Club Shay Shay - Bert Kreischer Part 2

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What is the main topic discussed in this episode?

Bert Kreischer 0:00

Thank you for coming back. Part two is underway. When you were in college, one of your best stories that you told was being a part of the Russian mafia.

Unknown 0:08

Yeah.

What stories does Bert Kreischer share about his early life and college days?

Bert Kreischer 0:10

How did you come up with that?

Unknown 0:11

I did it. I don't know. Like when you talk about being on the Ravens, how did you come up with that? I did it. Yeah. I mean, I did it.

Bert Kreischer 0:23

So how did you get involved in that? Oh, let's top it off.

Unknown 0:28

What are we doing? Damn, bro. I love the pours you give. Jesus. What is this? This is really good. This is not, this is whiskey? This is a cognac. No, it's not.

How did Bert Kreischer's identity crisis affect his career in comedy?

Unknown 0:40

Yes, it is. I only had cognac one time in my life. Two times in my life. Yeah. Two times in my life. Yeah. One time, it was at the Russian Ballet with Igor the Gangster. It was all they sold was cognac. Yes. And I swear to God, and he gave it to me, and I love drinking. Yeah. I love, if there's something I don't want to do, drinking can get me through it. Right. And he brought us eight baby bottles of cognac for the Russian ballet. They normally do vodka though. It was all they had was cognac. And I took one sip and I almost threw up. The other time I had cognac was Louis the 15th. 13th. That guy too. And it was on my wedding honeymoon and it was with an Italian mafia guy. Yes. who took me and my wife, his wife Dawn, and my wife Leanne, to dinner at this very, we were on a private island, and he got Louis XIII.

Unknown 1:39

And I threw it up just outside the restaurant. And I love this.

Bert Kreischer 1:45

And I've never liked cognac in my life. This is mine. It's a BSOP.

What inspired Bert Kreischer's Netflix series 'Free Bert'?

Bert Kreischer 1:51

BSOP, Very Special Old Pale. Aged between four and six years. In order for it to be a cognac, it has to originate in the cognac region for at least two years. So this is a combination between a Petit Champagne and an Uniblanc grape. Each region have their grapes that have a specific taste. Oh, well. What you got, what you got?

Unknown 2:13

This is my vodka.

Bert Kreischer 2:17

Are you Russian?

Unknown 2:18

No. And we make it in Texas. That's all I know. Now this is my vodka.

Bert Kreischer 2:27

Is it a potato vodka?

Unknown 2:28

No. It's the other one. Yeah, it's our vodka. Take that. That's for you. Okay. But I'm enjoying this cognac. I can't switch to vodka. No, no, you can't.

Bert Kreischer 2:37

Because you'll definitely be throwing up.

Unknown 2:39

Yeah. Russian Mafia. So, in all honesty, like I said... Because you know when you tell the story, people don't believe you. No one believes any of my stories. The one that killed me the most, out of all of it... is like, and it's like the worst moniker you can get. First of all, I'm a storyteller, so my story has to be entertaining first, factual second. I can't, if you want to hear facts, that's called nonfiction. It's not what I do. I'm a storyteller. It's based in truth, but it's got to be funny. The one that killed me the hardest was the Tracy Morgan story, which is the best story I think ever, ever, ever. And it's the first time I met Tracy Morgan. And And I told that and drama arose around it, but Tracy heard it and he didn't remember it or didn't.

Unknown 3:32

And he said, that never happened.

What personal anecdotes does Bert share about his family and fatherhood?

Unknown 3:34

And that bummed me out so much. And then one day recently, I got a FaceTime from Tracy Morgan. And he was like, you know, I heard you have a story about me. I said, I do. He said, I'd like to hear that story. I was like, okay. And so I flew to New York.

Bert Kreischer 3:51

You couldn't tell him over FaceTime?

Unknown 3:53

No, listen. You want to hear a story, I'll apply to you. It was Tracy fucking Morgan. He's, dude, listen, goats are goats, right? Yes. No shade on any comic. Chris Rock has to understand this. He's a brilliant comic. He's the reason I got into stand-up. That Bring the Pain is the best special I've ever seen in my entire life to date. And I know that Chappelle's are just getting better. But, I mean, Bring the Pain. Tracy Morgan's on a different level. Tracy Morgan is funny 100% of the time and 100% of the things he does. He can make eating crackers funny. I watched a man eat Chick-fil-A, and he had me rolling. I mean, the guy is just, he is comedy incarnate. So the fact that I had any kind of beef or... Any tension with Tracy Morgan broke my heart.

Unknown 4:42

I'm such a fan of his. So when he says to me, I'd like to hear that story, I said, I'll fly to New York. I'll tell it to you.

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Chapters

8 chapters

1 What is the main topic discussed in this episode? 0:00–0:10 2 What stories does Bert Kreischer share about his early life and college days? 0:10–0:40 3 How did Bert Kreischer's identity crisis affect his career in comedy? 0:40–1:51 4 What inspired Bert Kreischer's Netflix series 'Free Bert'? 1:51–3:34 5 What personal anecdotes does Bert share about his family and fatherhood? 3:34–5:21 6 What lessons does Bert Kreischer learn from his financial mistakes? 5:21–10:19 7 How does Bert Kreischer navigate the challenges of fame and success? 10:19–12:30 8 What insights does Bert offer on the importance of storytelling in comedy? 12:30–1:06:46

Speakers

3 identified

Unknown 47 min Bert Kreischer 10 min Shannon Sharpe

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Topics in this episode

New York 2 Russia 2 Joe Rogan 1 Bill Burr 1 Kevin Hart 1 Bert Kreischer 4 Nikki Glaser 1 Ari Shaffir 1 Tracy Morgan 3 Cat Williams 2 Ralphie May 1

Source

Recorded21 Jan 2026

Publisheromnycontent.com ↗

Transcriptspeaker-named · 100+ languages

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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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