Club Shay Shay - Bert Kreischer Part 1

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What sparked Bert Kreischer's journey to becoming a comedian?

Bert Kreischer 0:00

One of the best days of my life was when Cat Williams knew who I was. Cat walks up to me and goes, you a goddamn rock star, Bert Kreischer. I've been trying to take my shirt off for years. They won't even let me wear a vest.

Unknown 0:12

All my life, been grinding all my life. Sacrifice, hustle, pay the price. Wanna slice, got the roll of dice That's why, all my life, I be grindin' all my life All my life, been grindin' all my life Sacrifice, hustle pay the price Wanna slice, got the roll of dice That's why, all my life, I be grindin' all my life

Shannon Sharpe 0:36

Hello, welcome to another episode of Club Che Che. I am your host, Shannon Sharpe. I'm also a proprietor of Club Che Che. Stopping by for a conversation and a drink today is one of the best storytellers of his generations, one of the top grossing stand-up comics in the business. He's performed at sold-out arenas around the globe, a world-renowned podcaster, a powerhouse entrepreneur who's built a media empire, a celebrated movie star, producer, actor, writer, host, content creator, a husband and a dad, and... He's a Florida State alum, one of the greatest partiers of all time, the machine, Bert Kreischer.

Bert Kreischer 1:09

Bert. Thank you. Thank you. Is that you? That's you? It doesn't sound, when you read it, I was like, gotta be somebody else. Yeah, that sounds like a lot, but yeah.

Shannon Sharpe 1:18

Tell us about this one, because you walked in, he's like, hold on, who? I got a stylist now, I gave you a price point. This is not the price point that we agreed upon. Who in the hell signed off on this?

Bert Kreischer 1:30

You get a stylist and I didn't know that you're paying for these clothes. They bring in clothes and they line them up and they're like, put it on. You like it. And I got tactile issues, so feel that. That's so nice. And then today I put it on and the price tag's on and I went, who paid for this?

How did Bert's identity crisis affect his early career?

Bert Kreischer 1:49

This is like, I remember you could buy cars for this. Exactly. And then you wear it, and I'm going to wear it all the time. You're going to see me on every podcast. No, no, you can't do that. I'm going to wear this once?

Shannon Sharpe 1:59

Yeah, one time, one time. You're at the stage now, you get it now. Because of who you are, if you wear it again, people are like, man, I saw him with that on Club Shea Shea. You're like, I don't give a hell. I'm going to wear it on somebody else's podcast, too. Oh, my God. Yeah, I'm going to wear the shit out of this. Man, but thank you for coming on Club Shea Shea.

Bert Kreischer 2:18

Are we really drinking? Yeah, we got to go. Buddy, this is... This is my dream. I ran into you two Super Bowls ago. And right when you started Club Shay Shay, I was walking right by you. You forget how big grown men are until you see them in person. And I scared the shit out of you. I went, Club Shay Shay! And you went, huh? And I was like, oh, big fan. And you're like, okay. And you just kept walking right by. Cheers, brother.

Shannon Sharpe 2:39

Cheers to you.

Bert Kreischer 2:44

That's nice.

What role did Florida State play in Bert's life and career?

Shannon Sharpe 2:45

Is this you? Yeah, that's me. You live in L.A.? I do. So good, we gonna send you home with a bottle. Oh, okay. So let's talk about your new show on Netflix, Free Bird. Yeah. You have to change from who you naturally are. How hard was it for you? Or is it hard, or you can just jump in and out of characters?

Bert Kreischer 3:09

No, it's not, first of all, it's not hard for me because I only play one character when I act, and it's me. It's Bert. Yeah, I don't audition for anything. I create the project and I play it. Okay. In The Machine, my movie, I play Bert. Okay. And in this one, I play Bert. And they're all pulled... It's just like stand-up. It's pulled from my real-life experience. I've always had an identity crisis because I do have this moniker and this lifestyle that kind of precedes me of, like, I party, I take my shirt off, I get wild. But then I am also a dad and I'm, like, I'm a husband. And so... And... You know, when I was a young father, I was not successful. And we were one of the poor parents at the school. And you'd see parents that had, like, nice cars and nice watches.

Bert Kreischer 3:56

And they'd come in in a suit. And I was in gym shorts and a cut-off sweatshirt with flip-flops. And I always had this, like, I never fit in.

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Chapters

8 chapters

1 What sparked Bert Kreischer's journey to becoming a comedian? 0:00–1:49 2 How did Bert's identity crisis affect his early career? 1:49–2:45 3 What role did Florida State play in Bert's life and career? 2:45–4:05 4 How did Bert transition from partying to pursuing comedy? 4:05–5:41 5 What was the impact of the Rolling Stone article on Bert's life? 5:41–7:18 6 How did Bert's family dynamics influence his career choices? 7:18–9:02 7 What humorous stories does Bert share about his daughters? 9:02–10:40 8 How did Bert's relationship with Will Smith shape his career? 10:40–1:07:45

Speakers

3 identified

Bert Kreischer 53 min Shannon Sharpe 6 min Unknown

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Topics in this episode

Netflix 1 LeBron James 1 Ryan Reynolds 1 Will Smith 2 prize picks 1 Bert Kreischer 3 Shannon Sharpe 2 Florida State 1 Cat Williams 2 Club Shay Shay 1 The Machine 1 Free Bird 1

Source

Recorded21 Jan 2026

Publisheromnycontent.com ↗

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Show notes

Download the PrizePicks app today and use code SHANNON to get $50 in lineups after you play your first $5 lineup! https://prizepicks.onelink.me/LME0/SHANNON Bert Kreischer sits down for a wide-ranging conversation that traces his unlikely path from Florida State party legend to sold-out arena comic. A Florida State alumn, viral content creator, and self-described one of the greatest partiers of all time, Bert reflects on how his reputation—and work ethic—eventually turned into a full-blown comedy empire. Bert starts by talking about where the clothes Shannon Sharpe gave him ended up, then recalls running into Shannon two Super Bowls ago and admitting he was already a fan. He breaks down playing an exaggerated version of himself on stage and promotes his Netflix comedy series Free Bert, explaining how leaning into character became part of his success. The conversation turns personal as Bert opens up about being an unsuccessful young dad while surrounded by parents who seemed to have it all together. He discusses watching his friends get rich around the same time he did, questioning what kind of millionaire he wanted to be, and dealing with an identity crisis and survivor’s remorse as fame hit while others struggled. He explains how his podcast became awkward when people kept asking how he “made it.” Bert revisits his six-year run at Florida State, how a Rolling Stone article changed his life, and why Oprah asked to have him and his parents on her show. He explains why he stayed in college so long and how he began turning stories from his friends and daughters into stand-up material—including stealing a joke from his daughter that she later demanded he remove. He shares stories of his daughters touring with him alongside Mark Normand, Shane Gillis, Joey Diaz, and Sal Vulcano, their no-nonsense views on celebrities, and setting boundaries like refusing to curse before 16 or asking him to delete videos. Bert also laughs about answering phone calls on stage, including picking up when Shaq called him from the toilet. Bert talks about walking away from baseball to become a full-time party guy, the embarrassment of losing his virginity, and how National Lampoon: Van Wilder—starring Ryan Reynolds—was inspired by his life. He explains why he chose not to sue, his desire to meet Reynolds, and hopes of appearing in a future Deadpool. The episode also covers his dad funding his move to New York, tough love birthday advice, getting fired for taking his clothes off at work, meeting Will Smith, pitching movies, and getting career advice at a urinal. Bert revisits the viral Russian Mafia train-robbery story, advice from Joe Rogan, tension with Kevin Hart, thoughts on Katt Williams, legendary comedians like Patrice O’Neal and Ralphie May, financial mistakes, marriage without a prenup, and his experience at the Netflix Tom Brady Roast—all before circling back to Free Bert on Netflix.See omnystudio.com/listener for privacy information.

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