]

That's what the I said, right? So I got my happy ass on the plane, flew back from the gig in Orlando, went in and auditioned and got the job. And matter of fact, it was Sherri shepherd who. You know, she knew how to do movies, right? And one day I went to her trailer, and I just burst into tears. And she said, what's wrong? I said, everything I'm trying to do, either they've given it to somebody else or they don't want to do it with me. I said, I don't know how long I can do this. Maybe I need to go teach school. And we both got on our knees, and she prayed for me that day. And that's when we went out to do the scenes. And you remember when I said monkey bread? Cause I was catfish reading with the monkey bread, and it made everybody laugh. And Queen Latifah said, okay, you can keep doing that. And then they kept writing a bigger and bigger part for me. And that's how I get it.

[Shannon Sharp]

You negotiated comic. They was getting a thousand dollars instead of a hundred. Why did you feel you need. At that moment? This was what Cheryl Underwood needed to do.

[Cheryl Underwood]

We had heard that there was discussion. I think it was Comedy Central with the white comics. And in these meetings, there were Black comics going, well, what about Comic View? And being in a Greek letter organization, we know parliamentary procedure, we know meeting structure. And so when we went to the meeting, they said, well, you black people handle that, right? So we go, okay, we're gonna handle that. And in the discussions, we put together our committees, we review laws, you know, see, that's why a college education. And if you went to a hbcu, you really got a good education. You got life and education.

[Shannon Sharp]

Correct.

[Cheryl Underwood]

And culture. So those of us that were in Greek letter organizations and went to College and in HBCUs, we came together to form a sub, unofficial subcommittee. So when it came time for certain things and we had Tim Allen signing our petition in Variety, Jay Leno, we had the comics backing us, big time comics backing us, when all we wanted it to be fair. But there was one thing, one line I said, I will not cross. We will not picket Bob Johnson at bet. We will not do that. We will not give them the photo opportunity of us against another black man, Right or wrong. I just didn't feel that that was the right thing to do. And I felt that he would do the right thing. And he did.

[Shannon Sharp]

Wow. People run up on stage fighting comedians. Ms. Pat says she done fought comedians before. Where are you? I mean, somebody. Has anybody ever run up on stage on. You got mad that you were saying something during your set. Has anybody ever got mad at you? Sheryl?

[Cheryl Underwood]

I was in Monrovia, California, and, you know, I didn't know what kind of location Monrovia was. This is kind of location that you don't see a lot of us in, you know what I'm saying? This is long before Trump was making America great. This is long before. So I was booked to do a gig. I did the gig, and I guess a white man didn't like what I was talking about. And he threw a beer at my head, and it passed my head and bust on the wall, and it was beer splattered everywhere. But I'm going to tell you where a well placed joke goes. I was telling so many good sexual jokes, other white boys whooped that dude's ass.

[Shannon Sharp]

What?

[Cheryl Underwood]

Yep. Whooped his. And then went, finish your show. Good comedy is still good comedy if you would just let us get to it. There are people that disagree with me on my political stances, or they may think that the show is too sexual. But once you walk into a nightclub, a comedy club. I'm doing Harris. I want to do all casinos. I want to do all comedy clubs. Not just for the money, but for the career. And so when you come into a nightclub experience, my job is to move food and drinks and entertain and not let people get up and walk out. So I will instinctively scan the audience to see what's going on. That's why I have two male acts with me, Kyle Irby and Mike Washington. Why? Because I don't want a man to come into my show and go, oh, here she go. It's an hour and a half and niggas ain't. That's not what my show is about. It is a love fest. It is a party. It is a house party. It's me talking like we talk. You know what I'm saying? And having a good time. And then at the end, guys get up, you can walk across the stage, and you might win my money. That's why we mixing and mingling. But I will say this. The people who have been upset with my show, I've tried to polish my performance to a point where you go, wait on me. Something in my set you're going to enjoy. Just wait on me. Hold on. And do I need to buy you a drink? Because I was lighting white women up. I was lighting them Beckys up. And I saw you talking to Darnell Rollins about, does he date him? Is that what he doing?

[Shannon Sharp]

I think so.

[Cheryl Underwood]

You think so?

[Shannon Sharp]

I think. Listen, I don't know. I think she might be, like, Latino or Hispanic or something like that. I'm not really sure that's one of us.

[Cheryl Underwood]

That's brown. That's brown. That's brown on both sides. Black and brown. But my thing is, I think we should let our men date whoever they want to date. If that's what you like.

[Shannon Sharp]

I like who like me.

[Cheryl Underwood]

That's making. That's how I feel. When I was dating white men, do you think I sought them out? No. White men want to date the darkest of us. Cause they feel like that's the uncut. That's the bomb. Right? I'm not saying that that's what I want to love. I mean, in dating them, it was a feeling that I had, but I wanted to be with who wanted to be with me.

[Shannon Sharp]

Yeah. I mean, what's wrong with that?

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[Cheryl Underwood]

Okay, ladies, when I said we came to play, didn't I mean it? This Disney cruise got me feeling like a queen. We can get massages at sense of spa, have a meet and greet with Black Panther. Oh, I love him. And I can't wait to sunbathe on the private island. And the kids will be fine. Girl, they're good. Exactly. While they hang in the kids club with Mickey Mouse, we can do our thing. Mm. And do it all day. Disney Cruise Line is where we came.

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[Cheryl Underwood]

That parents rank financial literacy as the number one most difficult life skill to teach? Meet Greenlight, the debit card and money app for families. With greenlight, you can send money to kids quickly, set up chores automate allowance and keep an eye on what your kids are spending with real time notifications. Kids learn to earn, save and spend wisely. And parents can rest easy knowing their kids are learning about money with guardrails in place. Try Greenlight risk free [e-mail] iheart I would say there is something wrong when it only goes to the bedroom. Why do you only like me sexually? You might like me intellectually and sexually. And I've been in situations where white men. Well, I'm taking you to the country club and you're gonna go to country club. I don't want to go to country club with you. Why? I'll meet you at the 19 hole. I'm going to sit down. You know what I'm talking about. I play golf to enjoy the course, right? I'm not a great golfer. I just want. I hit it where it land. If I really get my game together, I can do pretty good. But I don't really play golf to talk to people. I play golf to enjoy the course. But if you taking me to the country club just to show how liberal or progressive you are. That was an uncomfortable feeling for me. So if you were a Latin man who was in love with me. I've had a lot of crushes in my life. Latin men, white men, Asian men, all kind of men, black men. But that's what I love. That's what I think understands me. Understands when things don't go well. But I've sampled everything God had made on the buffet of love. But I'm not against our men dating outside of the race. What I'm against is when you down us to uplift somebody else. And that's why I was telling those jokes where you get the worst that you can find. But I can't be what I am. I'm too talkative, I'm too ambitious, I'm too strong. I gained five pounds. You don't with me, but you get with Becky. That's two sizes of me. And you sit, remember? What's the show? Where is it? Maury.

[Shannon Sharp]

Maury Povich.

[Cheryl Underwood]

Oh, listen to me. It's always a brother on there. Well, what if these are not your children? I'm a loam lighting.

[Shannon Sharp]

I've been in these kids life. I'm the only dad. They don't.

[Cheryl Underwood]

They look just like me. Look, they got my eyes, they got my nose. And this girl is the worst of the worst of the worst. If you gonna get one of them, get Taylor Swift, don't get the worst one. I'm not against you white girls pulling our man, but some of these girls, I just wanna look at a brother and go, I see it.

[Shannon Sharp]

I see why you got it.

[Cheryl Underwood]

I see why. That's right. That's. That absolutely right. Get her together, put this on a treadmill, do something. Get her to eat some vegetables. Or don't get the worst of the worst. And then throw it in my. That's what I don't like. And I don't think most black women like that either.

[Shannon Sharp]

Let me ask you this. If I had said, okay, Cheryl, give me your goat comedians. It could be male, men or women. Give me your four comedians that you would consider Mount Rushmore too many to name.

[Cheryl Underwood]

And because of my personality. Why she didn't name this person? Why she didn't name.

[Shannon Sharp]

There's your name.

[Cheryl Underwood]

Well, I don't really have. First of all, you're gonna have to have a bigger. It's gotta be a mountain range. It can't be just four motherfuckers on a mountain. Cause there's too many of us that are too good for too many time. Periods. When you talk about Moms Mabley, one of the greatest female comedians, that made people feel good about all those adult jokes she was telling. But then you put up against Whoopi Goldberg, who was. To me, her dialogue was so amazing. Her ability to go in and out of characters, so amazing. But I don't want anybody to feel I like somebody more because I can't do what Sherri shepherd do that. And I'm sorry, girl. Cause I know there's some comedians don't like to be called bitch, but I gotta give you a propers. And speaking of that, Melanie Camacho, one of the greatest comedians I've ever seen. Hope Flood, greatest comedians I've ever seen. There's too many out there to name, and we haven't gotten our shot. So that's why I want to produce something that gives people their shot. Who would have thought somebody would have called me to be on daytime tv and I'm a nightclub performer, and I'd be there from season two to season 15 of the Talk on CBS, the most conservative network. All we need is the shot. So in answer to your question, there are too many great comics that you see these comics, and we've been sitting around with each other. You know how hard it is not to choke laughing at Jamie Foxx when he gets on a roll. And all of us have been friends, but then we talk about him when we show the picture of him with the Jheri curl. That's comedians getting, you know. So I really couldn't name, you know, who would be my top.

[Shannon Sharp]

Let me ask you this. Are there. You mentioned Hope Flood, yourself and Some More, and Adele Givens and Chocolate. So many of the young. I remember so many of the women comedians back in the 90s.

[Cheryl Underwood]

Yes.

[Shannon Sharp]

Are they an upcoming crop of new women comedians?

[Cheryl Underwood]

I think all these young ladies on social media, they got one coming. Don't call me a white girl. I think this got a line. I ain't gonna say it. Cause I want y'all to hear it out her mouth that I was hosting a show in Pennsylvania, and when she dropped that line on the people, I ran out and tackled her. Cause it was such a good line. I'm a technical comic. I will listen to somebody single. Damn, I wish I had wrote that. You know what I mean? So there are some great female comics, but also, you need time. You can write jokes every day. You can't polish every day. You need stage time. You need to understand why those of us that were doing adult, we're doing adult comedy. And don't separate, don't say, well, this is a clean comedy. Are you a good comic? Right? And then there are comedic actors who are decent stand ups. That's why I'm not gonna name names. They know who they are. You're a decent stand up, but you're a great comedic actor. So don't push.

[Shannon Sharp]

Are they two different things?

[Cheryl Underwood]

Yes.

[Shannon Sharp]

Guys that can act in front of.

[Cheryl Underwood]

And be funny, be funny in front.

[Shannon Sharp]

Of the camera as opposed to getting up there and it's just you and an audience and a microphone.

[Cheryl Underwood]

Absolutely, absolutely. And I'm gonna tell you, when people say, like, I don't know why Earthquake has not been put in a position to do a recording of Sanford and Son, I would be honest. And all you're doing is picking up junk, right? You can do that today. D.L. hughley, great comic. George Jefferson. Today you can do these things. Now why is it that they get to reboot everything and we don't? You can do. That's my mama. You can do what's happening, which is nothing but Cooley High. You can do this today. We need the opportunity to do it. And there's some great comedic actors, but we need the directors, we need the producers to be able to take what we're already doing in our head. See, a standup comic is the writer, producer, director in their head, right? And the performer. We just need to be able to be produced in a way where we're confident in what you're doing. Cause I already know what I can do for myself. How do I get confident enough to do it on screen and not want to turn to the audience? And that's where your cameras are. You're acting with the person. You're reacting to the person. And I know what you're thinking out there. You can be an actor. You saw me and I got the hookup. You know damn well I didn't have no business. But that was Master P. And I'll tell you a story about that, too. A.J. johnson, God rest his soul. Little aunt. Me and aunt, we're good friends, right? So he's talking about Master P got this movie, right? And so I was taking care of my sister, and I couldn't find a caregiver and everything, so I had to go to the audience. I took my sister to the audience, you know, disabled people. She in a hot car, so she fighting, pulling everything, pulling hair, everything. I said, you gonna sit your ass right down here so I can go up here and get this job, right? So I get up there and there's a line and everything. And I said, listen, I need to do this right now. I. I said, who the is Master P? Now? I don't know who he is. I said, who the is Master P? So he's me. I said, what the is? Nah, nah, nah, nah. There ain't no lyric. DJ Quick, Kumo D, them lyricists, those rappers, producers, everything. What the is that? So he's laughing because I'm talking to him the way I'm talking to him. And they write a whole new part for me to do this. And that's the second time it happened. The first time it happened, I was performing in the Melrose Improv and I was there to showcase for Brandon Tartikoff when he was alive. Brandon Tartakoff is who? How? Eddie Murphy. And okay, so I'm there to showcase for him and he tells me, I see you walking in on the scene in the sitcom, throwing up the joke and walking out like Marla Gibbs. See, you're talking about a comedic actor, great woman, right? So I was like, oh, you really do that. So when it's my turn to get on stage, I get on stage and I see Annette Benning and Warren Beatty sitting in the audience. So I start telling these jokes about Bugsy. You know, when she threw that ashtray at his head, I said, you black? I said, only a real sister throw a motherfucking ashtray with a lit cigarette in that mother as head. So I'm telling all these great jokes. So one baby comes out making a movie, gives me all his information. I want you to come have a meeting with me. I'm making a movie, I want you in it. Now how many times have we had boys and girls? So I go, all right. So I take the information and something led me to call him and he goes, I want you to come drive up on Mulholland. You know, I'm not the greatest driver in the world, you know, so. Cause if you don't shift right, you're gonna roll all the way back down.

[Shannon Sharp]

Yeah, you absolutely.

[Cheryl Underwood]

Am I right? So I go to the meeting. We're talking what I thought was a 15 minute general meeting. We end up talking about four or five hours like me and you did in the car. We ended up talking four, five hours about pop politics. I'm a registered Republican who is really a conservative Democrat. He is a liberal Democrat. We're talking, but he's remembering things that I'm telling him and he's adding them to his script. So we're talking then the part that they wanted Me to play. I think I was supposed to curse in a church. I did not know. You're not supposed to tell the casting director. I'm not doing.

[Shannon Sharp]

No, you can't do that.

[Cheryl Underwood]

Okay, why am I not supposed to tell them that, Shannon?

[Shannon Sharp]

Cause they're the one that's gonna get you the job.

[Cheryl Underwood]

Well, I'm sorry. I fear God more than I fear man. God don't know I'm down here doing a movie. God, looking down, going, what? You know, why is she in my house Cussing, Right? So I told him I wasn't gonna do it. I said, I'm not gonna do it. I said, and no self respecting black person will be cursing in their neighborhood church. I'll cursing the parking, but I'm not cursing in the sanctuary. It's not going to happen. So they write a part for me. They write a whole different part for me where the white dude, I think his name is Oliver Platt, he's an actor, he's supposed to bump into. I think he was in A Time to kill with Matthew McConaughey. Okay, so he bumps into my arm and I'm supposed to say, break yourself, fool. Which I don't know who came up with break yourself? I don't know. Nobody's stream. Okay, so did he come up?

[Shannon Sharp]

He's the first person I heard say it.

[Cheryl Underwood]

Really?

[Shannon Sharp]

Okay, then maybe Smokey said it.

[Cheryl Underwood]

Okay, so break yourself.

[Shannon Sharp]

Break yourself first.

[Cheryl Underwood]

Okay, so he. That's the line I'm supposed to say, but I can't get it out the way they want me to say it. I keep saying, excuse me. So. Because that's the way I was raised. This supposed to be an after hours, private black club with some white people in it. So obviously you must be guests of somebody in this club. So Warren Beatty directing, you know, he, he goes, cut. Cheryl, I need you to talk the way you normally talk. I said, what is that? And he said, I need you to be more animated. I said, really? And he said, I need you to be more profane. Why? I said, you believe that black people only settle their differences with profane language and animation. I said, that's not true. Now remember now, all of the extras are black, right? So they all looking on the ground like, oh my God, this is talking back to Warren Beatty. I said, I'm sorry, that's not how this goes. If he bumps into my arm, knocks my drink out my hand, I would expect to replace it with a higher level on the shelf, top shelf drink, right? So people are trying not to laugh. So Warren Beatty goes, but what if I called your mother a. I said, what'd you fuck. What'd you say? He said, what if I called your mother? And he names my mother, uh. Oh, he names my mother.

[Shannon Sharp]

Hey, I bet you got in the wrong. I bet you got in the character then.

[Cheryl Underwood]

Listen. I said, listen, I laid that motherfucker out. I said, I don't give a. About splinting the grass reds. What did Bonnie and Clyde. I said, if you ever say my mother's name and in a sentence ever again, I'm gonna jump across this camera and whoop your ass. And he goes, I need you to do that right now. Action. And that's when I did it. That's when I did it. And we became friends. And we became friends.

[Shannon Sharp]

That day you did radio with Steve Harvey. What was that experience like?

[Cheryl Underwood]

Well, really, how I started. It was Tom Joyner.

[Shannon Sharp]

Oh, really?

[Cheryl Underwood]

Yeah, it was Tom Joyner that gave me one of my first consistent radio jobs. And then I wanted to. I want to do radio. Like, if we really do a podcast together, I want to merge it with terrestrial radio. I do not believe you can do anything without radio, because black people do not believe that Jesus is coming back until they hear Black Ray. Am I? And it's still in your car, and it's still in your homes. And I believe that we can do some good merging podcasting with radio to build that audience. So Tom Joyner gives me a job, then Rashawn McDonald and Steve Harvey say, okay, why don't you come work over here with us? And I go where the money is. It's no dislike of anybody. No dislike. Matter of fact, would you be willing to bring your podcast on the fantastic voyage, the Tom Joyner Cruise? Would you want to so we can benefit some HBCUs? I'm just asking you, would you consider.

[Shannon Sharp]

Oh, you asking me for real?

[Cheryl Underwood]

Yeah, I'm asking you for real. Would you consider it? Sure. Would you consider it? Because what I.

[Shannon Sharp]

How far are we going out on the cruise?

[Cheryl Underwood]

I think I know. I. I don't know. Let me find the answer.

[Shannon Sharp]

Can I be on Zoom while y'all on the cruise?

[Cheryl Underwood]

Why? You scared of water?

[Shannon Sharp]

Yeah. Yeah.

[Cheryl Underwood]

Well, I could tell your ash ass bit into water. He never had that one, didn't he? Never had that one. You been in? Somebody wanted you?

[Shannon Sharp]

Yeah, I'm scared of Watershed.

[Cheryl Underwood]

You scared of being on the boat?

[Shannon Sharp]

Yep.

[Cheryl Underwood]

Well, why don't you get on the. Why don't you get on the first part in New Orleans and do it from there and Then you can go home.

[Shannon Sharp]

Okay.

[Cheryl Underwood]

Okay. Well, I'll tell you what. I'll find the cities. Let's see if we can make it work. But I will tell you this, Tom Joyner, being a radio man, and I wanted to do radio, but they don't. I don't see them. The only girl that I see doing it, I think Cafe Mocha is doing. There's some other sisters that are doing radio, but I don't see them leading their own show in a way that you see the guys. Adidi McGuire's the only one that I see doing it, and I'm so proud of her. But I wanna do What Ricky and D.L.

[Shannon Sharp]

Oh, okay. Yeah, yeah.

[Cheryl Underwood]

I wanna lead a show. But on the other hand, Steve Harvey gave me those opportunities. All that footage from the Hoodie Awards, I was gonna get Pastor Sapp. I thought I'd be a great first lady. I give up, Dr. Drinking, cussing. @ least in your presence, brother. You know? But I wanted to do those different things. But what you see is the opportunity that people really respect. And it was Steve Harvey. When I thought somebody was playing on my phone, and I did not believe that it was CBS calling me for an interview for the job.

[Shannon Sharp]

You thought you was getting pranked by Kevin Hart, Steve James.

[Cheryl Underwood]

I called they asses, every number I had, and stop playing on my phone. Steve was like, you might want to call him back. It might be cbs. And he was right. And he was right. So I never want us to be pitted against each other, but I do want us to help each other. We should be doing cooking shows. We should be doing sports panels. We should be doing everything because we're funny and we're smart and we can do it all.

[Shannon Sharp]

Beauty Shop. It was Queen Latifah, Adele Givens, Laura Hayes, Sherri Shepherd.

[Cheryl Underwood]

Yes.

[Shannon Sharp]

Cause Laura Hayes, wasn't she on Comic View? Yes, that was.

[Cheryl Underwood]

Yes. Ms. Laurie.

[Shannon Sharp]

Ms. Laura.

[Cheryl Underwood]

Yes. And Toe Up Def Comedy. Yeah.

[Shannon Sharp]

Kahmora Lee Simmons, Omar Hedrick, Lisa Ray, Octavia Spencer, Birdman. How was that experience?

[Cheryl Underwood]

It was a great experience to watch, great producing, you know, to watch Queen Latifah pull that together with her team and to watch us as an ensemble. Alicia Silverstone, the girl Clueless.

[Shannon Sharp]

Yes.

[DraftKings Announcer]

Yes.

[Cheryl Underwood]

That girl was funny as. I don't know what. It was a really good experience. In one of my first movies between Beauty Shop, I got the hookup. Two can play that game. Vivica Fox gave me a lot of jobs, too. And I really loved being in Beauty Shop because they let me ad lib. But Also could understand the parameters of the script. What I tried to do, the one thing that I was taught was do what's written on the page first and then act. Can I show you something? And then stay within the parameters of the script. Because if you add lives so far away, then the other actors can't say they lying or do what they want to do. That's why I want to produce. I want to produce. I have gospel play scripts. I have people that I pay. I'll write the idea, they'll write the scripts. Because I want to put people to work. We can do it like Tyler is doing it. You know, Tyler got the studio. Come on, let's all work together and help each other. There's enough money out there for all of us. So that's what Beauty shop really poured into me.

[Shannon Sharp]

Why don't we work together more?

[Cheryl Underwood]

Because you wanna say it in front of.

[Shannon Sharp]

That's your camera.

[Cheryl Underwood]

You wanna say it in front of the people. Cause he won't. If he would just give me something. If he would just give me a taste, a little taste, I would come to work early. No, I'm just kidding. Why don't you and I work together?

[Shannon Sharp]

No, why don't we work.

[Cheryl Underwood]

Oh, nigga, I thought. Sorry. I thought you. Why we. Like. Me and you don't work together. We can't work together. Cause whatever in your life gonna be mad. Why is she here, Ike? That's what's gonna happen. That's what's gonna happen. I think that. I think we have the money. We have the pull and the influence. Back when they were making what they call black exploitation. Fail, sweep back. Come on, man. Bad as much. The Mac was really about some brothers up in Oakland running a club called Sweet Jimmies. We can do that again, Superfly. We can do that again and have a soundtrack. And it doesn't take a lot of money. One thing I would ask everybody to do. Don't come in and try to make the money. Make up the money that you haven't gotten. You're gonna price us out, right? We have to understand, as a business, do the movie and take the percentage, right? Promote the movie. We can make a movie in six weeks. But we, if we come together, the writers, the producers, the hairstylists, everything, we can fry the chicken for the craft service, do what we need to do. And if we do that and our movies are making money, they will invest in us again because it's about commerce. And I think we can change that narrative. And I know you can, because you took A little club. Shay Shay. And I'm calling it a little show because it wasn't as big as it was. And then here comes Katt Williams. I remember Katt when he was Cat in the Hat. And let me tell you a little Cat Williams story while we talking. I remember Cat when he was Cat in the Hat, doing the jokes about the short dude in the car and all that stuff. We knew he was funny then. And I had got the host job for Comic View and Cat Williams performed. I think it was me, Cat and Michael Carr, and I think Mike Washington was on that show. We have the comedy connection. I think it was in Greenbelt, Maryland, if I'm not mistaken. I stand corrected. I watched Katt Williams do a set. I called Stephen Hill. I said, get here as fast as you can. I have watched something great.

[Shannon Sharp]

Wow.

[Cheryl Underwood]

They said, what is it? Katt Williams is destroying a room and I cannot follow him now. I got cursed. I did what I needed to do that night, but what I saw was something special. I said, and so Stephen gets there and he's looking at. He's dying, laughing. I said, I need that guy on my season of Comic View. And he was like, well, why would you do that? I said, because he's going to be big and he's special and this is his shot. And everything propelled. He was already doing great stuff, but everything propelled. I just want us to, if we disrespect, disagree in private.

[Shannon Sharp]

Yes.

[Cheryl Underwood]

You know what I'm saying? And you can tell your version of the story. I'm telling my versions of the stories. But you notice that I'm editing myself because I'm not going to do it at the expense of someone's self esteem. I'm not saying Kat did that. I'm just saying I knew Katt Williams was gonna be special because I saw it in him and I was willing to step back. You gotta know when you can't follow something, you gotta know it. That's why I host now.

[Cheap Caribbean Announcer]

Mm.

[Shannon Sharp]

I got the hookup. And I got the hookup, too. Master P. You mentioned John Witherspoon.

[Cheryl Underwood]

I love Master P. I love Master P. Great businessman, very, very smart. Always gave me an opportunity. You know who else gave me an opportunity?

[Shannon Sharp]

Who did?

[Cheryl Underwood]

Uncle Luke.

[Shannon Sharp]

Really?

[Cheryl Underwood]

Yes. When I was first doing really, really raw, raw materials. Not like my stuff ain't raw now, but this is where I was polishing.

[Shannon Sharp]

Really uncut.

[Cheryl Underwood]

Yeah, yeah. And. And he said, cheryl, I want you to, you know, record some material for us and put it out there. And you notice something Odd. In all the stuff that's going on with the sexuality, you know, and gaffling people and everything. Who name is not in it. Uncle Luke. He started it, but he didn't do it. He didn't cross that line. He didn't cross that line. It may have been a party atmosphere.

[Shannon Sharp]

Yes.

[Cheryl Underwood]

But he didn't do things power corruption and we have got to start protecting each other and don't do that shit. When you football player, did they still give you a handler, A person that kept you out of trouble when you first got in the league?

[Shannon Sharp]

No, no, I mean, you know, they. We used to have these videos where they say, well, you know, obviously you can't gamble and be careful who you associate with.

[Cheryl Underwood]

Absolutely.

[Shannon Sharp]

But I was very, very fortunate that I had an older brother that was in the league that could guide me.

[Cheryl Underwood]

Sterling.

[Shannon Sharp]

Yes. That could guide me and let me know. Okay, bro. This is how you need to do it. This is what you need to. Everybody doesn't handle that. But at the end of the day, you know, Cheryl, you know, grown men is gonna do what grown men do. Because it's kinda like you have a financial advisor and he might say, Cheryl, you don't need to do this. Well, it's Cheryl's money and Cheryl takes the money and do. All he can do is advise advice on counsel.

[Cheryl Underwood]

But why do you have him if you don't take advice on counsel? I'm shout out my business manager, Larry Turner. I like to thank you. I thought he was black. Cause he had his whole name on his card. It was long. Who is J. Turner? I said, these brothers is doing the thing. They attorneys, they financial planners. I walk in this little Jewish dude, I was like, well, what's up? Grow my. If you can show me that you know what you talking about. I have a saying. Don't wake up in the middle of surgery talking to the surgeon. Let people do what they gonna do. If you gonna take advice and counsel. Take advice and counsel.

[Shannon Sharp]

Exactly.

[Cheryl Underwood]

But sometimes you get so much money and power that you start to do things and people are afraid to tell you. Don't do that, you know. And don't record the what is with the recording of the documentation of. And I'm going to tell you this. I grew up in Chicago, I was running these streets. We knew R. Kelly and it's a lot of stuff that we know about people. But how do we save someone from themselves? And how do we teach? With great fame comes great responsibility. Right? And money and power. And if you treat it right, God will give you more. You don't have to do this wild stuff that you're doing and you don't have to take it out on people. People say, well, money changed people. No, money makes you more of what you already are. There it is right there.

[Shannon Sharp]

I mean, you are who you are.

[Cheryl Underwood]

Absolutely. Absolutely. I walked up on, I bucked up on a lot of dudes and they be like, nah, Cheryl, you a good girl. I'm like, I'm glad you think that. Right. I'm gonna circle this bar one more time. And if you still here when I come back, son and poppin'right Let me buy you this drink. Let's go. Right, but like you said, you have choice. But there's got to be somebody there, especially these young boys. It could destroy their life.

[Shannon Sharp]

Yes.

[Cheryl Underwood]

That's why I have a sports initiative. Young boys, young as three years old, learning different sports but also getting an education. But we need you men to come back into these boys lives so they will understand you have somebody to talk to. You have big brothers out there. And don't put everything on social media. All you street soldiers out there holding all the money up the ice IRS is watching and they waiting on you. And if you had a PPP loan and now you in jail, but ain't nobody else in jail. Come on man, we can do this better, right? What else you want to ask?

[Shannon Sharp]

This concludes the first half of my conversation. Part two is also posted and you can access it to whichever podcast platform you just listened to part one on. Just simply go back to Club Shay Shay profile and I'll see you there.

[DraftKings Announcer]

When it's tip off time at my house, there are a few things that are must haves on my checklist. My fellow friends and fans. Check my favorite jersey. It is good luck. Check an iconic drink that's a fan favorite.

[Cheryl Underwood]

Check.

[DraftKings Announcer]

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[Cheryl Underwood]

We're the hosts of Mind the Business Small Business Success Stories produced by Ruby Studio and Intuit quickbook. Catch up on seasons one and two and join us for a brand new season of the podcast as we talk to small business owners about how they manage and grow their businesses with the help of platforms like Intuit QuickBooks.

[DraftKings Announcer]

Listen to mind the Business Small Business Success Stories on the iHeartRadio app, Apple Podcasts or wherever you get your podcasts.