INTERVIEW: Sheryl Underwood Talks Black Female Comedy, Sharon Osborne, 'The Talk,' Gayle, Druski + More

Summary

Podcast Summary: The Breakfast Club – INTERVIEW: Sheryl Underwood Talks Black Female Comedy, Sharon Osborne, 'The Talk,' Gayle, Druski + More

Podcast Information:

• Title: The Breakfast Club
• Host/Author: iHeartPodcasts
• Description: The World's Most Dangerous Morning Show, The Breakfast Club, With DJ Envy, Jess Hilarious, And Charlamagne Tha God!
• Episode: INTERVIEW: Sheryl Underwood Talks Black Female Comedy, Sharon Osborne, 'The Talk,' Gayle, Druski + More
• Release Date: April 16, 2025

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Introduction

The episode begins with cheerful promotional segments from Coca-Cola and State Farm, setting an upbeat tone for the morning show.

[00:00 – 00:32] Coca-Cola & State Farm Advertisements

• Coca-Cola: Highlights the joy of sharing moments with friends through limited edition "Share a Coke" bottles.
• State Farm: Emphasizes empowerment in career building with support akin to a good neighbor.

Guest Introduction

[00:32 – 00:40] Introducing Cheryl Underwood

• Hosts: DJ Envy, Jess Hilarious, and Charlamagne Tha God enthusiastically welcome Cheryl Underwood as the special guest.
• Jess Hilarious: Sets a playful tone, hinting at the depth of conversation to follow.

Black Female Comedy: Hidden or Struggling?

[00:40 – 02:22] The Struggle for Visibility in Comedy

• Jess Hilarious: Raises the question of whether black female comedians are hidden or need to struggle for recognition.
  • "Black female comedians. Are we hidden or do we gotta struggle for it?" [01:03]
• Cheryl Underwood: Responds confidently, asserting that struggle isn't necessary.
  • "We ain't gotta struggle for it." [01:03]
• Jess Hilarious: Challenges Cheryl's statement by pointing out the lack of radio shows, sitcoms, podcasts, and movies featuring black female comedians.
  • "Why we ain't got no radio shows that we do ourselves, sitcoms that we do ourselves, podcasts that we do ourselves, and movies that we do ourselves." [01:04]

Evolving Platforms for Black Female Comedians

[02:22 – 04:28] Transitioning to Personal Platforms

• Charlamagne Tha God: Suggests that radio's declining appeal to younger generations has impacted opportunities.
  • "Radio didn't look sexy to a generation, so there wasn't a lot of people who went and pursued it." [01:44]
• Cheryl Underwood: Discusses her podcast's evolution from general topics to providing advice and fixing personal issues.
  • "We wanna hear something different. We can go online if you wanna hear what you talk about online." [04:28]
• Jess Hilarious: Expresses a desire to create her own content, including podcasts and books, to share her experiences and insights.
  • "I need to write a book. I need... I need arm on some ties or something." [02:22]

Challenges in the Entertainment Industry

[04:28 – 16:21] Navigating Industry Hurdles

• Jess Hilarious: Highlights the financial and promotional challenges faced by black female comedians. Emphasizes the need for collective efforts to produce movies, series, and other content.
  • "We need to start making these movies. We need to start getting together, making these series." [03:10]
• Cheryl Underwood: Agrees on the importance of leveraging platforms to reach broader audiences and effectively promote their work.
  • "My platform is big enough and I do have... the Breakfast Club, where I Can push, take my tickets, my reaches even further." [16:11]

Political and Social Commentary

[16:21 – 22:47] Engaging in Community Empowerment

• Jess Hilarious: Delves into the importance of community involvement in political and social spheres, advocating for support within the black community to influence change.
  • "Every civil rights organization, every Greek letter organization, everybody get back into the community. If you are not touching the community, we will not win this." [19:39]
• Cheryl Underwood: Emphasizes the necessity of bridging traditional platforms with modern media to maintain influence and drive progress.
  • "I got the fan base here and my older folk more established. And then I got the fan base on social media." [17:39]
• Hosts Discussions: The conversation touches upon the challenges black communities face in media representation and political engagement, highlighting the need for proactive involvement to sustain influence.

Personal Anecdotes and Humor

[22:47 – 37:38] Balancing Serious Topics with Levity

• Jess Hilarious: Shares humorous and personal stories, including an anecdote about a kiss with Flavor Flav, showcasing her charismatic and comedic personality.
  • "This dude was getting drinks, everything. So I was like, okay, it's time for me to go." [54:57]
• Cheryl Underwood & Hosts: Engage in playful banter, maintaining a light-hearted atmosphere while discussing serious topics. This segment blends personal experiences with humor, making the conversation relatable and entertaining.

Promoting Community and Future Projects

[37:38 – 57:24] Building the Future for Black Female Comedians

• Jess Hilarious: Advocates for the creation of reality shows and movies featuring female comedians, stressing the importance of financing and producing their own content.
  • "Why are we not doing reality shows with female comedians in it?" [39:56]
• Cheryl Underwood: Encourages collective action and leveraging existing platforms to produce and promote new content.
  • "We can do that. We can do this." [39:57]
• Call to Action: Hosts and Cheryl emphasize the necessity for the community to support one another through attendance at events, purchasing tickets, and sharing content to sustain and grow their presence in the industry.
  • "We got to start talking politics too. Let's do it." [57:05]

Closing Remarks and Final Promotions

[57:24 – End] Concluding with Promotions and Final Thoughts

• Jess Hilarious: Wraps up the discussion by reiterating the importance of community support and promoting upcoming performances.
  • "I'm gonna get to work Monday because that's what I want." [39:45]
• Hosts and Cheryl: Continue light-hearted interactions, encouraging listeners to attend shows and support black female comedians.
• Final Advertisements: The episode concludes with wrap-up promotions from Coca-Cola and State Farm, reinforcing the show's connection with its audience.

Notable Quotes with Timestamps

• Jess Hilarious: "Black female comedians. Are we hidden or do we gotta struggle for it?" [01:03]
• Cheryl Underwood: "We ain't gotta struggle for it." [01:03]
• Jess Hilarious: "Why we ain't got no radio shows that we do ourselves, sitcoms that we do ourselves, podcasts that we do ourselves, and movies that we do ourselves." [01:04]
• Charlamagne Tha God: "Radio didn't look sexy to a generation, so there wasn't a lot of people who went and pursued it." [01:44]
• Cheryl Underwood: "We wanna hear something different. We can go online if you wanna hear what you talk about online." [04:28]
• Jess Hilarious: "I need to write a book. I need... I need arm on some ties or something." [02:22]
• Jess Hilarious: "We need to start making these movies. We need to start getting together, making these series." [03:10]
• Cheryl Underwood: "My platform is big enough and I do have... the Breakfast Club, where I Can push, take my tickets, my reaches even further." [16:11]
• Jess Hilarious: "Every civil rights organization, every Greek letter organization, everybody get back into the community. If you are not touching the community, we will not win this." [19:39]
• Jess Hilarious: "Why are we not doing reality shows with female comedians in it?" [39:56]
• Jess Hilarious: "I'm gonna get to work Monday because that's what I want." [39:45]

Conclusion

This episode of The Breakfast Club delves deep into the landscape of black female comedy, exploring the challenges and opportunities within the industry. Through engaging discussions, personal anecdotes, and humorous exchanges, Cheryl Underwood, along with hosts DJ Envy, Jess Hilarious, and Charlamagne Tha God, shed light on the necessity for black female comedians to build and maintain their own platforms. The conversation emphasizes community empowerment, authentic representation, and the collective effort required to sustain and grow their presence in media and entertainment. Listeners are encouraged to support upcoming events and initiatives aimed at fostering a thriving environment for black female talent.

Transcript

[Coca-Cola]

The best moments happen when you're with your people, laughing, vibing, just enjoying life. Coke is making those moments even sweeter. Share a Coke is back and it's all about sharing with the whole crew. Doesn't matter if it's your bestie or bro. There's a can with their name on it. So grab one for the squad and make some memories. But hurry, because these Coca Cola limited edition bottles and cans won't be here forever. Don't miss your chance to share a Coke with all your favorite people.

[Carlos Miller]

Wake that ass up early in the morning.

[Jess Hilarious]

The Breakfast Club.

[DJ Envy]

Morning, everybody. It's DJ Envy.

[Jess Hilarious]

Just hilarious.

[DJ Envy]

Charlamagne, the guy. We are the Breakfast Club. We got a special guest in the building.

[Charlamagne Tha God]

Yes, indeed.

[DJ Envy]

Cheryl Underwood, ladies and gentlemen.

[Jess Hilarious]

Baby, listen. Okay, how. Where we starting? Wherever you want, Ms. Underwood. Ask me anything. Well, listen. Cause I got to, you know, because I'm old school, I gotta sell these tickets, mix and mingle, you know, we out there street walking. These tickets. Absolutely. I need Joe. Cause what is that? I gotta ask y'all a question. Black female. Female comedians. Are we hidden or do we gotta struggle for it Now, Jess, what's. What you thinking?

[Cheryl Underwood]

We ain't gotta struggle for it.

[Jess Hilarious]

Well, then why we ain't got no radio shows that we do ourselves, sitcoms that we do ourselves, podcasts that we do ourselves, and movies that we do ourselves. Back in the old days, you know, simply marvelous. Everybody was doing. Lord. Hey, everybody. It seemed like now something has taken the place of what we used to get. It used to be we was the Marlowe Gill. We walk in, throw that joke up, hit Sherman Hemsley and walk out. Now we don't even get fat, right?

[Charlamagne Tha God]

I got a. I got a reason. I think because I saw you on Club Shay talking about the radio portion. I think for whatever reason, radio didn't look sexy to a generation, so there wasn't a lot of people who went and pursued it. So, you know, you got your Deedy Maguires, but D been around. D been around since.

[Jess Hilarious]

She's a radio person.

[Charlamagne Tha God]

That's right.

[Jess Hilarious]

Right.

[Charlamagne Tha God]

That's right.

[Jess Hilarious]

But. But if D.L. okay, D.L. steve, Ricky, then why is it not me just not saying we don't want to work here? Because I've been trying to get a job here. Let me talk to y'all about y'all. I've been trying to get a job here. You know, I keep coming up here and y'all keep moving. The me think I got the running from you. Listen, like. Like, we used to be the girl okay. They start packing us up. Listen. Cause I been trying to get a job. When you got a job, I was like, oh, maybe I should lose a couple of pounds or something. Put some nails on or something. I had to take my nails off cause they was killing me. Oh, and fungus ain't for punks. Okay, listen, that's your ring alone.

[DJ Envy]

You better check to make sure nobody at your front door.

[Jess Hilarious]

No, listen. Okay, I know what that means. They don't quit walking across my stuff because that's what make the battery run out. Go to bed. And then they ain' even us, you know, if it was us, you could be all night long. But when it's other races of people, take your ass to bed and stop messing my battery up. Okay, what was I talking about?

[DJ Envy]

You were talking about people doing radio.

[Charlamagne Tha God]

Women. Yeah, women not being in the position.

[Jess Hilarious]

I want to do radio. You know, I call Doc all the time. Doc, Doc look out for me. I'm not on CBS no more. We gotta keep working. I would. I would do a podcast. What would I want to talk about? Well, I know what I want to talk about. What would you recommend? Because you know, you be making that money too. You be. Man, listen, I need to write a book. I need. Matter of fact, I need to just do the Charlemagne, the God success story. Okay, so wait a minute now, hold on. What we gonna talk about? Because, you know, and then this the.

[Cheryl Underwood]

Thing it is when you do a podcast, you gotta really think about what is it that people wanna hear from Cheryl?

[Jess Hilarious]

What you think, Jess?

[Cheryl Underwood]

You know what I'm saying?

[Jess Hilarious]

What you think when you see me.

[Cheryl Underwood]

Like, soon as you came in here, you looked at me and was like.

[Jess Hilarious]

What'S going on over the place? With a joke, girl. It was a. When I woke up, no, you looking fly to death. That's how you come to work in the morning. You come to work, but ready to, you know, if I need to in the. Meet me in the break room. Listen, don't sleep on that money. Right? Then the Breakfast Club. Don't let the success fool you. We will squad with any radio show. Come up here with this smoke, you gonna get smoked back. We the Breadfit Club. That's right. Cause we gonna hit you in the morning.

[Charlamagne Tha God]

That is a good question. You asked when Jess first started her podcast. Carefully reckless. She was talking about pop culture and stuff. And then it turned into you talking.

[Cheryl Underwood]

About yourself and then just fixed my mess.

[Charlamagne Tha God]

Yeah.

[Cheryl Underwood]

Cause what I went into it with thinking, all right, Just like, all right, I'm gonna talk about What I wanna talk about. But no podcast. They don't really see you. We got a lot of people that shoot their podcast, but I was just doing audio, you know what I'm saying? Cause I'm already video visually everywhere else. So I'm like, no, I'm gonna just lead us to audio. But the mistake I made was like, all right, they wanna hear what they hear online. Nah, we wanna hear something different. We can go online if you wanna hear what you talk about online.

[Jess Hilarious]

That's right.

[Cheryl Underwood]

Give us advice on stuff. Jess, your storytelling is amazing. All of your experiences, you always been an open book, Jess. So we going through the same things. How did you get through it? How can you help us get through it? That's when it changed from me being just with the mess on my podcast to me just fix my mess now. You know, people call up, I can fix people's mess here. Every Thursday, you know, they call up, they having situations at work, they having, you know, turmoil in their relationship with friendships, family, stuff like that.

[Jess Hilarious]

Well, since you fixing things, I need you to find me a man. And this where we going? You go to every Red Lobster in the history of mankind. Because it's a brother that run Red Lobster. Really? Okay, so what's up with him? What's up with him?

[Cheryl Underwood]

His contact and he asked, how old is he now?

[DJ Envy]

Single, I believe he young.

[Jess Hilarious]

He's young.

[DJ Envy]

He's in his 30s. I think he in his 30s.

[Jess Hilarious]

I do that. Y'all saw me at club say I go 35, 95. What you trying to do? 35, 95. 35, 95.

[Charlamagne Tha God]

You ain't never had sex with no 95 year old.

[Jess Hilarious]

Listen to a 95 year old man. I'm a young tenderoni to a 95 year old. To Rufus. Rufus. Rufus and Cheryl. Nathaniel Levinican, Malachi. I'm younger him, but to a 35 year old man. I could teach him things. Plus, I need my privacy, you know, I want somebody to live right next door or in another state. You know, just call me at night, check on me, see if I'm still alive.

[DJ Envy]

Oh, you don't want to live with nobody?

[Jess Hilarious]

No, I don't think that's a good idea in the beginning. Well, I don't believe in shacking. I never believed in that. I'm not living no man. Because you don't know the day of the hour, the master return, you know, but. And. And I don't like. I don't like sex. What do you mean?

[Charlamagne Tha God]

You think the man just gonna die? You don't want to be with him.

[Jess Hilarious]

No, but you just don't know when Jesus coming back. Oh, so now, right? I'm living with a dude and I think the Lord be looking down in my life, you know, be like, man, I was just about to give her all these blessings, you know what I'm saying? To give her all this money and everything. She ain't she sleeping on this premarital sex. No, that's when I get caught slipping. Now, listen, sometimes I get caught, I get caught slipping. You know, fair exchange ain't no robbery. If you take me out to eat, I need to do something for it, you know what I'm saying? I need, I need arm on some ties or something, you know, Cuz a lot of women. Yeah, I did what I did. Shut up. You need to do something for this, man. He done took you out, you done ate well and everything. He don't just like you and you up there. Kiki, Kiki, Kik. No.

[Charlamagne Tha God]

So you trick a little bit?

[Jess Hilarious]

Cheryl. No, I wouldn't say I trick a little bit. I just say fair exchange ain't no robbery, you know what I'm saying? I'mma talk to you and I'mma tell you what I can do, what I can't do. I'm telling you, if you, if you want something that I don't know how to do, I call Jeff. Jess, you want to jump in this?

[Cheryl Underwood]

Do I want to do things?

[Jess Hilarious]

Yeah. Tagged in because the things I can't do, I'm over here making sandwiches.

[Cheryl Underwood]

You know, I'm engaged, so I can't.

[Jess Hilarious]

I would have done that. Listen, okay, how did you get engaged? See, I need to do your joint so you can tell me. How did you get engaged? Because I tell her just how did you get engaged? She got a Mexican.

[Charlamagne Tha God]

He needed paper.

[Jess Hilarious]

Listen.

[Charlamagne Tha God]

Wow.

[Jess Hilarious]

Wow. Yes, he is Mexican and black. But he's black first. Okay, but. But you said Mexican first, so you know what that means.

[Cheryl Underwood]

She said Mexican first.

[Jess Hilarious]

You say she? Yes, yes. You say she.

[Cheryl Underwood]

She said Mexican.

[Jess Hilarious]

Are you what? Yes.

[Cheryl Underwood]

Casherl that's his wife sitting right next to him.

[Charlamagne Tha God]

Identify as what I need to identify as in the morning.

[Jess Hilarious]

Oh, you in the pronouns.

[Cheryl Underwood]

Yes, yes.

[Jess Hilarious]

See, that's how we lost. You can't be in everything.

[Charlamagne Tha God]

Black people give a damn about your pronoun. Don't listen to her.

[Jess Hilarious]

Black people are not doing all of that. We get frustrated. That's when we call you straight your name. We not against your rights and everything. But we can't be thinking about all this stuff and Everything. Because people gotta stop walking on the backs of our movement. Then go to get they thing and then they pulling it from everybody. See, that's what I want to talk about. I got questions. I want to ask questions, but also I want to do relationship. I want. When you get called in something. Me and Shannon used to kick it. You know, we used to kick it. I was trying, man, I was trying to get it.

[Cheryl Underwood]

Shay, they used to call him Shay Shay back then.

[Jess Hilarious]

No, I didn't know who that was. When I heard Shay Shay, I was like, bruh, you know, Because I was trying to. Yeah, I was trying to put that forearm that went back. Just take it, take it, take it. You can take it, take it. Go to sleep, go to sleep, go to sleep, go to sleep, go to sleep, go to sleep.

[Cheryl Underwood]

So back when, when y'all used to say, okay, so when you saw that live or whatever, right, You.

[Jess Hilarious]

That took you down in all kind of sports. Baseball, soccer, Olympics, football, hockey. I was running up in all kind of sports. Because I'm the different girl. I'm the girl that a dude get with and go, you know, I never thought I would, like, shad up. Shut it up. Take it, take it. Go to sleep, go to sleep, Go to sleep. So you got. You got the. The Mexicans and black. You mixing black together. Cuz I mess with that, too. Gateway to legal immigration right through here. I mess with all of that Colombian, Cuban, Mexican, El Salvadoria, you know, El Salvadorian is really black, you know, Cuz they be. You know, they be trying to say who ain't coming. And now he done picked up everybody. But you voted. You voted. You singing, you voted.

[Charlamagne Tha God]

But you didn't think he was gonna.

[Jess Hilarious]

Flip the script on you. Anybody hustle hard, like Donald hustling hard and did what he did.

[Charlamagne Tha God]

But we knew it.

[Jess Hilarious]

We knew it. So I would want to talk about everything that's right. And I love the Lord, and I think the Lord know my heart. That why I'm. I'm back on tour, cuz I got to make this money, cuz I want to finance everything that I want to finance. And I want somebody to jump in and help elevate my stuff. Like, I got an animated vehicle, you know, but it's. I wanted to be profane. I like profane language. I like profane topics. I like. Like, I saw you on the Daily Show. I thought your commentary is very good. And I think that with all of us working and all of us making this money and opening doors for all of us, then we need to get together and start making these movies. We need to start getting together, making these series, and then we need to work together. So if you know how to write a book, you do a 20 book deal over at your publishing company and you find 20 of us that got a story to tell. Because I got a story to tell. I'm just not gonna. Until somebody pay me. Yeah. To tell it. Because I got that day that somebody came out of the bag of me when I found out that I thought my friend was my friend, but I found my friend was my co worker. You want the inside of that story, you gonna have to pay me for it. And I tell you. I tell you everything. You know what I'm saying? Money talking, walk.

[Charlamagne Tha God]

Hey, you look good, too, Cheryl.

[Jess Hilarious]

You lost what, about 110? I was like 250. I was wilding. I would watch when she was 250. But remember, we had a table. We had. Because we had a table. And you know, they. I was coming out last, and I was. I was waddling to the table. Right. You know what I'm saying? I was cross between Biggie and Tracy Morgan. Right. So. So. No, for real, for real. Wait a minute. Wait, was I here?

[Charlamagne Tha God]

Was.

[Jess Hilarious]

Was y'all to show that. That I said I look like Lil Yachty and Lil Yachty.

[Cheryl Underwood]

No, see, I thought it, but I never said it.

[Jess Hilarious]

I said, you pointed at her. I thought I said it. I said cuz. I said, cuz I saw the pictures. No, because remember, Lil Yachty did video.

[Cheryl Underwood]

Yes.

[Jess Hilarious]

And I said, oh, and then there's a picture, and somebody put them side by side, and I. I took it. I claim it. If you got a good line on me, I'll take that line. But if it ain't a good line, you might get tapped. You know, you might get tapped these little bitty. These little sharp knuckles and that. I lost 110 pounds. I got a good black doctor, too. Dr. Zuri Morrell. You got to check him out. He's the brother that sometimes you need somebody in your own culture that can tell you understand? Because somebody talk to you and because they got a white coat on, you be like, okay, I'm gonna do it. I'm. You find out. Don't do that. So having Dr. Zuri Morrell, no diabetes, no high blood pressure, you know, moving around. But here's what we need. We need to be talking to these pharmaceutical companies. It cannot be so expensive to live healthy. And that's where the problem is. And that's where we need to use the media and we got to get people.

[Charlamagne Tha God]

The pharmaceutical companies should be calling out the food corporations, because the food corporations are making all this food that's getting them sick. Then we got to go to the pharmaceutical companies and get health insurance that we can't afford and medicine that we can't afford.

[Jess Hilarious]

And then you put they working hand in hand, right? But then you put dude in there. Listen, I'm not against RFK Jr. I know the dude. I met him and everything. I met his wife and everything. But when you putting a dude in there going, well, vaccines do this and do this. But, you know, now that the measles is coming back, you might want to get it. Okay, who are we listening to? I need a dude that sound like he know what he talking about, because I can go to a dude on the corner if I want to get possibilities. That's how we live. If somebody say, you got fibroids, okay, drink corn water. Okay, we already live in that, but you can't be in charge of nothing. Talking about drinking corn water. But big ups to him. Talking about putting what's the beef tallow back in the french fries.

[Charlamagne Tha God]

He did it already. I think it's Shake Shack or one of them.

[Jess Hilarious]

Yeah, and I heard Popeyes too. But listen, I'm not against it. You just can't eat it every day. You know what I'm saying?

[Charlamagne Tha God]

So you had surgery to lose the weight?

[Jess Hilarious]

No, no, I was going to have it because that is what was recommended. And then when I went to get the. I did the psychological test, because you got to go through a lot of testing before you get the surgery. And then I went to get the. I was getting my colonoscopy. So I said, well, you might as well do the endoscopy because the equipment goes down your throat like, okay, nevermind. I'm about to go on a whole nother tangent. But when I went to do that, my colorectal doctor, Dr. Zori Morrell, brother over at Cedar Sinai Morehouse man, said, why are you doing this? And so he started to read my record, and he said, try this first. So then he put me on Saxenda first, and then I went to wegovy and everything changed. And we monitor all of my vitals and my blood work and everything, and that's what you gotta do. But this can be done. The other thing that can be done, we need to be buying up property that people don't want and changing neighborhoods and putting healthy stuff next to stuff we love. And then we need to put small clinics in every neighborhood. You don't have to go to the hospital far away just to come down and get your blood pressure checked. You need to be able to walk. In the old days, we used to walk places. We need to bring that back. We who have money, access and power need to use that money, access and power. Because now they'll give us something, somebody else will start using it, and then they'll take it away. That's right. You ain't hurting me. Hustle hard.

[DJ Envy]

It's funny that you said that. You know, we were talking earlier that we try that, but all the vegan spots have been closing. People haven't been going to the vegan spots. They haven't been going to the healthy spots no more. So all the healthy spots have been closing.

[Charlamagne Tha God]

But I don't know if the healthy spots is in the hood, though.

[Jess Hilarious]

And I would say this. It's not to everybody don't like to hear I'm gonna be a vegan, because then it sounds like, what I don't get to eat. Like, I live for a good fried pork chop, but I can't metabolize it every day like I to when I was younger. So when you say being vegan, that's eating an apple, that's eating fruit, that's. That's getting your natural fiber. Right. But once you hook me on something processed and my body now wants that, I think there's. It's okay to have everything that's out here. That's right. That's. That's right. But if we don't walk around, if we ride everywhere. I live in California. We ride everywhere. Where do we use this? We don't want to just use this to entertain. We want to enlighten, empowerment and elevate, and that's what we need to be doing. So if I was to ever do a podcast or type of show, I would want to be able to talk to everybody, and I want to move product. You know why? Integration is the key. You want to stay on the air, you must be making the corporation money from everybody. And that's what I want us to be about. So we will have the money. I'm working with a team of promoters to make sure my tickets sell. Why? Because the clubs and some places don't promote. Yeah, they think you're supposed to do it on social media. Yep. What do you think about that, actually?

[Cheryl Underwood]

Well, it's an upside and a downside to it. Thank God I am. My platform is big enough and I do have, you know, now, you know, the Breakfast Club, where I Can push, take my tickets, my reaches even further.

[Jess Hilarious]

Yes.

[Cheryl Underwood]

And thank God for my platform that I can sell my tickets right on my own with a couple posts. Cause if not, damn. Like how you booking me? But you don't wanna promote me.

[Jess Hilarious]

That's right. You put me there. You want me to do your job, right? Then are you gonna compensate me for that? When Kevin Hart had his promotion game, his social media game before he was that Kevin, this Kevin Hart, he was that Kevin Hart. And then those emails came out that they wanted to access it, but they didn't wanna compensate him for what he built.

[Charlamagne Tha God]

He used to put that newsletter out. He used to have his man walk around the comedy club, Wayne and get everybody's email and he would send a newsletter out.

[Jess Hilarious]

That's right. And we gott. But my feeling is everybody audience is not a social media audience. My audience, old school, they don't believe that Jesus is coming back until they hear the Breakfast Club say where Jesus is going to be.

[Charlamagne Tha God]

They on Facebook though.

[Jess Hilarious]

Facebook, Sorta.

[Cheryl Underwood]

But you know what? They were on Facebook. But everything. With everything updating, it's hard to keep up with how some of that stuff works now. So. No. And that's when I realized when I got this job, I'm like, well, that's a total different.

[Jess Hilarious]

Yeah.

[Cheryl Underwood]

Because I'm starting to see more and more and more older, more established people in their careers coming to the show. And when I got. When I'm on stage and I'm talking about what's going on on social media, it's funny, but I can tell that they don't.

[Jess Hilarious]

They don't. They don't make that new lab. Okay, cool.

[Cheryl Underwood]

But that's the difference. I got the fan base here and my older folk more established. And then I got the fan base on social media.

[Jess Hilarious]

And when you merge them together now you have power. And for me, this is still in my car. This is still in my house. Everybody pronounced the death of terrestrial radio and it's still alive. And it's going to stay alive. That's right. So we have to be involved in it and we need to talk to politicians. Democrats want to take it back in the midterm. Then you got to put that money on radio, and especially black radio. Why? Because the Republicans did just enough to get our attention. Now everybody talking about all the black men that voted Republican. No, that's not true. She still got a large amount of the black male vote. What they did was they got enough for the distraction, hustle to work. And we have to tell people Advertisers have to advertise on this show. Why? If it don't make money, it don't make sense.

[Charlamagne Tha God]

Trump advertised on Breakfast Club. He advertised on our YouTube shoot. He took me an envy and put us in a commercial or PAC did.

[Jess Hilarious]

Okay, now let me ask you a question. What did you, did you get any, any blowback? Because now people are mad. You got, you gotta dance with the dude that's in there. You know what I'm saying? So everybody mad. But only thing I'm mad about is I've been a black Republican for a long time. I'm an old school black Republican, but I don't know if I wanna.

[Charlamagne Tha God]

Did you vote for Trump?

[Jess Hilarious]

Man, listen. No, but, but I know a lot of stuff. I mean I've been going to conventions for a long time. I've been dealing in the world.

[Charlamagne Tha God]

What about 2016? You term 2016.

[Jess Hilarious]

No, I campaigned, I walk it back for you. I campaigned for Senator Obama to become President Obama, President Obama to stay President Obama. I campaigned for Hillary Clinton. I was at the dnc. I wanted Kamala Lewin campaign for her. But here's the problem. If these entities don't listen, if they think we ain't got to put no money down here in this community, we got them in the back. You don't have us in the bag. You must put the money down here. You must put the boots on the ground. So every civil rights organization, every Greek letter organization, everybody get back into the community. If you are not touching the community, we will not win this. And now they got to decide, is it going to be Gavin Newsome in the west with Shapiro in the east and come together Because I understand Shapiro.

[Charlamagne Tha God]

I'm not a Gavin guy. I like Shapiro though.

[Jess Hilarious]

Okay, tell me what. I love Shapiro, cuz Shapiro to Mero, he's Obama. To me he's Obama.

[Charlamagne Tha God]

I call him Baruk Obama. But you Bar.

[Jess Hilarious]

That's what they, that's. I feel like if you're gonna make a decision. I think the coach was a good dude, right? I think he was a good dude.

[Charlamagne Tha God]

Not me, but.

[Jess Hilarious]

Okay, tell me what you think.

[Charlamagne Tha God]

I didn't like Coach Walls. I don't think he added nothing to that ticket in no way, shape or form. I actually thought she should have went with Shapiro, but I think she, I think she was afraid of the blowback from the whole Palestine, Israel crowd at the time.

[Jess Hilarious]

Listen, man, did you like the coach? I, I like the coach also. We got a chance to interview his wife. I think they're good people.

[Charlamagne Tha God]

Good People, I think they're good candidate, but.

[Jess Hilarious]

But because I don't know why they made that decision. I've heard some things, but also you can't be afraid of. And I'm just speaking generally. It's nothing that I heard. But I'm reading the books that's coming out. And them books is juice. Political juice is ignorant. Right. But if you're afraid that somebody's gonna run for president, that is why you be the vice president. So you can run for president. And you gotta get it together to run. And you need to hit them battleground states. But if you notice something strange, like a lot of people believe that Elon Musk, you know, did something, you know, f dangled. I was gonna say a word with rigged on that part of it, but I'm trying to keep it casual with y'all. If we was Dr. I would have said it. But they say he did something, right?

[Charlamagne Tha God]

Yes. But you rigged the election.

[Jess Hilarious]

That's right. But if you. Even if you do that, you still cannot defeat the will of the people. What is it? Last weekend everybody was out marching. Then the dude from what is it JP Morgan say, look like we're going into a recession. Now they coming back to where they need to be. What is the point of all of this if people start speaking up? We can get this right, Right. You got to get yours where you can get yours. Now if I say you like my outfit, Jess, you like my outfit? Yes. Now I gotta say Amazon before the boycott, right? But a lot of small businesses about to get hit. Cuz you was getting all your stuff from overseas. What is my point to this? We have got to start talking about with racial issues, with financial issues, with characters. Character issues. So back to how did we lose? We're in those battleground states. People should have come together and told the truth. We ain't got the boots on the ground for you or you don't feel like Obama is something. And Obama got a right to say what he wants to say. And you can't get mad that this brother is trying to tell you something.

[Cheryl Underwood]

Right.

[Jess Hilarious]

You can be against it, but what happened to us sticking together? Let something happen to one of y'all. We, we riding. What time are we marching and where are we coming from? But if we are separated, we get a little bit of temporary money. But they got full power, everything, every branch of government. But they played a long game. They put people on the Supreme Court. Now you don't have no place to go. Now they telling law firms if you do anything I don't like we're gonna take the money. Now they telling colleges if you do anything, so what we gonna do? Okay, Everybody go to HBCUs now. You ain't got to do nothing.

[Charlamagne Tha God]

Basically what you're saying is we all got to get back to community because that's all we really got at this point.

[Jess Hilarious]

Absolutely. We will feed our own children, we will educate our own children, will talk about our history and make sure that it's out there. If you got to stand on Times Square on a crate like they used to do, we will educate the people. Because once you give it, you can take it away. And then when you get your ass in a sling, you want to do a distraction where you taking Harriet Tubman down from somewhere, then we all run over here mad while they doing what they really want to do over here. Don't fall for it, right? And then we got to be careful. Careful that companies that are making decisions for their financial bottom line. Let's go and talk to these companies. Go for real. That's what you think. Because at 12 midnight we gotta ride on you and give them a shot at going, well, I don't know. Well, we warned you and now we gonna ride and then we really gotta not do it because I miss McDonald's. I miss. I miss that fish for life. I do. I missed the fish for like Burger King. I miss you. I wasn't getting down with the impossible burger. You make it something.

[Charlamagne Tha God]

Why did the Talk get canceled?

[Jess Hilarious]

You want my personal opinion? I don't know. Because you know that's above my pay grade.

[Charlamagne Tha God]

I'm asking, right?

[Jess Hilarious]

You want my opinion?

[Charlamagne Tha God]

Yes. Yes. Yes.

[Jess Hilarious]

Well, I. I think we had The Dream Team 5. The Dream Team 5 was Julie Chan Moonves, Aisha Tyler, Sharon Osborne and. And Sarah Gilbert created the show, brought us to CBS and then here I come. That's the Dream Team 5. Eve Cat just as good, you know. So to me, once you get away from your Dream Team combination, do people really care and are we really talking about something? You don't have to argue politics. I think the View does an amazing job with what they do. Right? But we, we can't be that some people don't want to pick a side, right? Sometimes you don't want to argue all the time. But also I think we got to understand it is no longer visionary in a time entertainment. It is now corporation. In entertainment, if you are not cost efficient, yeah. You will not stay on. And if you're not generating revenue, you will not stay on. And I think once we lost the components that made. Made us great. Then we had to understand that it ain't your season no more. And beyond the Gates, I believe it was something that I was told from other sources. Christoph St. John, when he was alive, he was trying to put this together years ago. It's been in development for years. It's their time, it's their opportunity. People should support it. People should watch it and keep it on the air because at the end of the day, we all need the jobs. Now, would I like to do another talk show? Absolutely. Absolutely. I've found that I have the skill and I like doing it, but I'd like to do something a little bit different where I could talk about everything with everybody. And I just got a couple of.

[Cheryl Underwood]

Questions, you know, so what you joked earlier, you joked right on by to Sharon Osborne, and I clocked it, but I'm going to bring it on back.

[Jess Hilarious]

Real talk. That's why I told you when I walked in, what I say you. What's up with you? Did she ask me anything? Didn't I tell you ask me anything? Cuz you can ask me anything. It's how I answered. Okay, okay. Wait a minute.

[Cheryl Underwood]

So are y'all good?

[Jess Hilarious]

No. All right, we got that. Why we got sign? But I. But really, she got a sign that say, for me. Hold it up for me. Gonna be so ass. Like, I mean, I'm sorry. Okay, okay, okay. What?

[Cheryl Underwood]

Where y'all. Where y'all at now? Like, how is y'all relationship now? How is it?

[Jess Hilarious]

Listen, I wasn't mad. I'm. I, I'll tell y'all. Cuz I. Anybody ask me, I tell y'all. And I trust y'all.

[Cheryl Underwood]

Yeah.

[Charlamagne Tha God]

Remember talking to millions of people, Ain't just us. I just want you to know this.

[Jess Hilarious]

Family, it's millions of people. Come get them Mix and Mingle tickets. Hit me up on Instagram. Y'all know where I'm going. I'm New Brunswick, New Jersey. I need something, but I need to sell out everything. Tacoma, Washington.

[DJ Envy]

Got to sell that in California. Looney B in Arkansas.

[Cheryl Underwood]

Baltimore.

[DJ Envy]

Comedy Factory in Maryland.

[Jess Hilarious]

I've been Detroit at least three times. I need to sell everything to finance everything. But back to your question.

[Cheryl Underwood]

Yes.

[Jess Hilarious]

So remember they was Pierce and Sharon. They was talking about Megan Markham, and I, I pulled them to the side when he came on the show, I said, you cannot mess with her. Why? Her mama and them is Windsor. He Hills. She fell in love with a dude and now she living in Windsor Palace. You can't talk about her we have to ride on. You don't do this right. You can state your point, but you ain't riding on her like that. Well, they. He was riding. Then there was a cosign. The cosign called black Twitter, black social media, undefeated to this day, right? So they was dragging. And a lot of people don't like that heat, right? When I got in trouble, I had to go to the black community. I'm sorry, I was wrong. But then I found out I got caught up in something that I think God was telling me, something bigger is coming, you better prepare yourself for what's coming. So on that day, in that time period being dragged, then you want to come back in and say, I got something I want to say. Well, there was discussion about we going to ask you some questions back when people go, right, right, cool, cool, ask me anything. And then when it get heated and then you want to jump funky on somebody. Well, this day I believe that God said, did I not tell you, servant, that something is coming? Sit down. Why? Because if I had come out of a bag on her, if I had been the Cheryl Underwood from the past, that you know me, who the you talking. My last name is what I would have been a reflection on you. So just don't get the opportunity. Because black females else don't know how to control themselves.

[Charlamagne Tha God]

But sometimes you gotta check a motherfucker.

[Jess Hilarious]

But you gotta know how and when to check somebody. And on that day, the blessing from God was for me to sit there and when somebody say, what we gonna do, Cheryl? Because remember, I was moderating, which is the leadership position. I liked being the anchor, right? Julie Chan Moonvest was the moderator. I like being the anchor, right? She teared up for me. I take it down and we go to break. I slam dunk it and we go to break. If I ain't got nothing, I. Well, nah, if I got give her the signal, I ain't got nothing. That's a relationship. But if somebody's jumping on you sometime, you got to let them flame out. I love her. I love every woman and man that I've worked with. But when something like that happened, I think the blessing from God was, look how Cheryl has matured. Look what Cheryl did not do on cbs. When a black man is running it, right? We've got to understand we represent each other. Yeah, I could have lit her up. And for that moment, everybody would have been happy until they're not, right? So I think I did what I should have done, which was sit there and let you Keep talking. Let you keep talking now. Was I hurt? Come on, just. You know me. Who the you talking to? I wanted to go to break. I did. Do you. Who you talking to? But then I was like, shut it up, Cheryl. Shut it up. Go home, make a vodka tonic, ask God to take this heat off your back.

[Charlamagne Tha God]

And then she apologized. But then she went on stage, stage, still show, and said she regretted apologizing and actually said, fuck you.

[Jess Hilarious]

You absolutely. And see, to me, I would say this. Everybody wants to know my feeling. I want to know what was your reaction to. One minute you apologize, the next minute you not. One minute you fud. You for us, and the next minute you're not. One minute you making little comments about somebody in leadership, but you not. Or people are coming out with their information that they've witnessed. So wait a minute. Cheryl might not be the villain. Or. Or when. See, what happens is when you get power, even power on the level that we got it now, you become a threat, right? But we don't want to wield our power where you can't work. We need you to survive. So when people look back and go, cheryl, do you regret it? No. No. Who would have thought Cheryl Underwood from Def Comedy Jam bet Comic View would be on the number one network, the Red State, the Square Business Network, network that do all the police procedurals would be on a talk show. That's why sometime you got to know to play your position, right? And I. I think what I did that day was to represent black women who are going through this each and every day.

[Charlamagne Tha God]

So you ain't think about putting on a silk scarf, going on an Instagram live and just airing everybody out on the talk like.

[Jess Hilarious]

Like.

[DJ Envy]

Like somebody else up here.

[Jess Hilarious]

Well, listen. Okay, go. You go.

[Charlamagne Tha God]

No, I ain't.

[Jess Hilarious]

I ain't. It ain't. No. Come on. Come on. We here together. We here together. Talk to me. I think that you did what you felt was right for you in the Voice and the platform that you felt was right for you, right? But if you.

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[Jess Hilarious]

You learn so anything from me. They want you to be heated. They want you to get mad. They want you to attack your ally. Right? But why can't I pull you to the side and go. Can I say this? Okay. Hey, bitch, what the going on? You and this, right? What you trying to do? How can we help each other? But for me, I just want to live a better life. I just want the opportunities. I'm already walking in with my fist balled up because I'm a black female comedian. And everybody want to say, this is not fair. Of course it's not fair. You should be doing theaters alone. You should be doing stadiums alone. You should be doing movies. All of us. Tiffany had Monique. All of us should be working together and doing movies together. But the industry don't see the black woman as valuable yet. Am I right?

[DJ Envy]

Yeah, but you shouldn't have to walk into a building with your fist palm.

[Charlamagne Tha God]

Right?

[DJ Envy]

We should all be walking with our fist palming to make sure that we protect you.

[Jess Hilarious]

Yeah, but my fist is balled up because of an alleged slight. And that's the same thing in relationships abroad. Might bring in everything that the last dude did, but he come pretty Charlemagne. Which I was trying to get you back long time ago when you was a radio sidekick. I was gonna get you. I was gonna.

[Cheryl Underwood]

She was a real ugly show man.

[Charlamagne Tha God]

Thank you, baby.

[Jess Hilarious]

Drink that. Good day. I see you in the bathroom. I see you in the bathroom. I'm confused with your title. With Shay shirt and charlamagne. They different. I sample everything God have made on the buffet. I love. You know. You know, Guys, listen. Come on, Butterscotch. What you doing? What you doing? You know I got women like butterscotch.

[Cheryl Underwood]

Come on.

[Jess Hilarious]

Come on, baby. Demon. That's right. Right? That's right. Come on.

[Charlamagne Tha God]

That's what she said your name has in her phone. Where is this? That's.

[Jess Hilarious]

That's right. But my fist was balled up because there were things like not being able to get on certain TV shows, being blocked by who you think should be your ally, or I would have women blocking you. Yeah. And I have a strident personality as well, you know, I walk in a boss. Yeah. Because when you a female comic, you are the boss. You are everything. So I walk in. Sure. Can you do. No, I cannot read this right here. Just like when I did. What was the. What was the movie that Lisa Ray Jamie Players Club. Yeah. Okay. So they called me because in my past, I was doing a little sexual interpretive dance on the side. No, the part that Adele took, you know, I got. I'm too short to be diving. That wouldn't have been a good movie at all. Y'all would. Y'all would have walked out on the bootleg. What was your stripper name? I didn't have no stripper name. This what it was. You know I'm from Chicago, right? Yes.

[Charlamagne Tha God]

You know Cheryl Scripping, Right?

[Jess Hilarious]

Right. There it is. But, you know, I grew up in Chicago, so I was going to uic. They had an ad in a paper where you was go. It's right. It was lingerie modeling. It was lingerie modeling. And it was. Where you come out with the lingerie was in a tavern. Family den. It was in a tavern on Stony Island. And you come out.

[Cheryl Underwood]

No, but I know it's old for real.

[Jess Hilarious]

It's a tavern in there, Right. And I'm not a great hill walker. So I came out and everything. I got it on. But you had everything against you. Everything. Everything was against me. Everything. And God let you know what you. That's right. With the gun smoke. Listen, Festus James Arnett, listen to me. You better come up rifle man chap. Conor be fired roots when we start hating him, trying to get the money, right? Cause I'm trying to go to college, right? So I come out. But God let you know what you ain't supposed to do, right? So I come out and I know I'm not good at this, but them other girls, they doing it. They stripping because they buy the lingerie and then you're supposed to strip it off, right? But I'm. I'm not good. I'm garbage at this, right? So I start telling jokes and acting crazy and falling out the shoes. No, you have to walk around the tavern. So them hood. Do you know hood dudes like you.

[Charlamagne Tha God]

You crazy. You crazy.

[Jess Hilarious]

You need to go home. You need to go home.

[Carlos Miller]

You're not.

[Jess Hilarious]

So they start paying me for that and that. And that's. And that's how they were like, listen, you funny and you smart. And then that's when I started to have an affinity for the street dude. And I talk for the street dude. I Hang out with the street dudes, you know? And street dudes have backed me up in life. So, like you say, I didn't have to fight for myself because the street dud was always willing to step up. What's my point to this? I like doing nightclub comedy because my voice is relaxed, but I like to sprinkle. A little politics, a little spirituality, but it's 95% sexuality. Got Kyle Irby, Mike Washington on the show. So we can have some fellas on the show. Do I want to grow to doing casinos and theaters? I want to put shows together. It's a house party inside a comedy club. I would love for us to work together. You know, I'm the host and the headliner. But we got to find a way to make our own content with these fellas, and we have the platform to do it.

[Cheryl Underwood]

Yeah. And trust me, yo, it is not that hard because we ain't sitting around waiting for nobody to do it no more. That's the best thing about today's times. Like I've been saying, you know, how, like, back then, you know, you had the Harlem nights, right? But I feel like it could be something like that now. Not even with Jesus.

[Jess Hilarious]

I got the script, okay? I got the script. When I went through what I went through, hearing what I heard on the call, remember, I talked about the certain members of the Queens of Comedy dialing in on the call, and I really wanted to thank them. People criticized me. Why would you say that on cbs? Because you didn't hear the part where I said, thank you. Thank you for letting me see what I needed to work on in me, right? So I wrote a story, wrote about three to five pages. I had a script commission, and I said, I want to do this with all of us. Everything I produce through my company has comics in it because nobody's putting us to work. Have to hope that somebody fall out of a job to get a job. And I want to be able to make a movie in six weeks. Let's do it like they did in the 70s. Let's make these movies. Let's put them out there. Let's use the platform to promote. And let's pay our mortgages, let's feed our families. Let's get our retirement together while we buy property, while we change people's life and put kids through school. And if you don't want to go to school, let's give you a trade. Let's put you in music, let's get you in art. Let's do everything that was done for us, but we fund it. If you are wearing $250,000 around your neck, but you have not given any money to a hbcu.

[Carlos Miller]

That's right.

[Jess Hilarious]

Don't come to me when you in trouble. Because once they get ready to use what they watched you do, cuz they'll watch you do something and they'll let you keep doing it where you think you golden until they need you to be dismissed. There you go. There you go. So for me, and I'm going, get off my soapbox, cuz I'm trying to sell these, these tickets. I want to produce content. I'm not an actor. And people say, well, you did beauty shop. That was a blessing. That was a blessing of something that I could do. And Sherri shepherd helped me understand making a movie. And Queen Latifah allowed me to ad lib all of that monkey bread. She allowed me to ad lib. None of that was in the script. But what do I want to do now? I want to make content. I want to be the person to go, okay, Jess, I love your idea, but you didn't even read it all. I don't have to read it all. I know you're talented. I'm going to give you a shot. Your dream does not die for my dream to live. Walk down the business affairs, there's a white dude down there, you know, put some paperwork on you and let's get to work.

[DJ Envy]

That's right.

[Jess Hilarious]

I'm gonna get to work Monday because that's what I want.

[Cheryl Underwood]

Selling out casinos and theaters and all that. The only thing left for me is the stadiums. And so let's produce this content so I can get there to do that.

[Jess Hilarious]

Absolutely.

[Cheryl Underwood]

So we can do that.

[Jess Hilarious]

Absolutely. We need to be doing reality shows.

[Cheryl Underwood]

Yeah.

[Jess Hilarious]

Why are we not doing reality shows with female comedians in it? And I love the fact that some female comedians. I don't mess with Sheryl Underwood. Well, first of all, I ain't did nothing to you because I'm gonna tell you what your show does did. There was about to be some lawsuits flying and people came on your show on the Breakfit Club and told the truth about it. The truth is the ultimate defense. Oh, you better go back and look at your footage, cuz I ain't trying to bring that.

[Cheryl Underwood]

It's always a interview that got.

[Jess Hilarious]

You better go back and look at your footage. When somebody was this, When I was here was this. Back in the day, you don't mess with. You don't mess with me. And my thing is I don't care if you don't mess with me. I'm gonna walk up to you in love. Because one day I gotta face the master, and I want him to say, serving, well done. Why? Because somebody said they didn't mess with you. I'm not. I'm not gonna be no sucker. I'm not gonna be no gump. I'm. You know what I'm saying? But I will walk up to you. How you doing? You know, why don't we work together? You know, why don't we do something or. I got an idea. I've been in auditions where I didn't know you wasn't supposed to do this. I've been in auditions where they was like, well, sure, read these sides. Well, first of all, before I read anything, I'm really not good for this part. But you know who is good for this part part? My enemy is perfect for this part. I would name the person. I would name the person and I would go, go get that person or I'll give up a phone number. You don't really want me to do this. Y'all here, call this person right now. Don't tell them it's me, cuz they going to turn it down. Go get this person and get this money. Not cuz I'm trying to be noble because I just feel like I'm trying to right every wrong that I've done spiritually. And if you don't mess with me, let's sit down and squash it. Or let's get paid to squash it. Yeah. On a good reality show. Am I right?

[Charlamagne Tha God]

You saying a lot of good stuff. You saying a lot of good stuff. But I googled Cheryl Underwood wearing lingerie and ain't nothing come up, come back.

[Cheryl Underwood]

She just said. She just started hyper. She made her day up.

[Charlamagne Tha God]

I thought someone.

[Jess Hilarious]

Now I got one in a leotard I'm looking at back then. Is it the leopard leotard?

[Charlamagne Tha God]

No, this is you send you.

[Jess Hilarious]

I'll send you the leopard leotard. And then I had some. I. I did some AIDS anti AIDS posters. Matter of fact, I took those that did that photoshoot. Oh, no, no, no, no, no. They were sexy. They were sexy. Cuz I was trying to push condoms because I was trying to push condoms. I was trying to push condoms in a sexy way because my act is super sexual. You know me. I got one good move. I got one good move. Now, if you trying to make church on time, don't stop me.

[Charlamagne Tha God]

I don't like. You're a beautiful woman, Cheryl. Anti I'm thinking like, oh, no, it was sexy. Put somebody on there that miss you.

[Jess Hilarious]

We trying to put safe sex. And matter of fact, my father was alive and my father was like, so this what you're trying to do is. He called me his son cuz I'm his firstborn. He said, this what you trying to do? And I, and I. No, my father old school, like a mug. Old school, like, Like a mug, you know? He said, yes, that's right. And my dad would say, you know what? You know what? Don't let nobody tell you you're not pretty. Why? Cause you look just like your dad. And I was like, well, I don't know if that's a good thing or a bad thing, you know, but. And really who I'm doing on stage is my father and my oldest brother. Wow. Oh, my father funny. Oh, my father say wild stuff like, I don't know. Can I say the word? You gonna beef him out? Yes.

[Charlamagne Tha God]

I heard what Gayle King just said.

[Jess Hilarious]

You okay?

[Charlamagne Tha God]

Give me what Gayle King said already.

[Jess Hilarious]

Didn't date him. Okay, listen, I love the fact that Gail done turned into a goon. I love.

[Charlamagne Tha God]

She's 70, she ain't got no can.

[Cheryl Underwood]

She don't care who checking her.

[Jess Hilarious]

But listen, I want to be. We want to be making that Gayle King money. I know. Yeah. I don't know if I want to go in space. You know, I'm cool, you know?

[Cheryl Underwood]

No, she. Boy, she got too much money.

[Jess Hilarious]

Right? That's when. But would you do it if they.

[Cheryl Underwood]

If they said no, I wouldn't go in space. I think space is for space and Earth is for Earth. I'm good.

[Jess Hilarious]

Yeah, I think I'd be okay. Yeah. Cause I, I don't do nothing either. I'm doing the Tom Joyner Fantastic Voyage cruise. Me and my doctor trying to go on. Well, I'm doing that because we're going to talk about relationships and everything and my doctor's going to come on and I want people to ask questions. I would love for somebody to do segments where we really talk about healthcare, we really talk about the new things that are out there, because everybody eating healthy and walking is not going to do it. If you've been tearing up your body for years, you need medical care and we need to be making these pharmaceutical companies and make it more reasonable for us. But, yeah, I'm going on there. But I love what the foundation is doing for HBCUs, because I have my, my own foundation Pack Rap foundation for Education. And I have a Sports initiative for young boys. So I'm going back through my Rolodex of everybody. I was kicking and waiting. Well, now that you're married, give me some money for my foundation. You know what I'm talking about.

[Cheryl Underwood]

But we just found this. And it says Samoa says Cheryl Underwood has ulterior motives. I don't rock with her like that. I'm not phony.

[Charlamagne Tha God]

I saw that.

[Jess Hilarious]

That's what you tell me now. But she did admit that there was a phone call. She admitted that there was a phone call.

[Charlamagne Tha God]

I remember Adele said she wanted. Didn't Adele said she wanted to sue y'all for something?

[Jess Hilarious]

Okay, how much? I.

[Charlamagne Tha God]

She put it.

[Jess Hilarious]

Put two and two together, you ain't gonna get five. You see what I'm saying? So. And I wasn't. I wasn't mad about that because you could go viral for a negative thing or a positive thing. Right? And so when it was coming out and everybody. I'm a Sue. I'm a Sue. I'm a Sue. Truth is the ultimate defense. I didn't. And I said, based on my recollection, I'm not against you. I would love for me and Samora and Adele and Monique and Justin, all of us and Tiffan, all of us work together and make a movie. I would love for us to make a soap. I would love bad their stomach to.

[Cheryl Underwood]

Be hurting if they have a movie with all us in it like that.

[Jess Hilarious]

Yeah, we fighting. We doing everything. The script I got. Oh, we fighting. We doing everything. Making love everything. We doing what the dudes do in their movies. But if we can get the financing, that's the key. Because people think they're going to lose money. Why a woman will pay to see a male comic with her man. Sometimes men don't want to come because they think it's going to be an hour and a half about fashion. Right? We gonna tap you a little bit. But my show is created for the male audience, where the females will learn. Because I'm sitting with your dude.

[Charlamagne Tha God]

I thought we would have saw more of that after Girls Trip. Girls trip did over $100 million.

[Jess Hilarious]

Right. You know, why do you think it didn't happen?

[Charlamagne Tha God]

I really don't know. Well, I don't. I really don't know. I thought. I thought that that would make sense for people to start doing more of.

[Jess Hilarious]

That just because they duplicate. And I would say, as a business person, person, sometime. I'm not saying take less money because you think you less than, but I'm saying sometime your cost. If it And. And I look at it like this. So I want people to call in, criticize me. Just like when I was on Club Shay, and people criticize me for things. You got a right to say what you feel as long as you stay listening. Time spent listening. That's what I need you to do. But here's the catch. If you're not making any money, so then you get a shot or a job offer, and then you ask for your catch up money. You trying to catch up to all the money you. You didn't make. Then you close the door on them hiring us because your price is too high. You see what I'm saying? Sometimes you got to be a cost effective, not cost prohibitive. When I go for a job now, people say, well, do you think you're going to make the same money? He was making a cbs? Absolutely not. I got blessed. Somebody saw me on cbs, and I think they saw me on the View doing political humor, right? Then I got a call. No nowhere do you hear Somebody gets a phone call, avoids the phone call. Steve Harvey goes, bitch, call him back. Because me and Steve chop it up like that. We've been friends for years, right? So I call back, I go to a meeting, and in 72 hours, you have a job that you keep from season two to season 15. That's God. And that's also being ready for the opportunity. And then I can show that if I can do it, Jess can do it if I can do it, Tiffany can do it if I can do it. But Monique should be able to be on the show. Lonnie Love. Yeah, where's Lonnie Love with all of that experience, right? Sherri Shepherd. We got to help Sherry keep that show on the air. Jennifer Hudson, everybody. Because the industry is not like it used to be. And. And that's partially the dismantling of urban radio. Why music ain't the same, right? So now they're saying, well, I'm not gonna make a video. You gotta do it yourself. Okay, I'll do it myself. But how do I make a certain amount of money? Now everybody wants to talk about streaming.

[Cheryl Underwood]

Yeah.

[Jess Hilarious]

And the finances of streaming. But then you think somebody gets this. What I'm saying is we need to go back to what we used to do, learn the business, work with them while we create our own. Because they gonna come and buy you from you when you come, open a briefcase like Hawaii Five zero and give me my money. You see what I'm saying? And we can do this. And you all are part of helping us do this because we have to be able to promote. I want people to buy tickets to come. I want younger people to come in. But I'm really an old school school at.

[Charlamagne Tha God]

Yeah, what about us? Everybody always forgets about the 40 somethings and the 50 something.

[Jess Hilarious]

Absolutely, absolutely 50 somethings. But once you get to a well placed oral sex joke is a young dude being okay, old ladies, what they call auntie's still getting head and I'm still throwing it. And I'm still throwing it.

[DJ Envy]

And she's performing this week in New Brunswick.

[Charlamagne Tha God]

Yes, you'll be a distress factor but.

[Jess Hilarious]

Make sure you go, what we miss? What we miss?

[Charlamagne Tha God]

Gail King on cbs.

[Jess Hilarious]

Now. What in the are you talking about? Oh yeah, listen. And I love when Gail, she got that cool corporate voice but something gully come out of her mouth. That's the, that's the kind of Gail that I want to slap and go, let me see what's in. Yo, that ain't ice tea. That's.

[Cheryl Underwood]

That's because then she came back with a.

[Jess Hilarious]

What does that mean?

[Charlamagne Tha God]

Right?

[Jess Hilarious]

Like you don't know. You a journalist, you know.

[Charlamagne Tha God]

Exactly.

[Jess Hilarious]

You done say it that three, four times. Stop playing. You don't say that while you patting your head. Gail, stop playing. Stop playing. Gail like this. She knew what she was saying. You know, I was thinking Gayle knew.

[Cheryl Underwood]

You might not know what the effort mean, but you know what the dyker tree mean. Cause I ain't know if Gayle was, you know.

[Jess Hilarious]

Well listen, I don't believe that. Let me tell you something.

[DJ Envy]

What is going on?

[Charlamagne Tha God]

That was a good point. Just bring up because they've been saying Gayle part of that community for so long her Oprah, that she should be able to use that word.

[Cheryl Underwood]

That's what I'm saying.

[Jess Hilarious]

Listen, everybody, they try to say, first of all there is something to be said about once you make a lot of money and you get famous, then everybody's talking about that's what you are. Cuz you don't see what I'm doing. Look, I creep on the low, you know, I go through three hotels at one time. Listen, meet me in the lobby of this one. We gonna get in the cab, we're gonna go down to this one. But we're not gonna stay. We gonna go out the back. Then I want you to go around the corner. Now you got to drive another car. I don't want everybody knowing my business. So people were trying to say I was worth all that, Cheryl. But they were saying that I was. But is it worth all that.

[DJ Envy]

You better tell them it is.

[Jess Hilarious]

It's all right. I mean, I. No, I tell the truth now before we. Before you. Cheryl, let me take you out to dinner first. I tell you it's garbage below the waist. Garbage. I ain't got to move above the neck. Fire. You'll be late for work. You'll be late for work. You late for work. You'll be mad. You'll be mad. You be like, what day is it? And my kidney is gone. And my tooth, my wisdom. You took my wisdom tooth out. I put you down. I put you. I put you down. I make you call me. I make you call me. And I don't need a full face of makeup. I know when I did a good job. When they don't care whether I got a wig or makeup on it. I just need to see you. I bet you do. I bet you do. I know. I know what I. I know what I'm doing. But. But fair exchange, ain't no robbery. Now I tell you the truth. You want this? It's not good. You have to find somebody good. I'm at the top. I'm not at the not about. And see, I would hang out with Gail cuz she said she looking for somebody, but she's going to have a hard time.

[Charlamagne Tha God]

Why you say that?

[Jess Hilarious]

Successful women are going to have a hard time because some men think we don't need you. I need you. I need you. You can work at the gas station and I need you. Why? Because I know I'm getting honey buns. I'm going get barbecue chips and a full tank of gas. And then I'm going motivate you to buy the gas station you work in. And then I'm going motivate you to buy more gas stations.

[DJ Envy]

That's right.

[Jess Hilarious]

If that's what you want to do. Now if you cool working at the gas station, I make sure your shirt is fresh and iron, Nate, because your real name is Nathaniel. I'mma. But I always say Nate, I'm sure I make sure your shirt is ready. Give me some. Some sugar. Now go work at the gas station. I'm going to scoop around, get me a tank of gas. I need that 91 octane, baby. And I'll see you later.

[Cheryl Underwood]

And see, and people be wondering why these young be liking these older women that listen.

[Jess Hilarious]

What?

[Cheryl Underwood]

She just.

[Charlamagne Tha God]

Brandon been over there blushing the whole time.

[Jess Hilarious]

What you trying to do? What you trying to do? What you trying to do? Wait a minute. Who on your show? No. Oh, boy. Oh boy. What's his name, what's his name? He's in all the commercials now. Big dude. Big dude.

[Charlamagne Tha God]

Drew.

[Jess Hilarious]

Yeah, yeah, listen. Everybody was blowing my phone. Drew Ski trying to hit. I was like, where at?

[Charlamagne Tha God]

Y'all know Cheryl?

[Jess Hilarious]

What's her name? Cheryl?

[Charlamagne Tha God]

She dark skinned lady.

[DJ Envy]

Cheryl Underwood.

[Charlamagne Tha God]

Cheryl Underwood.

[Jess Hilarious]

She got that thing actually.

[Charlamagne Tha God]

Yeah, he said he wanted to hide Underwood.

[Jess Hilarious]

Everybody was calling me, going juicy, said he want hit. I said, bet. Well, let's call him, tell him what's up. I'm in this city. No, I don't. I don't know how to do all that.

[Charlamagne Tha God]

Man. Who the hell be DMing me from your page all the damn time?

[Cheryl Underwood]

Oh, that be me.

[Jess Hilarious]

Wait a minute.

[Charlamagne Tha God]

But did you Instagram?

[Jess Hilarious]

Wait, but wait a minute. Let me tell you what happened. Remember I said, is this still you? Yes, I'm secret. Is this still you? She wanted to make sure. Like, I'm not saying nothing, man, I need to come on your show. But she think, yo, she act like we got a different number or something. She still you? It still work?

[Charlamagne Tha God]

Yes, I'm. I'mma connect you and Drew.

[Jess Hilarious]

Okay, but listen. No, y'all need to. What y'all need to do, we need to meet up somewhere. Y'all need to film it. See, it's not just documented. And that thing. Now I need to get that kiss good night, cuz I. I like the kiss. I don't really like to do nothing now, you know, me and flight, he escorted me to the BET Comedy Awards. Daddy. Flavor Flav. Yeah, he escorted me and he was like, you know, he thought he was just doing it, you know, being dashing and everything. But then when I did my set, the one that La Cool J performed on way back in the day, when I had my little makeup, my outside makeup, and one of the Wayans brothers had me in the corner, they was rapping to the beat. I said, you know this is Cheryl Underwood, right? And he was like, sir. I was like, yeah, man, you still trying to. You know, because, you know, usually I don't look, you know, but I got the best. Dale McDonald, best glam man. Three Emmys to my one. So anyway, you know, I was trying to get my. Get myself together and, you know, I'll be texting people and I don't know if people really like me, right? You gotta figure out, do you really like me? Because I'm not gonna throw it out there if you don't like me. And if you like me, then let's go out now. If you want to film it, film it. So Me and Flav get together, I do my set. Then he's like, well, come to the after party. I said, no, I'm going home. Go to bed. He said, no, come to after party. We have a good time. This dude was getting drinks, everything. He was chivalrous, everything. So I was like, okay, it's time for me to go. You know, I said, good night. And he was like, good night. And so he moved in for the movie. And I said, all right. You buying them drinks. Bought a lot of drinks. And I'm still standing. Okay. And we kissed good night. And I was like, well, damn.

[Charlamagne Tha God]

We said favorite. We said favorite. Trade exchange. What you say?

[Jess Hilarious]

Fair exchange. A robbery.

[Charlamagne Tha God]

Fair exchange.

[Jess Hilarious]

A robber. It ain't no robbery. You trying to holl at me? But he was dashing for me. You get me on? Dashing. Handsome a man, right? I'm. I like a baby. The boss. But. But people think, why would you mess with Flay, right? He was dashing, he was handsome. And I felt it was an appropriate goodnight kiss. It don't mean we gonna be together. Cause you may not like me. You might just have a feeling. You know what I'm saying? And if you got the feeling, what you wanna do after this? There you go, Dresky.

[Charlamagne Tha God]

Don't you get scared? Yeah, I'm putting the pressure on. Don't get scared.

[Jess Hilarious]

But we gonna have to come back here and y'all gonna have to let the cameraman follow us, you know, figure it out. Cause we hit the Red Lobster in Times Square and tear them apart. Ain't gonna be no more crab legs. He better do.

[DJ Envy]

He better do something other than Red Lobster.

[Jess Hilarious]

Help the brother. We trying to help the brother. I would make the Red Lobster if you go to my Instagram page. I've been going to Red Lobsters with people all over the country with dudes. If you want to date me, and I'm in the city and there's a Red Lobster I'd like to go on Thursday night because I need to get some sleep, do the promotion on Friday. But I want to go into the Red Lobster, cuz we got to bring that back as the popping spot. We got to help this brother. We got to talk to the brother. Over at lows, we got the brother that's running lows. We ain't talking if you are on the list. We need to talk to you.

[Charlamagne Tha God]

Cheryl, not wrong. If you get anything from this conversation today. That's what we got to do. Bring community back.

[Jess Hilarious]

That's right. That's right. Okay, so When I'm coming back. When I come back. Listen, I. I ain't trying to take a position. Oh girl, I. I just try to.

[Cheryl Underwood]

Get in because I need to try to do that.

[Jess Hilarious]

Well, no, I don't get down like that. I don't get down. And you don't train your replacement. I got jokes about that too. So my walk up to teach me how to run a copy machine. That's a copy machine? I thought that was a vending machine. I ain't never seen tickets.

[Charlamagne Tha God]

Stress factory in New Brunswick.

[Jess Hilarious]

This Friday, get your tickets and go to.

[DJ Envy]

Go to.

[Jess Hilarious]

That's it. That's me and flag.

[DJ Envy]

Okay.

[Jess Hilarious]

And look, look. Look at that. That's a makeover.

[Charlamagne Tha God]

You look good, girl.

[Jess Hilarious]

Yeah, that's a makeover right there. Listen to me.

[Cheryl Underwood]

No, no, no.

[Jess Hilarious]

I was trying to get him cuz 2 chocolate people usually don't get together. Yeah, but he had all his skin was the same color. I was here.

[Cheryl Underwood]

No, you don't look like Loya. Lo look like you.

[Jess Hilarious]

Yes, well, you know what? I would love to meet. I would love to meet him and chop it up and everything. But let's see what we going to do. Cuz I. I need. I need another check. I need to make some money. I come to New York once a month. I come once a month.

[DJ Envy]

Come on up once a month.

[Jess Hilarious]

We need to talk politics too. Let's do it.

[DJ Envy]

It's the Breakfast Club.

[Jess Hilarious]

It's a Breakfast Club. That's right.

[Carlos Miller]

Wake that ass up early in the morning. The Breakfast Club.

[Coca-Cola]

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[Carlos Miller]

Taking control of your career is empowering. Just don't tell my boss I said that. Just kidding. I am the boss. This is Carlos Miller from the 85 South Show. And building a career isn't just about a job. It's about creating a path that impacts our community and future generations. Whether you're starting out or even making big moves, State Farm is here to support. Support you with resources to help protect what you're working hard to achieve. They've got your back every step of the way. Because, like a good neighbor, State Farm is there. Find out more at statefarm.

[Jess Hilarious]

Com.