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Cheryl Underwood
The wild, wild west.
Matt
Yeah.
Cheryl Underwood
These are all your crew?
Matt
Yeah.
Cheryl Underwood
See, it's the same way with us. Everybody work with crew, keep confidences. Don't talk too much.
Matt
Now they talk we. These three are a problem. They get a couple whiskeys every night at the open mics. Or not the open mics, you know, I mean, but they tell stuff. Oh, yeah.
Shane
They fight amongst each other.
Matt
When they fight amongst each other, immediately my.
Cheryl Underwood
Well, no, mine started negotiating and gang up on me. I'm like, who the say I would
Matt
cut their heads like this? The second they unionize, they're dead. Like, they're dead.
Cheryl Underwood
This a no union. No, this. We got to get along great. I'm going to try this with they asses.
Shane
It'd be like Napoleon's cannon right into
Matt
the French people's grape shot right away. Yeah, actually, I know Kyle from. This is a. This is a. So you ever hear I talk about the time I was at the Laughing Skull Comedy Festival and I was in the green room and it was the men's U.S. soccer team just lost, and one of the lady comics walked in and was like, the men's team lost? They suck. I guess they still get paid more than the women. And I was just the one guy who's like, well, it's because they're. They're not as good. And there was one guy in the room with me that was like, don't do it. I was sitting next to me going, why are you doing this? And I was like, hold on a second. Had to be done.
Cheryl Underwood
You try to warn him not to say.
Matt
He was like, don't. You don't.
Cheryl Underwood
Why not? He is. He is our Jim Kelly.
Matt
We were in the wrong room for it.
Cheryl Underwood
Well, why?
Matt
Because it was just.
Cheryl Underwood
It was a bunch of women.
Matt
Yes. And even the guys were women. Oh, yeah. The whole group, every single guy in there was like, well, women are just as good at sports. Yeah. Just like you. You never played sports.
Cheryl Underwood
Once you see a bitch get cte. I have respect.
Shane
I think they're born with it.
Cheryl Underwood
But see, to me, here's my feeling. If you want to be equal, you will be treated equal. And you don't want equal because equal is the same. And that's what everybody. How you want to be equal? No, you don't. No, you don't. The time that a motherfucker get off the bus. Remember, we talking about the Pistons and Lambert and them if somebody get off
Matt
the bus and choke you and put
Cheryl Underwood
you in the face. But we not even on the court. We just fighting in the parking lot. You can be equal.
Matt
Yeah, I like it.
Cheryl Underwood
Yeah.
Matt
Maybe the WNBA needs. Actually, they've been fighting a lot. That's what got a lot of. That's actually what picked the league up.
Cheryl Underwood
Do you think that they. But I think that there's certain things, like me being a female comic. Women will come to see a man, right? With a guy. It's difficult for a man to come to see a woman. And it's an hour. That's why we end our show the way we end our show. It's an hour and a half of many shit. So what guy is going to bring a group of his friends to go, let's go see some women, bash us for an hour and a half and pay for it and get two drinks and some chicken wings. Who wants to. What man wants to do that?
Shane
Guys.
Matt
Yeah, there's some gay guys.
Shane
Pretty true, though.
Matt
Gay guys and sickos. Maybe this guy.
Cheryl Underwood
See, I know gay men that. That I get along better with a certain type of energy. Right. But I know gay men that don't want to be represented the way the stereotype is.
Matt
Yeah.
Cheryl Underwood
I know gay men that fix cars. I know gay men. Are you gay?
Shane
No.
Matt
Yes.
Cheryl Underwood
I say, that is so cute.
Shane
Explaining allegations.
Matt
Yeah, they.
Shane
They just.
Matt
He twerks. It drinks, twerk. I forgo twerked at Drake.
Cheryl Underwood
I didn't twerk at Drake.
Matt
Yes, he twerked at. I had to grab him. I go, no, no, no.
Cheryl Underwood
You were twerking at.
Matt
He's just saying. Hold on a sec. Were you dancing when Sexy Red came on and I had to grab you and go, dude, I.
Cheryl Underwood
But.
Matt
But I wasn't twerking.
Cheryl Underwood
It was the. It was just the. You was doing your version of twerk.
Matt
Oh, no, I do have a little move.
Cheryl Underwood
I bust out.
Matt
But it wasn't.
Cheryl Underwood
You was doing the Humpty Dance. It was before Sexy Red came on. I was already.
Matt
It was while Sexy Red was on.
Cheryl Underwood
Then the. Then the DJ pivoted to Sexy Red.
Shane
Hold on.
Cheryl Underwood
You was doing a Humpty Dance. You was doing the dog.
Shane
The key question is, how low did you go?
Cheryl Underwood
I didn't go low at all. I didn't drop it one inch. Don't make that face.
Matt
You thanked me.
Cheryl Underwood
Well, yeah, I almost danced a Sexy Red. I did appreciate that, but it was.
Matt
It came crazy.
Shane
Did you stick your tongue out?
Matt
Yes. He was looking at me going,
Cheryl Underwood
you love him. Are you in love with him? Am I in love with Shane? Yeah.
Matt
Yes. Yeah. It's the funniest thing. Not gay, but yes. We all love each other. It's my guy. But he did twerk at drinks. But I didn't. But I didn't twerk.
Cheryl Underwood
So you and Tony Hinchcliff have sex together?
Matt
Yes. Why are y' all doing this to me?
Cheryl Underwood
That's gonna be the rumor. I'm about to live in this now.
Shane
Oh, no.
Matt
But Lamar is the freakiest of the group.
Shane
True.
Matt
Yes.
Cheryl Underwood
Beth. Really?
Matt
Yeah. No, tell me nothing.
Cheryl Underwood
What do you do?
Matt
He'll tell you. Ask him one more time, he'll tell you something. He'll tell you something crazy.
Cheryl Underwood
What's the freakiest thing you do?
Matt
Oh, yeah.
Cheryl Underwood
Are we recording all of this?
Matt
Yeah, absolutely.
Cheryl Underwood
What's the freakiest thing?
Matt
I. I tried to go to an orgy in Milwaukee and it didn't work out. That's a good one. Yeah, I. Like, I knew you're gonna say something crazy.
Cheryl Underwood
Orgy in Milwaukee?
Matt
Yeah. He was with me in Milwaukee, and he got on the Internet and tried to find an orgy, and then he wrote a. I think a Uber. Took an Uber to a. A hotel. They said, yo, if you give us 50 bucks, you can come to the orgy. And they just stole 50 bucks from him
Cheryl Underwood
to me. See, that sound like a setup.
Matt
Yeah, Ye.
Shane
But here's the question, Lamar. What would you have done had you gone there?
Matt
I don't know, man.
Cheryl Underwood
He would have everybody That's a buffet for this. It's the buffet of sex. He like, oh, yeah, fill it out. That's it. The Uber was what, five, ten dollars?
Matt
It wasn't much.
Cheryl Underwood
The entry fee to the orgy is 50.
Shane
Yeah.
Cheryl Underwood
Are you having a good night?
Shane
There does have to be the Alaskan crab legs of the orgy. Let's save some of that for everybody.
Matt
Here's the funniest part about the people that ripped off was we got back to New York and he. He confronted them online, and they were like, actually, where are you right now? He's like, I'm in New York. And they're like, you're not going to believe it. We're having an orgy tonight. 50 bucks.
Cheryl Underwood
What, did you vimbo on the money or something?
Matt
What you do the first time
Cheryl Underwood
you sent them the money online?
Matt
Yeah.
Cheryl Underwood
Okay. Rule number one, you don't. Don't pay before you. Well, leave it on the dresser. You're supposed to leave it on the dresser.
Matt
They have deposits nowadays.
Cheryl Underwood
Okay.
Matt
You gotta do a deposit.
Cheryl Underwood
Really?
Matt
Yeah.
Cheryl Underwood
Is that what we doing now?
Matt
Not me.
Cheryl Underwood
I mean, but that's what the bitches. Or was you fucking a man?
Matt
No.
Cheryl Underwood
Okay. No.
Matt
There was gonna be some fellas in there. I'd say three to one guys. Yeah.
Cheryl Underwood
So then how many people would have been in the orgy?
Matt
I think you got at least 10, right?
Cheryl Underwood
10 people, that's $50 a pop.
Matt
I was just.
Cheryl Underwood
That's 50 a pop. That's 500. That's a good night.
Matt
Yeah.
Cheryl Underwood
Who get the money though? That in Milwaukee? That's good.
Matt
I don't know.
Cheryl Underwood
What are we supposed to be talking about?
Matt
I'm sorry. This is exactly what we always talk about.
Shane
It'd be nice to have host a non existent orgy, get 500 bucks and just jerk off by yourself in the hotel room.
Cheryl Underwood
Yeah.
Shane
Just be like, I made so much money tonight.
Matt
Yes. It's awesome. That's a good plan. Yeah.
Shane
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Matt
A rough one.
Shane
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Matt
Yeah. Now you know the crew. Yeah.
Shane
Yeah, that's pretty much.
Cheryl Underwood
Yeah. Your crew is probably similar to my crew.
Matt
Yeah.
Cheryl Underwood
That's why they only smile and they like, don't tell our business.
Matt
Why? What are they into?
Shane
Yeah, what the hell?
Cheryl Underwood
I. I would say. I would say I have the best team in the business because we understand each other, we respect each other and they keep my secrets.
Matt
My team sucks. They don't respect me. They tell everybody everything and then they fight each other every night. These guys have three shots of whiskey and go motherfucker.
Cheryl Underwood
Really? Well, maybe y' all want to fight each other. Dale and Kyle now. No. Y' all good.
Shane
So you guys are tight knit?
Cheryl Underwood
Very much so.
Shane
That's nice.
Cheryl Underwood
They're. They're like the big brothers. They nudge me out of my comfort zone. Like doing Netflix and even considering a special, I'm very afraid.
Matt
Yeah. Because scary. Everything's scary.
Cheryl Underwood
Why? Why?
Matt
I don't know. Putting yourself out there sucks.
Cheryl Underwood
So you've. How many have you done?
Matt
I've only done two. I've only done one Netflix special.
Cheryl Underwood
Okay. How do you feel?
Matt
I was nervous and then once I Did it. I was. What made you nervous putting yourself out there. Anytime I make anything and it goes out there, I'm like, why would I ever.
Cheryl Underwood
Cause for me, I'm more comfortable in a nightclub, for sure. Cause the language can be relaxed and it's intimate. And if you lose them, you can get them back in a special. Now it's fixed in stone. But I will say this. When Jamie Foxx and Marcus King produced this show, laughapalooza, and it was filmed in Atlanta, and me and Mike Washington had been going around doing shows right after September 11th. So I was doing some pro American, pro President bush jokes about September 11th in a very hood way. And everybody else in Atlanta was getting up and doing traditional sets, nightclub sets. And I told Jamie, I said, I'm going to bomb. He was like, why do you think that? I said, because I'm about to do some pro American jokes and pro president jokes. Because I used to get booed talking about being a Republican and supporting President Bush. But once I did it, and the response, Kyle, you. Because you were saying, Kyle's sitting off camera. But it made you respect me more in that humor.
Matt
Yeah, that's when I saw you was not just. That's when I realized, oh, titties and suck a dick.
Cheryl Underwood
You.
Matt
Oh, she got a. A strong mind. I didn't know that.
Cheryl Underwood
But here's the thing I know that
Matt
doesn't sound right at all.
Cheryl Underwood
I have a rule. I'm gonna take this off ramp. I have a rule. I don't. I don't sleep with a fuck or engage sexually anybody. I pay because I'm getting fucked twice. Yeah, you don't fuck who you pay. If you want to be in a relationship with me and you work for me, you must quit. And then we'll see where it goes. But in hearing when we got to know each other and the jokes that he appreciated, I had to take the risk and I needed it to be recorded so it could be timestamped. But when you recorded your special, did you bring back any jokes that had been recorded or done somewhere else to put in a special?
Matt
No.
Cheryl Underwood
Really? You wrote.
Matt
No, but I only did the only thing I had before that was a YouTube special. So I didn't have anything ever recorded.
Cheryl Underwood
Really? Really.
Matt
But I. I don't think there's a problem with that.
Cheryl Underwood
Really?
Matt
Yeah.
Cheryl Underwood
And then you and I were talking, and like, I. I talk in my show about being a Republican but being considered a rhino, being considered transphobic, being considered homophobic.
Matt
There's nothing wrong with being considered that. I get considered everything.
Cheryl Underwood
A Republican in name only. So in this. This administration, I've been a registered Republican for decades. Right. But in this administration, the Trump administration, I'm considered a rhino. And. Which doesn't bother me. I just feel like one thing I love about the power of comedy, it's great discussion. You know, you're not gonna agree. You're not gonna like every joke I tell, you know, and you're not supposed to. You're supposed to have a certain type of reaction to certain things. What I ask the audience to do is sit through the set and figure out what you like and what you don't like, but let everybody else around you enjoy it.
Matt
Yeah, that's fair.
Cheryl Underwood
Yeah. And if you don't like it, because I was like, really, like, one of my first jokes was, what? Go good with chili.
Matt
What?
Cheryl Underwood
We'll go good with chili. Now that you brought up white people, let's talk about the ass.
Matt
That's fun.
Cheryl Underwood
That's one of my first jokes that I was telling.
Matt
But, oh, how did the Bush jokes go? I bet people were pumped.
Cheryl Underwood
Well, they. Well, the way they were told.
Matt
Yeah.
Cheryl Underwood
Yes, they were. They were really stoked because they were told in a way that the urban and the black and the street Atlanta audience could understand. It's not for you to agree, but the president is the president. Like, if it wasn't Trump saying a lot of shit, we'd be like, right, right. Crypto. Right. Let's get in on this. Or. Right, right. Let's fuck these motherfuckers up before they get a nuclear weapon. Right. It's who it's coming out of sometimes and the times that we live in. But I think that's why I said what I said at the roast. You're not gonna agree. It's a roast, and it's a new generation of roast. It's no longer Rimshot, Don Rickles, Dean Martin, Pearl Bailey, Lucille Ball.
Matt
And it wasn't in a small room where we're all friends. It was in an arena on national television. We never met.
Cheryl Underwood
That's right. And it's international. Right. But what I liked about it was you could see the camaraderie and I think even talking about the George Floyd joke that Tony told. But I believe on the side of the cookout crew, Pete Davidson represented with the Charlie Kirk joke.
Matt
I agree. You gotta be offended by both or neither. That's how I felt about that.
Cheryl Underwood
That's right. But you should be. The reaction should be offense. The Floyd family should be upset. There should be A crew of people that are, that are mad because that's the reaction you have, right? Because you're not thinking about freedom speech. You're thinking about your brother who was murdered. Yeah, by a system. But on the same token, I tell people it's a roast and it's a new generation of roasters. Because everybody's like, sure. How did you feel that they talked about your dead husband committing suicide? Okay. It really, truly happened. And it happened over 30 years ago.
Matt
So I called you.
Cheryl Underwood
Yes. That's why.
Matt
For the record.
Cheryl Underwood
Well, remember when I did all the interviews?
Matt
Ever do that without. Yeah, yeah.
Cheryl Underwood
But let me tell you something, Shay. Knowing you, knowing Tony, like I'm sitting next to Tony. This is ordering Crown and coke. And I'm like, so people think you're a bigot, but you really a black man? You, you, you look like it's a black pimp.
Shane
It's a black pimp. That's ex has a throne. He has a throne.
Matt
He has like two or three different gold thrones. I was, I was there two nights ago.
Cheryl Underwood
You lying.
Matt
It's the literally the blackest place I've ever seen in my life.
Cheryl Underwood
I'm telling you. That's the feeling I got sitting next to him. I was like, you're black. You. You either something. Who beat him up in school?
Matt
I think a lot of people. I think he got his ass whooped a lot. If I had guessed
Shane
it was like a spider man bite.
Matt
He's just kept getting beat up and
Cheryl Underwood
see to me, I would love to see Tony and Cat Williams in a buddy cop movie. That would be hilarious. Two little with big attitudes in a movie. Yeah, it'd be great.
Matt
That would be very fun.
Cheryl Underwood
Remember I told. I think you need to remake Smokey and the Bandit.
Shane
I like it.
Matt
That'd be nice. I'm usually getting John Candy. I get those a lot. Don't hit me with those.
Cheryl Underwood
I don't see.
Matt
Well, I lost a little weight.
Cheryl Underwood
Yeah, but even if you were husky or you have a. To me, you have a swag. Yeah, you got a swag. Yeah.
Matt
No, no, I get it, I get it.
Cheryl Underwood
No, I mean, you, how tall are you?
Matt
Six, three.
Cheryl Underwood
How much you weigh?
Matt
240.
Cheryl Underwood
Okay. When I was five. Two at 250. Yeah, I fight 250. Hell yeah.
Matt
Nose guards. Jesus Christ. You're in the A gap. Yep. It's will for
Cheryl Underwood
but I, I, I
Matt
think Cheryl Underwood knows tackle the Ohio State.
Cheryl Underwood
No, I gotta put the ball, I gotta hold the ball off.
Shane
How long ago was this?
Cheryl Underwood
Oh, how how long have I been on a sex senda wegovy and now I'm on zepbound. About three years.
Matt
Oh, nice.
Cheryl Underwood
Oh, look at, look at. You can see my weight fluctuating. That's why my book is called I'm fat because of you. So I'm writing my life story and it's called I'm fat because of you. Because I wanted to talk about the times that my body was protecting me and then it was attacking me and all the things that I was going through in life because I was like. I was a slim goodie back when I was in sexual interpretive dance. What?
Matt
You were a slim goodie back when you were in sexually?
Cheryl Underwood
That's what we call be in academia.
Matt
Nate did sexually interpretive dance to sexy Red Dude.
Cheryl Underwood
Now that's what they can say you do. Let's get out and do sexual interpretive dance. Yes. When I. I was much smaller, but then I think stress.
Matt
You were a stripper?
Cheryl Underwood
I attempted to. Back then it was called lingerie modeling. And I was in college and I answered an ad to model. You modeled a lingerie? And then the guys. It was in a bar tavern type situation. It's not a trick. No, it's a true story.
Matt
No, no, I mean a trick. This is to get girls to.
Cheryl Underwood
No, uh, you go in, we put on the lingerie, we model it, and the guy who buys it, you're supposed to strip it off for him.
Shane
What?
Cheryl Underwood
You know, but God lets you know what you can't do. And I wasn't good at it. So I was doing all the Fred sampling. I was making people laugh. You know, when Hood do that, you funny. You need to put your clothes on to go home, but you funny.
Matt
That's awesome. You know. So you went to school in Chicago.
Cheryl Underwood
I went to Fresno City College. That's where my associates is from in Fresno, California. My bachelor's is from University of Illinois, Chicago. My master's degree is from Governor State University Park, Illinois. I have five honorary doctorates, four of them from HBCUs and one of them from my own alma mater, UIC.
Matt
That's great. That's awesome.
Cheryl Underwood
Yeah. So my doctor, five times. Yeah.
Matt
That's crazy.
Cheryl Underwood
And I want to go to college and. But I also want to be in the entertainment business. You know, I want to be smart enough to sit across from my lawyer and understand what was going on. Sit across from my accountant.
Matt
I don't know what they're saying.
Cheryl Underwood
Yeah, so you gotta know.
Matt
I don't.
Cheryl Underwood
You gotta.
Matt
They're gonna trick Me, they're just gonna.
Shane
Regalese is crazy.
Matt
No, I don't understand.
Cheryl Underwood
It's. All it is, is Latin. It's Latin. All you gotta do. I took Latin in college. But you need to. Okay, now you're gonna have to marry either a very smart, progressive black woman. You need a black wife. You need a.
Matt
He's got a black wife.
Cheryl Underwood
Your wife is black?
Shane
Yeah.
Matt
Yeah, she's from Chicago.
Cheryl Underwood
What's her name?
Shane
Brittany.
Cheryl Underwood
Britney. Hold on, let me ask some black people. What year do you think she was born? I don't know where you said Britney's born, but Brittany's Chicago black.
Matt
Like, just to defend me, is she
Cheryl Underwood
south side black or west side black? South side, south side black. What, What? What location?
Shane
Like Pullman, I guess.
Matt
Drop a pin.
Cheryl Underwood
Damn. So what's where? Pullman. Oh, she in the wild. Wild hundreds. Oh, yeah. Britney ain't no punk.
Matt
Matt visits and he jogs in the neighborhood you got. And they chase him. Looks like Rocky, he's running.
Shane
Discourage strongly from jogging.
Matt
Jogging?
Shane
But I don't know my job.
Cheryl Underwood
Either you're an insurance man or undercover cop. If you walking through the black neighborhood like that. And you in the wild, wild, hunted. Did you ever go to the Copper Box?
Shane
Was that okay?
Cheryl Underwood
And then Brittany didn't take it. She was like, stay your ass at home. So how'd y' all meet?
Shane
Tinder. We met online.
Cheryl Underwood
You lied?
Shane
Swear. And you fell into Philly? Yeah. She came to Philly for her master's degree and then we met on Tinder.
Cheryl Underwood
You have any children?
Shane
Two.
Cheryl Underwood
Wonderful. How old?
Shane
Six and three.
Cheryl Underwood
Wonderful.
Shane
Yeah.
Cheryl Underwood
How did you know she was her. I don't know.
Shane
I just figured it out. We moved in pretty quick. We, like, went on a second date. And I just, like, stayed at her house for pretty much then on Wonderful.
Matt
I mean, our house sucks. Yeah.
Shane
I was living with, like, six guys, so.
Matt
Yeah.
Cheryl Underwood
Oh. So, you know, it was like a bachelor pad.
Shane
Yeah.
Cheryl Underwood
And you fell in love and then y' all accelerated it. I'm very proud of you. Now, what's up with you?
Matt
Just.
Cheryl Underwood
I know this is supposed to be your interview, but.
Matt
No, this is how we.
Cheryl Underwood
So. So, okay. So what type of. I'm be nosy. What type of women do you, like, Describe her.
Matt
They usually are blonde.
Cheryl Underwood
Good.
Matt
Yeah.
Cheryl Underwood
Blonde and smart.
Matt
Not yet. Not yet.
Cheryl Underwood
Not that blonde women are not smart. I'm just saying. Do you like a woman who's smart?
Matt
It's tough to find.
Cheryl Underwood
What did Eddie Murphy say in Coming to America? My loins. Yeah. Do you want someone that you can engage in conversation.
Matt
Yeah, of course.
Cheryl Underwood
Right, right, right. Okay, now see, I don't understand. Like, I've been a widow since my. When my husband died. I have not been in what I consider a long term relationship because I can be quite reclusive. I like my alone time.
Matt
Yeah, I'm similar with that. Yeah.
Cheryl Underwood
I don't like to sit up with a man and watch sports with him because I'm not talking to him.
Matt
I'm okay with that.
Cheryl Underwood
Yeah, yeah. Oh, to tell you a story. So I had this dude I really, really liked and rarely I let people come around where I live, right? So he was like, so what you doing tonight? What you want to do tonight? He said, I want to watch the fight. I said, why don't you, you know, swing by? So I got the fight ready, right? I said, what you want to eat? And he text. I said, text me what you want to eat. So I got all the stuff he wanted and everything. And then on my side of the bed was a stack of newspapers and magazines. And on his side of the bed was everything he wanted to eat and everything. So he was like, so what you doing? I said, I'm shutting the fuck up so you can watch the fight. And he was like, so you don't want to talk?
Matt
That's wonderful.
Cheryl Underwood
Why the fuck am I talking to you? We gonna watch the fight. Fight.
Matt
This is great.
Cheryl Underwood
Yeah, it's. What?
Matt
And he. It didn't work. What's he.
Cheryl Underwood
No, it did, dumbass. He wanted to talk, but that's the. That's odd. I don't know why. Like if we're watching. Okay, what's your favorite team? I saw all the shirts and what's favorite team?
Matt
Well, it's Eagles and. Okay, no name football.
Cheryl Underwood
Okay, now Kyle, tell them. I watch college sports.
Matt
Yeah.
Cheryl Underwood
When I'm not. When I'm working, I watch enough of it. But when I'm not working.
Matt
Look, Saturdays, Saturdays for college football.
Cheryl Underwood
That's right. I don't know what the fuck I'm looking at. I just know I watch college sports.
Matt
Hold on a second.
Cheryl Underwood
I watch college sports and when I was drinking, I had my beer and my shit and my snacks.
Matt
Yeah, it's.
Cheryl Underwood
But nobody's there with me. Nobody's there with. Nobody's there. Nobody's there with me. I'm just watching sports. Now I will text Jim. Jim Kelly is my sports guru. Like when I watch Stanley cup stuff and I go, jim, my only question, how do they know where the hockey puck is? I can't see Shit.
Matt
Jim Kelly.
Cheryl Underwood
Not the. Not the football.
Matt
Okay.
Cheryl Underwood
If I was that cool, I was like, I have.
Matt
I have a fun story.
Cheryl Underwood
I would have told you that.
Matt
I got a fun story about Jim Kelly.
Cheryl Underwood
What?
Matt
So I had to do a. The super bowl, like two years ago. This. This guy, this rich guy asked me to go to this dinner and he wanted me to do stand up, but I was like, I don't know if I'm doing standup, but we just went to this like steak dinner at this. It was like a long table, but it was just NFL hall of Famers. So it was like for real, Everybody. I was sitting next to Jerry Rice. It was like, Jim Kelly, Shannon Sharp. It was. Oh, Nate was there. Nate twerked. But who you.
Cheryl Underwood
Who were you twerking for?
Matt
It was a different mean thing you did to me that it was.
Cheryl Underwood
You called me a pedophile.
Matt
Yeah, that's how I. Well, that's how I closed. So thankfully, Joe Jim Kelly led the table in prayer before.
Cheryl Underwood
Oh.
Matt
Because otherwise I had no material really. But it was just Jewish bankers and NFL hall of Famers.
Cheryl Underwood
But they have senses of humor. Jerry Rice. Jerry Rice is my fraternity brother. I'm a member of Zeta Phi Beta. He's a member of Phi Beta Sigma.
Matt
The only thing he laughed at was when I called Nate a pedophile.
Cheryl Underwood
Pedophiles. He probably thought that.
Matt
Then he lifted his head up and left.
Cheryl Underwood
And I'm sure you guys saw the. The club say Shay clip. Shay Shay interview I did with him.
Matt
No, I didn't see that.
Cheryl Underwood
Oh yeah. Shannon and I sat in a car for hours when he was playing in Denver. So I was in the Denver. I think it was when they first opened the first location of the improv. And what's the other guy? Is it Terrell Davis?
Matt
Yeah. Okay.
Cheryl Underwood
So I thought Terrell Davis was Shannon and Shannon was Terrell. So he was like, so what you want to do after this? I said, I'm sell these CDs. Back then I was in the CDs and cassette tapes and posters. So he was like, what do you want to do? I said, okay, I want to go on a carriage ride, right? Because I saw the horse outside. I want to go on a carriage ride. He said, come on, I'll take you. And this is Shannon talking to me, but I think it's Terrell. And so I go, okay, let me. Let me get this money right here. So he starts walking up these stairs of the club and goes, come on if you coming. I said, who the you talking to? I said, yeah, I'm not. These in here give a about you. He was like. I said. I was like. And I said, motherfucker, I'm already me, Right?
Matt
Yeah.
Cheryl Underwood
So anyway, come on if you.
Matt
Come on if you're coming.
Cheryl Underwood
It was sexy. I got off on it. When he said, come on, if you covered, I was like, oh. Then I was like, wait a minute, bitch. Stand up for yourself. So I pack up my stuff after. I said, because even the white girls was like, he's telling you to come on. I was like, bitch, get a backbone. Fuck are you talking about? So we get together, we get in the car, and we can't find the carriage, right? So we sitting in the car for hours talking about what type of relationship we could or could not have. And fast forward to Club Shay Shay, where we've ever talked about it side by side.
Matt
That's great.
Cheryl Underwood
I was definitely wanting to be a Mrs. Shannon Sharp, but it wasn't meant to be. And we all stay friends. Ooh.
Shane
This episode is brought to you by blinds.com.
Matt
you know my favorite Blinds Steve, Stevie
Shane
Wonders and Ray Charles.
Matt
Matt. That was hilarious. Matt. Matt, up top. Yes. You're the funniest.
Shane
Do you want to go full DIY with your blinds, or do you want to bring in a licensed and vetted pro? Yeah, dude with blinds. Don't even. Don't even mess around. It takes two seconds. The bro comes in. I. I can speak to that for sure. Every time I move into a new place, I always forget, you need to get your own blinds. So you get there, and all of a sudden, the first two weeks, I'm like, getting crushed, but I'm gonna get the light.
Matt
Well, unless you live with a girl. You put up a towel.
Shane
Yeah, yeah.
Matt
You put up dirty blankets and towels.
Shane
You do the crack house treatment. Yeah, no, you need it. You need a licensed professional. That. That's where we're. You know, we don't. You know, that's what we need. That's our riff. That's our second riff twice. All right, guys. Right now, blinds.com is giving our listeners an exclusive 50 off. When you spend 500 or more. Just use secret code or use code secret at checkout limited time offer rules and restrictions apply. See blinds.com for details. You know, that's awesome.
Cheryl Underwood
Yeah, that's what you would hope. I mean, every man I've been with, I'm still friends with. You know, I'm like, cool if they're alive, but, you know, I'm still. I'm still friends.
Matt
I left Those jokes there.
Cheryl Underwood
Yeah. You cannot tell. Can I tell you honestly? And that's what I've been doing in the interviews is telling people, listen, if they had not come with respect and said, these are the topics.
Matt
Yeah.
Cheryl Underwood
But I didn't know what was going to be said and I did not know that Tony was going to do the George Floyd joke.
Matt
Yeah.
Cheryl Underwood
But when he did it, like, I was over there, like, scribbling on paper and asking, God, send me. Send me the response. Send me the response. Like the response to you. Send me the response. But I don't want to be mean spirited. But with Tony and the George Floyd joke, my only feeling is if you don't have the right response, that blows up the room even further. You've set back the cause. So sometimes it's say less if you ain't got nothing good to cut his throat with. Figuratively about comedy.
Matt
Yeah.
Cheryl Underwood
Shut the up.
Matt
Yeah.
Cheryl Underwood
Because you're gonna make it worse, in my opinion. What do you think?
Matt
I agree. I think that's. I think he nailed it.
Cheryl Underwood
Yeah.
Matt
Yeah.
Shane
I feel like the. So especially with the, like, the late husband talk, it was like this deeply personal, like a tragedy. And the thing no one talks about is like, you know, that's like horrific to even think about. And to be up there and just like laughing and making a good joke. And to me, it's like a triumph where you're like, you rose above it. You made a big joke out of everything. No one ever talks about that. It's. I thought it was. I watched it. I was like, this is beautiful. And then you came up and I think Shane said a lot of your stuff was kind of like off the cuff the last minute. Not even on the teleprompter. I was like, that, like, really blew me away.
Matt
Yeah.
Shane
Because I was like, how do you do that? In that room? I would be glued to the teleprompter, sweating, reading it, and to be like, all right, I have my own notes I just formulated on a stage, on live tv, in front of an arena of people. I really was. I was like, this is amazing.
Cheryl Underwood
Faith in God. Yeah, Ask God. Send me the words. Feeling safe. Feeling like I'm not being attacked so I don't have to be defensive. I don't have to be thin skinned. And culturally, we crack jokes. When he died, we did. We cracked jokes. I had to call my father and go, can you come here and identify the body? I was like, why? I was like, cause you my daddy gone in there and look, go in there, you know, But. But in stress, sometimes humor equalizes stress. So for me, when I first got to the talk on cbs, one of the first jokes I told was this joke about my best friend, Peaches. Now I'm in Chicago. My husband dies, jumps off a building. My best friend Peaches tries to outcry me at my husband's funeral. And we're in a. What is it? Funeral Home, 71st and Halstead. And I'm sitting up front. And in my family, we don't. Because we from down south, and my father is conservative Southern, but we don't express emotion out. Out in public. But. So I'm sitting up front and we are just wailing. Coming back from the back of the room. And it's my best friend Peaches, and she's wailing and coming up, and she is showing out. Black people know she is showing out at my husband's funeral. Now her husband is sitting about four pews back.
Matt
I'm just thinking about my family. At a funeral, if one person showed out, they'd beat their ass. What are you doing?
Cheryl Underwood
Now? We all looking around like, who is that? And she's wailing. And so my father is nudging me, and I'm nudging him. I'm like, I don't know what she cried. So I walk up to her and I put my arms around her and I go, bitch, the fuck are you doing? And we laughing, but it looks like we're crying with each other. And I said, I'm gonna let you go. Cause your husband, Ivory Eugene Granberry, 4. Four pews back, watching you cry over my dead husband. I'm gonna let you go. He gonna you up when you get home.
Matt
Yeah.
Cheryl Underwood
And. But I couldn't say those words. And Julie Chan Moonves was the one who said, let's make it TV friendly, but let's put some words in it and get a little seasoning.
Matt
Very funny.
Cheryl Underwood
But it's. It's when you say culturally, sometimes humor is the thing. It's the most uncomfortable. Humor that really kind of. It kind of lessens the tension and the stress, wouldn't you say?
Matt
Yeah, absolutely.
Cheryl Underwood
Do you feel you've ever gone too far in something?
Matt
Yeah, yeah, for sure. But then you're like, you know, as soon as you do it in a club, as soon as you're wrong, you go, shit.
Cheryl Underwood
Well, well. But I mean, puns are supposed to get. Groans, scatological humor, shit jokes, you know, they make you giggle like a kid. You know, the analysis of humor is what I love. But if you dissect a joke so hard, it's like a frog. You got to kill it to dissect it. But to me, for the people who are upset and on social media, I feel like you have a right to be that, because now I get to talk about mental illness in men, and specifically black men, that men feel. I don't need therapy. I don't need this. I don't need that right in this society. But people say, well, how could you sit there? Or it was offensive. Well, don't be offended for me if I'm not offended, but be offended for your point of view, and you can have your point of view.
Matt
Yeah.
Cheryl Underwood
We're not saying you can't have it. Have it all on social media because most people trying to attempt to do stand up will never understand how it feels. It's. It's like the greatest sex in the world with a bunch of people.
Shane
You know, he was just trying to keep the high going.
Matt
Milwaukee. Milwaukee's Milwaukee.
Cheryl Underwood
$50. Now, what did you want to ask me? I'm sure y' all had some questions. What do you want to ask me?
Matt
Yeah.
Shane
Well, really, the. My one question was, like. And I kind of. You kind of answered. It was like, how did you kind of put together that ad hoc, like, response to everything that you said? You just kind of channeled God and just chilled out and relaxed. What do you. I. I guess this is a question I had too, when, like. Because I've always wondered this before. Like, you know, you suffered this personal tragedy. Was there part of you that worried, like, I can't be funny again after this? It was like, I always wonder that if I. If you fall some like. Or some, like, horrible tragedy happens to me, well, it just, like, destroyed my sense of humor, and I'll become, like, serious and sad all the time.
Cheryl Underwood
I felt like I had no choice.
Shane
Yeah.
Cheryl Underwood
For me to survive. That's why the book is I'm fat because of you. Because I had to survive. I had to find a way to pay my bills. I had to find a way to build a career. So I just looked at it as. And my father was like, don't. Why me? Why not you? Like, tragedy can't come to your door like it comes to anybody else's door. So the first thing I thought, what is funny about this? What is funny? A lot of people say, well, why would you make a joke about being raped? And after I was raped, I went to the stage with it because that's the place where I'm most comfortable in talking to people. Something you feel it could have used
Matt
that one in the roast.
Cheryl Underwood
Yeah, I thought you were. No, no, no, no. They told me. They told me that. That you guys might talk about me. I didn't know rapes.
Matt
I would, first of all, definitely not do that. This lady got raped. What a loser.
Cheryl Underwood
Yeah, but. I mean, come on.
Matt
Crazy.
Cheryl Underwood
But, But. But would you say that is what roasting is now? It's no longer you a hockey puck roasting. In y' all generation, in this time span of comedy, you hit really below the belt. And for me, I feel like the only thing you gotta deal with, you ain't gotta deal with me. Cause I'm your colleague. You gotta deal with the motherfuckers outside on behalf of what they mad about. Right? But to me, if you worry about that, you restrict yourself to great comedy, right? So for me, every tragedy in my life, I bring it to the stage so that it. I can show the audience, you can survive any tragedy if God let you open your eyes the next day. Okay? Survive it. Because we talking shit, you know, if. If some. One of your relatives at the hospital that you hate, and we all in the hospital room going, if we could just pull the plug on this motherfucker. You see? See how we all laugh?
Matt
Yeah.
Cheryl Underwood
That's. That's what. What humor does. Even though we know we not gonna do it, or one of us might, but the rest of us not. That's what humor is for. It's Gallo humor. It's Irish wakes. It's black funerals. It's funny. Black funeral. Hey, dig that up and check his pockets. Why?
Matt
Because he owed me $50.
Cheryl Underwood
That's. That's humor that gets you over tragedy.
Matt
I didn't know. I wasn't certain your husband, your late husband was black. And then when I. The type of. The way he died, I was like, this sounds like a. This is a very white guy thing to do.
Cheryl Underwood
Thing to do. Jump off a building.
Matt
Yeah.
Cheryl Underwood
How so? What do you mean? Because that takes courage.
Matt
No, no, I mean, it does. No, I'm not disrespecting him.
Cheryl Underwood
People argued me down when I talked about that. It certainly does in mental illness. It. Take it. I felt it took him great courage to be in such despair that he would do something that there's no way I. I could have done that.
Matt
No.
Cheryl Underwood
No way. But for that type of despair and that type of stress, and people say, well, you know, because I. I had some therapy and. And dealing with some things, but my thing is, I. I did not kill my husband, but I may have exacerbated his stress. And so now that comes through in my comedy and saying what type of companion I want to be to a man, because I've watched the man I love.
Matt
You weren't talking during the game, were you?
Cheryl Underwood
No.
Matt
All right.
Cheryl Underwood
Not at all. Not at all. Now that, that, that is one thing. Now, I might ask you a question in a movie theater, but I. I don't like to talk. No, that's great, because I talk for a living. Don't you have moments where you don't want to talk at all?
Matt
Yeah. And for the second I get off the road, I sit on that couch and don't talk for three days.
Cheryl Underwood
And women don't understand it, do it?
Matt
Well, they get mad at you.
Cheryl Underwood
That's where that joke come from. You are out doing whatever you doing. Your man is out doing whatever he's doing. And as soon as you come home, you want to talk to him. Give him a minute, let him shit, shower, and shade, and then let him get situated and give you a signal that conversation should come forth.
Shane
That'd be really nice.
Matt
That'd be so nice.
Cheryl Underwood
That's why I tell that joke. That's why I tell that joke.
Matt
It's literally just like you were talking to everybody else all weekend. I watched you.
Cheryl Underwood
Right?
Matt
It's like. Yeah, that's. It's my fucking job.
Cheryl Underwood
That's right.
Matt
But.
Cheryl Underwood
But I don't want to talk now.
Matt
They don't hear that.
Cheryl Underwood
But. But then. Is that why you're single kind of.
Matt
Yeah, that's one of the reasons.
Shane
Yeah.
Cheryl Underwood
Is you. Do you. When you. When you finish the show, how do you feel about. Because stand up comedy is the most sexually attractive thing to do aligned with singing.
Matt
You gotta do stand up.
Cheryl Underwood
No, it is. It's a sexual. To make a woman laugh or to make a man laugh. It's a sexual thing. That's why it's so powerful.
Shane
I'm making a lot of guys, making
Matt
all these guys laugh.
Cheryl Underwood
Well, not that guy right there.
Shane
Yeah,
Cheryl Underwood
that guy. That's why he's happy. That's why he comes to work every day. All right.
Shane
I like that. I'll never stop thinking about that.
Cheryl Underwood
Right? But then when you. When you. You stop doing it, when the show is over, what do you do with all that adrenaline?
Matt
I drink.
Cheryl Underwood
Okay. I used to. It's not like I will never drink again, but I really want to see how I can reset my body for longevity. But I will tell you this. I drink because I like the taste of alcohol. And it's not that I like what it does to me. I like the taste of good whiskey or the taste of good gin or the taste of a great martini, you know? And I used to smoke cigars, but I don't anymore, but I like that sort of thing. But are you drinking because your adrenaline is up and now you need to pump the brakes because alcohol is a depressant? Or do you drink because you like to taste the alcohol?
Matt
I like drinking.
Cheryl Underwood
Right. And you drink by yourself. No, you drink with bitches. I mean, women.
Matt
No, it's almost entirely men. You should see my green room. It's literally why you don't slip to
Cheryl Underwood
Mickey and then get what you want. Cause I see you looking at him. Slipped to Mickey to drink. And then, you know, finally, I got Shane where I want him. Got your hat turned back.
Matt
Y.
Cheryl Underwood
Got your socks off. Get him.
Matt
Bad boy.
Shane
He a bad boy for life.
Cheryl Underwood
Get him.
Matt
Takes over the whole. Usually just guys.
Cheryl Underwood
Well, see, but that. That's the. That's the wind down. Yeah, right. It's the wind down. And we remember. We would go. We used to have this thing and everybody goes to it. It's called the company field trip. And the company field trip is where I would take my entire team to the strip club and we would. I would bring in.
Matt
We should have a company field trip sometime.
Cheryl Underwood
You'd love it. You'd love it. It's a lot of fun, a lot of great food. Where are we going? Magic City. Magic City in Atlanta. The wings are amazing.
Matt
Wings are good.
Cheryl Underwood
The broccoli.
Matt
I fucking grubhub them.
Cheryl Underwood
Yeah.
Matt
I didn't even go to Magic City. I got fucking lemon pepper wings. To my. The wings and the broccoli.
Cheryl Underwood
Yeah, Wings and the broccoli. And the service is amazing. And we would go in there and people would say, well, Cheryl, why do you go into strip clubs? 1. To talk to the girls about. Listen, I came last year.
Matt
I like to talk to them, too.
Cheryl Underwood
That's right. Your aunt's still here.
Matt
Yeah.
Cheryl Underwood
You said you were doing this for beauty school. Why the fuck you still here? Or college or whatever. But then also, it's the only place where the guys aren't looking at me. They're talking to me about politics and sports and current events or street life. They're not looking at me. They're talking to me. They're looking at her. And then she primes them up. And then I just lean over and go, so what you doing after this?
Shane
It's kind of genius, honestly. Yeah, it's funny. It takes like 12 naked tits to just focus on conversation.
Matt
Sitting next to her, just like. So how have you been?
Cheryl Underwood
Yeah.
Matt
I never even asked. What's going on with you?
Cheryl Underwood
How's little Tay Tay doing? How the kids? Yes.
Matt
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Shane
My eyes light up when I think about staffing personnel.
Matt
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Shane
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Matt
Me?
Shane
Yeah.
Matt
Who me thinking Lincoln. I got. Yeah, just the stinking Lincoln. July 17th. Please come to Lincoln Financial Field in Philadelphia. It's the most important moment of my life.
Shane
Yeah, that'll be fucking nasty.
Matt
And if it doesn't go well, I'm going to leave this earth. I'm gonna get pyro underneath the stage and I'm gonna tell them, go ahead. Yeah, just send it. Flame me. I'm out,
Shane
guys. I picked up some comedy club dates. All summer long. We're going to be having fun together I'll be six, five. June 5th and 6th, I'll be at the Summit City Comedy Club, Fort Wayne, Indiana. And that is. That's in just a few weeks.
Matt
I ran into a buzz saw over there.
Shane
Did you really?
Matt
Yeah.
Shane
Would you. What happened? Just an absolute negative experience.
Matt
People were just hammered. It's a fun club.
Shane
Yeah, that'll be. I'll be there in the dog days of the summer. Levity Live, Huntsville, Alabama, the Stardome Comedy Club, Birmingham. I'm excited for that. And Spokane Comedy Club, Spokane, Washington also. It's not up yet, but I have a bunch of more dates, so check them out on mikosco.com.
Matt
goodbye.
Cheryl Underwood
What else you want to know?
Shane
How do you wind down now after the show? That's something I always struggle with. How do you like? Because I feel crazy. I just.
Matt
How did you not drink after the roast? That was fun.
Cheryl Underwood
I kept telling myself, you don't want to. I got a goal that I'm trying to get to.
Matt
Sure.
Cheryl Underwood
I can tell myself, stay focused. It's like being an athlete. Most people don't look at us as athletes because it's such a sedentary life and you know, it's excess. Right. But being a stand up comic, you have to be able to remember what you're doing, then remember what when it doesn't work to replace it with another joke. And you have to be ready to. If I've been drinking all night now I'm puffy on camera. Right. So it's a, it's a lot of regimental type training. But for me, after the roast, I just felt relieved. That's first thing. Wanted to get out of my shoes. But also, I normally don't go to after parties. I don't hang out. Rarely do I go to what they call Hollywood parties because I'm kind of reclusive. But then I thought, come on, Cheryl, you need to engage because you need, you need work. I need work. Especially there's no TV shows, no movies being done. I was on daytime TV for 14 years. So for me, I thought, okay, do this. And then I wouldn't. Never got representation and the things that happened so fast after that. But also I wanted to enjoy the high of the. Working with my colleagues. That's what I want. To experience it without alcohol in my system. So I can remember it. Why you smiling?
Matt
I just, I had a great time. Yeah, I was fucked up.
Cheryl Underwood
Yeah.
Matt
I love my colleagues. Made me love them even more.
Cheryl Underwood
When you walked up to me with the Bud Light in hand. I said, that's the guy. That's the guy. And I thought that was the coolest thing. But the. The chance that we talked backstage and. But then also to have a 45, 30 minute conversation with the Rock about life.
Matt
Okay.
Cheryl Underwood
How'd you feel?
Matt
I've. I've met him before and he's the nicest.
Cheryl Underwood
Yes.
Matt
It's crazy how nice he is.
Cheryl Underwood
Yeah.
Matt
Yes.
Cheryl Underwood
Yes.
Matt
When he was making fun of me, he was talking about me and him working out together and then sitting in a sauna. And it was true. We really did that.
Cheryl Underwood
Yeah.
Matt
And me and him were in a sauna and he was just the coolest.
Cheryl Underwood
Yeah.
Matt
Yes. Nicest. It was weird.
Cheryl Underwood
Yeah, it was.
Matt
You know, and having our body types sitting across from each other.
Cheryl Underwood
From each other. And you. Okay, but would you work out with him?
Matt
And would I or did I.
Cheryl Underwood
Would you On a consistent basis?
Matt
No, no.
Cheryl Underwood
Mark Wahlberg, would you work out with him?
Matt
No.
Cheryl Underwood
He's a really good three in the morning, but he's a really great person.
Matt
I've never met spiritual. Yeah.
Cheryl Underwood
There's a photograph. The Pacquiao Mayweather fight. There's a photograph of me and Mark Wahlberg on a. Like this. Some kind of landing. And we're just really ragging on Jake Gyllenhaal while he's being interviewed. And he's a really good dude, spiritually. Good.
Matt
Good Catholic.
Cheryl Underwood
Yeah. Anybody understands his humanness?
Matt
Yeah.
Cheryl Underwood
You know, that's one good thing about being in the entertainment business. You come across people you see in TV and movies and you get to talk to them and you'll find out the good or the bad and go you a trip or. I'm glad you.
Matt
I've met too many bad ones.
Cheryl Underwood
Really.
Matt
Not yet.
Cheryl Underwood
Of. Of those that are not. You want to name them?
Matt
No, I don't think I've really met any.
Cheryl Underwood
Yeah. Rarely do I get my.
Matt
You feel pretty cool.
Cheryl Underwood
Yeah.
Matt
Yeah.
Cheryl Underwood
Same way. But that has. Speaks more to who. Who you guys are than who the person is, you know, because you're not gonna track too much. You got hands, Shane.
Matt
It's been a while.
Cheryl Underwood
You put your beer down.
Matt
As soon as you put your beer, miss a punch and fall down. Pants fall down.
Cheryl Underwood
That one. I gotta step up and throw these little hands for you.
Matt
That's why I keep my. My squad.
Cheryl Underwood
You see big baby, that big baby over there.
Matt
That big baby, big baby.
Cheryl Underwood
That's cuddly do, right? Right there. That's cuddly do, right?
Shane
He just squeal. Squeeze. Somebody just get in there and squeeze it.
Matt
Our whole squad's drunk. We would. We would lose to almost everybody.
Cheryl Underwood
So.
Shane
Yeah.
Cheryl Underwood
So your lover's not fighters.
Matt
No, we try. We try to fight.
Cheryl Underwood
Try to fight. But you. It's a swing and a miss, ladies and gentlemen. But I would say I was. I would go around, went to the after party, but I was like, come on, Kyle, let's get in the car. Why? Because it's time to go.
Matt
Yeah.
Cheryl Underwood
You know, even doing Tony's podcast last night, and then people go, there's a party after.
Matt
Oh, yeah, yeah.
Cheryl Underwood
Oh, yeah. And I was like, hey, let me. Let me do my thank yous and thank you for having me. And, you know, you get to a stage in your career where you like, yeah, this is wonderful. You kids have fun. Go to bed. Turn the lights out. Make sure you put the humidifier.
Matt
I did leave that after party early. After the roast, I left. Yeah.
Cheryl Underwood
Really?
Matt
Yeah. But then I was walking out, and there was tmz. Yes, they got me.
Shane
Well, they were trying to find.
Matt
I was trying to find Lewis. Our one friend was. I don't think he'll mind. He was on Molly.
Shane
I think, oh, yeah, he doesn't care.
Matt
And I walked out, and TMZ was out there, and they're like, what's up, man? How do you think that went, huh? And I was like, I'm trying to find my Mexican friend. He's on drugs. And they're like, followed me around the corner, and Lewis was sitting there like. I was like, this is him. Because right when I walked out the door, guy was like, there's a guy named Lewis who says he's with you, and he keeps bothering us. You got to get him the. Out of here. I was like, damn. Then TMZ was like, what's up, dude?
Shane
That's. How do they not air that? That's a great.
Matt
I don't know. I hope they have it. That's a great interview.
Cheryl Underwood
How often do you come to la?
Matt
Never.
Cheryl Underwood
Really?
Matt
Yeah.
Cheryl Underwood
Why? You don't like it?
Matt
I. I only really go places for shows to do shows. So once a year, Twice a year. Really? Yeah.
Cheryl Underwood
See, I. I look at LA as a. It's a. It's a small country town with a lot of big, inflated people. You know, it's. It's really. Everybody knows everybody.
Matt
That's true.
Cheryl Underwood
It's smaller than people think. It just appears big because it's, you know, Beverly Hills, Hollywood, Century City. But if you actually get in it, you're like, oh, you just. Like regular people. You just have maybe a lot of money or A lot of power.
Matt
Yeah, I never go to la.
Shane
Yeah, I like la. Started out as a puritanical religious community. Funny enough. Movie industry came in and they were like, maybe not.
Cheryl Underwood
Yep. Yeah.
Shane
I like California in general. I just like the.
Matt
It is awesome.
Shane
Yeah, it's nice.
Cheryl Underwood
You know what you would really love?
Matt
What's that?
Cheryl Underwood
San Joaquin Valley. It feels like the south. It's a lot of farmland. When I went to high school, I went to Atwater High Castle Air Force Base. We had Aggies, and so the Aggies are kind of like the country and the cowboys and stuff like that.
Matt
That's nice.
Cheryl Underwood
Yeah, you would. You would really like it.
Matt
Yeah.
Cheryl Underwood
You would like it a lot. A lot of drinking.
Matt
I like drinking.
Cheryl Underwood
A lot of.
Matt
I like looking at farms.
Shane
Yeah.
Matt
Not working.
Cheryl Underwood
There you go.
Matt
Yeah, yeah, yeah.
Shane
You gotta go to Napa. Napa's nice. You just go this week, get hammered on farms.
Matt
I was supposed to go there this weekend.
Cheryl Underwood
Why?
Shane
You know what happened?
Matt
I was. I'm tired. True. I didn't want to go. It was like a music festival.
Shane
Yeah, yeah, yeah. You wouldn't feel good afterwards.
Cheryl Underwood
No. Yeah.
Shane
Get hammered. So what's. What's the plan, then? So you said after the roast, it was just. Things kind of connected and took off. What's. What's the plan outside of the special?
Cheryl Underwood
And I would say continuing to work on the road, because I love working on Ro. Me and Kai on I Need a Job Tour. That's why we named it that, because like most Americans, we need work. You know, I want to get deeper into podcasting.
Shane
I was just about to say, do you have, like, an interview show you do or anything?
Cheryl Underwood
Well, Kyle and I are working on Politics and Punchlines as the podcast because I want to be able to talk about the politics of all situations, including politics. And the punchline is the humorous thing that comes out of that discussion. And move on to interviewing people. I want to start with just me and Kyle, because you can't depend on the interview, because the interview either might not show up or might not be good.
Shane
Yeah.
Cheryl Underwood
If you guys aren't good together, your chemistry, then you don't have a show. So I want to get into podcasting. I want to go back to terrestrial radio.
Shane
Nice.
Cheryl Underwood
I believe in radio, even if I'm just a contributor in all formats. Cheryl Underwood's Great American Talent Search. We're doing the first one in Lake Charles, Louisiana, and I believe that.
Matt
What kind of talent?
Cheryl Underwood
It's everything.
Matt
Everything.
Cheryl Underwood
Spoons.
Matt
Someone's gonna. Someone's gonna play the spoons.
Cheryl Underwood
Washboard. If you do hair and you can put in a quick weave in 60 seconds, that's your talent. If your dog jumped through a hoop or if it bark and sound like it's singing, that's a talent. You can do a monologue. But if you are a singer or a singing group or a band, you must master the past. That's classic rock, classic country, classic R and B, classic soul, classic gospel, classic Latin, whatever you do.
Matt
Yeah, classic hip hop.
Cheryl Underwood
Yes, classic hip hop.
Matt
Guys up there like, hey, everybody, my name is Jim.
Cheryl Underwood
Yes, yes, yes. Because what it does, it brings in the demographic that remembered all that music, right? If somebody gets up and does Ronnie Millsack, wouldn't it be great if a white dude got up and was singing some type of country song, maybe even a George Jones song, but then said to the audience, let me show you what else I can do, and then start singing Keith Sweat.
Shane
It'd be wonderful, wouldn't it? And I come out and have my dog jump through a hoop. And I'm like, hey, everyone.
Cheryl Underwood
Okay, so wait a minute.
Matt
Some guy with a fucking pair of spoons is sitting backstage going, oh, oh, I gotta follow that.
Cheryl Underwood
That's it.
Matt
Wait a minute.
Cheryl Underwood
So would you guys help me pull it together?
Matt
Matt would. We'll perform.
Shane
Yeah.
Cheryl Underwood
Really?
Shane
I like play music.
Cheryl Underwood
Yeah. All but it's anybody doing anything.
Matt
He's got a blind dog.
Cheryl Underwood
There you go. I blind dog playing the spoons. It's hilarious. You can't beat that kind of talent. Benji
Shane
does sound nice though. Yeah, I like the multi genre. Like let's. Let's see it all. Let's see what you can do.
Cheryl Underwood
But it crosses the reason I want to engage radio with it. It crosses all formats and I want to do the preliminary rounds through comedy clubs. So it's a really an elevated version of the open mic hosted by local comedians and local radio jacks. And then when you get to the final round, then that's where you really have. It's a bigger experience for the community. It brings in small businesses, it brings in corporations, but it brings the community together. If your fire department got up and did new addition, it would really be a great experience for that. But the one we're doing in Lake Charles is doing Juneteenth and I asked them, while we're tabulating the results, could we do a reenactment of Juneteenth?
Matt
I'll be a part of that.
Shane
Yeah.
Cheryl Underwood
Now what would you be wearing, Blue or gray?
Matt
Blue. Come on, you see the house.
Cheryl Underwood
I know. I just want you to say it for the people. Right. But don't you think. See, to me, that's what brings us together. Right. And to do something fun like that. After we do the I Need a Job tour, my next tour will be Sherlon Woods. Great American talent search.
Matt
Oh, man, I was gonna make a terrible joke.
Cheryl Underwood
Okay. Reggae.
Matt
You know what the, the guys did after Juneteenth? What? They, they went on the I Need a Job tour. They said, oh, I need to go on tour.
Cheryl Underwood
Listen to me, listen to me. For the brothers and sisters that's watching. He means the Fisk Jubilee Singers. Okay, so we got you on camera. You going, you going to help me pull this together?
Shane
Yeah.
Cheryl Underwood
Because I think it'd be great for the country and you can find talent. And if you want to put Afrobeat or, or EDM underneath some classics, you got to do something. I just think we can find the next Sticks or Boston or even Leonard Skynyrd.
Matt
Yeah.
Cheryl Underwood
I think because all of that, these kids do not understand the fun we had in forming a group or making a band or, you know, trying to make this music or this and coming together, you know, as entertainers. How could Michael Jackson be vilified, die, and then become the best selling movie, but all his music is going back up the charts if there isn't something there. Right?
Matt
Yeah.
Cheryl Underwood
And so for me, I just want to bring the country together and I believe in this as something that would bring us together and could possibly turn into something really, really great.
Matt
That's awesome. That'd be nice.
Cheryl Underwood
Yep. What else you want to know? Is it time for me to go? Let me look at. Oh, look at the time. Yeah, that's another thing too, that I have a tendency to do. I could be with a man and I feel like I'm getting a little too relaxed, a little too talkative, and I go, you know, I think I need to go to the bathroom and then I'll just sneak out of the building.
Matt
That'd be, that'd be so confusing. I was like, things were going well and she left.
Cheryl Underwood
No, no, I, I. Once these phones came out, yeah, I will text her from the car and go, hey, call me later. Or I'm gonna call you when I get home. That stops the, oh, she left. No, she really likes me. But I snuck out.
Matt
I still would be like, I also think I scared her.
Cheryl Underwood
Scared of what?
Matt
If a lady escaped.
Shane
Yeah.
Matt
Well, if she left the house without
Cheryl Underwood
saying if I'm lingering. My dad had a saying.
Matt
A saying, that's nice.
Cheryl Underwood
Ling along, but die you must. I don't want to linger. That's a country's hell. Don't we from Arkansas? Yeah, we from Arkansas. So to me, yeah. He said, ling along, but die you must. That's right. Time I make a monkey eat red pepper. You know, he had these great Southern things. Think about that.
Matt
That's nice.
Cheryl Underwood
That's right.
Matt
It's tough for me to figure out, but I like it.
Cheryl Underwood
Yeah. Yeah. Chicken ain't number the bird and bush ain't number chewed up grass. That was my dad. Right. So to me, if I'm. If I feel I'm lingering, I will make a getaway, you know?
Matt
Yeah. Lingering after you hook up or. Cause that's a great time. If a lady escaped after that, I'd be like, that's one.
Cheryl Underwood
Clinginess is a problem.
Matt
Yeah.
Cheryl Underwood
Yeah. To me, I kind of resist. Maybe I'm. You think I'm commitment fold when you say fellas on my team, I'm a commitment fold.
Shane
Possibly.
Cheryl Underwood
Well, listen, I believe in love. I believe in monogamy. I'd like to get married another time, but I believe marriage is till death do us part. I talk about it in my show, but I want to go through the courtship. Like, I believe you should not live with a man in house. And I could be married to a guy and not live in a house until we're ready to live together, because that's what fucks up the relationship, in my opinion. When you rush cohabitation and you're not ready. So for me, like, if I, back in my one and done days, sleep with a guy, I would, like, wait for him to go to sleep, and I would just borrow my clothes up and sneak out the hotel.
Matt
It's. It's wonderful. But nothing better than waking up and be like, oh, nice.
Cheryl Underwood
And if I'm at his house.
Matt
Yeah.
Cheryl Underwood
I would sneak out the house and put my car in reverse and let it coast out so the car wouldn't start.
Matt
That's another one where I'm starting to get worried.
Cheryl Underwood
No, no, because. Hey, Kyle, do you remember that time that I put the young handsome man basketball dude? Yep.
Matt
From the front row.
Cheryl Underwood
And then what did I do? Didn't I call you? And I said.
Matt
And I was like, why are you whispering?
Cheryl Underwood
I said, shh.
Matt
I was like, oh, oh, oh.
Cheryl Underwood
I said, come get the luggage. And you was like, why you whisper, come get the luggage. And don't let the elevator ding because I'm right next to the elevator. Because I didn't want to see that pitiful look in Your face when the woman leaves. I was like,
Matt
you know that pitiful face is fake, right? You know that's fake.
Cheryl Underwood
Now something looking sad. Oh, don't leave something look sad. They look. Why are you leaving? No, that's fine. I thought we were gonna go get something to eat after. No, no, no. I like my life.
Matt
That's good.
Cheryl Underwood
Nah, we see we should do with a dating show.
Matt
I rarely talk about it, but.
Cheryl Underwood
Yeah, but you know, because I think women need to hear what men really feel.
Shane
Yeah.
Matt
Nothing.
Cheryl Underwood
Nothing. See, I think y' all do feel something. Y' all just don't believe that women are going to listen. She's stupid.
Matt
But yeah, Also, you can't be vulnerable to a lady. She'll hold it against you forever.
Cheryl Underwood
That's not the right girl.
Matt
I saw you cry. You okay?
Cheryl Underwood
Okay. What sporting event did you cry at?
Matt
So many. So many.
Cheryl Underwood
Thank you. Yeah, that's right.
Matt
Oh, who gets the scholarship to walk on? Oh, that's every time. It's over. Down syndrome. Guys hitting threes.
Cheryl Underwood
Yeah, it makes you cry. It makes you. It makes you cry.
Matt
Putting a guy in. Yeah. Special needs guy on the bench. Comes in, hits a couple threes. That's beautiful. Yeah, yeah, yeah.
Cheryl Underwood
So why can't you cry in that?
Matt
I could. Yeah.
Cheryl Underwood
Even to one tier.
Matt
That's nice. Yeah. I'm okay with that.
Cheryl Underwood
If she's smart, she won't rag you for it. She'll understand. He does have humanity. Yeah, but. Shut the fuck up. Sometimes you ain't got to say everything to this dude. Just notice everything.
Shane
That'd be nice.
Matt
Yeah. Yeah.
Shane
I feel. I feel a lot. I feel a lot of feedback myself.
Matt
Yeah, you get some feedback.
Shane
A lot of feedback.
Cheryl Underwood
Really? Yeah. See, I just don't think. I don't think we need to talk about everything. You know, sometimes when a man is ready to talk to you, be ready to listen. And sometimes don't answer back. Just. Just listen to them and not go, yeah, wonderful. I got it. Or sometimes I'll say, are you. Are you cool? Are we cool? Are we still together? Yeah, Are you cool?
Shane
I feel like you need some time behind you before you can eat the proverbial pepper of just not bothering a guy that hard.
Cheryl Underwood
Time plus distance equals clarity. Yes. I'm going to leave you alone so that I don't shoot you. Right? I'm gonna let you have your space. Cause you talking to me crazy. You know you kind of flagrant right now. I know you mad about some bullshit. I didn't know that was your father. Motherfucker why is you in my face? Just listening. You listen to a guy also. Figure out what he eats. Figure out what his comfort zone is. Make that great, because then he's gonna make everything great for you.
Shane
100%.
Cheryl Underwood
Happy home. Peace of mind makes a man.
Shane
It's true.
Cheryl Underwood
That's right.
Matt
Me and Lamar live together.
Cheryl Underwood
So will you find the man of your dreams?
Matt
That's me. He won't. He doesn't make me anything. Lemaire hasn't cooked once, actually. He made chicken Alfredo. That was nice.
Cheryl Underwood
Get some chicken.
Matt
There's chicken curry in there from a week ago. That's in that jug in there. Throw that out. That's been disgusting. Come on. He's got a jug of chicken curry in there. It's gross. I didn't know where to put it. Throw it out. Throw it out. But how we doing? That's. That's good.
Shane
Yeah.
Matt
All right. Thank you very much, Joe.
Cheryl Underwood
Thank you for having me. It was. Thank you.
Shane
I was stoked when I heard you were coming on.
Matt
I was like, this is awesome.
Cheryl Underwood
Yeah. Look for. Look forward to working with you guys. Let's. Let's work together to truly bring the country together.
Matt
I would love that.
Shane
Let's do it.
Cheryl Underwood
I would, too.
Matt
Good stuff.
Shane
Watch new episodes of Matt and Shane's Secret podcast on Spotify. Do.
Cheryl Underwood
You.
In this lively, uncensored episode, comedians Matt McCusker and Shane Gillis welcome the legendary Sheryl Underwood for a sprawling conversation about comedy, life after tragedy, relationships, working in entertainment, and the power of humor to address even the darkest subjects. Sheryl shares war stories from her time on the road and the roast circuit, gets candid about her personal life, and brings her signature blend of laughter, wisdom, and real talk.
"Everybody work with crew, keep confidences. Don't talk too much." (00:04)
“The second they unionize, they're dead.” (00:30)
“It's difficult for a man to come see a woman… It's an hour and a half of 'men ain’t shit.' What man wants to do that?” (02:48)
“He tried to find an orgy, took an Uber to a hotel, and they just stole $50 from him.” (06:00)
“You’re not gonna agree. You're not gonna like every joke I tell…let everybody else around you enjoy it.” (13:04)
"I told Jamie [Foxx], ‘I'm gonna bomb... I'm about to do some pro American jokes and pro president jokes.’” (10:18)
“These are the topics…but I didn't know what was going to be said and I did not know that Tony was going to do the George Floyd joke…You gotta have the right response, that blows up the room even further." (30:17)
“Every tragedy in my life, I bring it to the stage so that…I can show the audience, you can survive any tragedy if God lets you open your eyes the next day.” (37:04)
“Give him a minute, let him shit, shower, and shave, and then…give you a signal that conversation should come forth.” (40:07)
“You should see my green room. It's literally—” (42:21)
“Down syndrome guys hitting threes…that’s beautiful.” (64:50)
This episode exemplifies Matt and Shane’s signature style: freewheeling, brutally honest, and always hilarious, with Sheryl Underwood providing both the comic spark and heartfelt commentary. For listeners, it’s a look into the mechanics of contemporary stand-up, the lives behind the jokes, and the rare resilience of comedians who use humor to survive—and connect us all.