Bert Kreischer: Comedy, Drinking, Rogan, Segura, Churchill & Kim Jong Un | Lex Fridman Podcast #382
Lex Fridman (host), Bert Kreischer (guest)
In this episode of Lex Fridman Podcast, featuring Lex Fridman and Bert Kreischer, Bert Kreischer: Comedy, Drinking, Rogan, Segura, Churchill & Kim Jong Un | Lex Fridman Podcast #382 explores bert Kreischer on comedy, excess, friendship, trust, love, legacy Bert Kreischer and Lex Fridman dive into Bert’s philosophy of joy, his creative process in standup, and the role alcohol and partying play in his life and persona. They explore his admiration for figures like Hemingway, Churchill, Rogan, and Segura, and how those relationships shaped his career, trust issues, and growth. Bert talks candidly about marriage, parenting, betrayal, workaholism, and using humility and relentless self-promotion to build a unique comedy empire. Underneath the wild stories, the conversation is about finding what you love, letting it ‘kill you,’ and cultivating deep, loyal relationships along the way.
Bert Kreischer on comedy, excess, friendship, trust, love, legacy
Bert Kreischer and Lex Fridman dive into Bert’s philosophy of joy, his creative process in standup, and the role alcohol and partying play in his life and persona. They explore his admiration for figures like Hemingway, Churchill, Rogan, and Segura, and how those relationships shaped his career, trust issues, and growth. Bert talks candidly about marriage, parenting, betrayal, workaholism, and using humility and relentless self-promotion to build a unique comedy empire. Underneath the wild stories, the conversation is about finding what you love, letting it ‘kill you,’ and cultivating deep, loyal relationships along the way.
Key Takeaways
Honor the ‘first draft’ of your creativity before over-editing it.
Bert says his best jokes are often perfect the first time he tells them; when he tries to “razzle-dazzle” and expand them, they can lose their simplicity and power, and he ends up chasing the purity of that original version.
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Use humility as fuel to pursue what you actually want.
A harsh birthday call from his father—calling him a ‘tremendous piece of shit’ for not chasing his dreams—forced Bert to confront his lack of humility, take any job at a comedy club, and grind his way into standup and later The Comedy Store.
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Treat trust as sacred, but be willing to rebuild it carefully.
After multiple betrayals, including Ari Shaffir drugging him, Bert became guarded but chose to forgive when he believed intent wasn’t malicious, and he deliberately chose blind trust with Tom Segura rather than live in a world where he couldn’t trust his closest friend.
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Relentless experimentation beats perfectionism in building an audience.
He emphasizes ‘don’t be afraid to suck’ with promos: most bad content is simply ignored, while creative risks like dance lessons, marching bands, or filming pre-surgery promos have directly sold out tours and turned into viral moments.
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Work like a maniac at what you love, but recognize the cost.
Bert openly loves working nonstop—tours, films, podcasts, promos—but admits it cannibalizes real life, raises concern among friends like Rogan, and is pushing him to finally consider a break to rest, sober up, and just live off-camera for a bit.
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Partying can create real intimacy, not just recklessness.
He frames extreme drunkenness as a kind of vulnerable ‘gift’—letting others see you at your worst and most unguarded—while distinguishing between people who hold that against you and those who protect and nurture that vulnerability.
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In love and partnership, when you know, you know—then act like it.
When his now-wife LeAnn broke up with him, Bert realized he couldn’t imagine a good life without her, chose not to numb himself with alcohol, and instead did the emotional work to win her back and commit fully to the relationship.
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Notable Quotes
“The first time I tell it, the first time I tell it, it’s perfect. And then I take it and I try to fix it and make it better and jazzier, and I just fuck it up.”
— Bert Kreischer
“The number one thing my one takeaway from that man is humility. And I applied it in different ways throughout my career.”
— Bert Kreischer on his father
“If you find that thing you love to do, you will work endlessly, effortlessly, and hard as fucking shit every day—and you’ll love every day of your life.”
— Bert Kreischer
“Joe Rogan is the most selfless individual I’ve ever met. He didn’t just take me to the water one time and give me a drink; he gave me a machete and said, ‘This is how I get to the water.’”
— Bert Kreischer
“When you get drunk, like real drunk around someone, you’re giving them a gift. You’re saying, ‘I want you to see me for everything I am.’”
— Bert Kreischer
Questions Answered in This Episode
How does Bert’s belief that ‘the first telling is perfect’ compare to more traditional, iterative approaches to writing and standup?
Bert Kreischer and Lex Fridman dive into Bert’s philosophy of joy, his creative process in standup, and the role alcohol and partying play in his life and persona. ...
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Where is the line between joyful excess and self-destruction in Bert’s relationship with alcohol, and does he see that line shifting as he ages?
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What can other comedians or creators practically learn from Bert’s promotional experiments—like the surgery promo or marching band bit—without copying his exact style?
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How sustainable is Bert’s ‘work endlessly at what you love’ philosophy, and what would it actually look like for him to take a real break?
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In what ways do Bert’s stories about Rogan, Segura, and Whitney reveal a playbook for building loyal, long-term creative friendships?
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Transcript Preview
You know who drank-
What?
... was Churchill.
That's my homie and that's my guy.
Yeah.
You know that's my guy, right?
So he, uh, he did champagne.
No, let me-
Yeah.
You don't have to tell me-
All right.
... a thing about Winston Churchill.
All right. (laughs)
He, I found out about his daily routine.
Yeah.
So his daily routine was a big breakfast, cigar, coffee, eggs sunny side up, toast, bacon, sausage, tomato, beans-
Yeah.
... uh, fruit, orange juice, soft scotch, cigar in bed. And he'd sit there for three hours. And then he'd get in the bathtub and drink champagne. And then he'd go to lunch and have some goose-
Mm-hmm.
... with more champagne. And then he'd take a nap and, like, I love that. So every year on hi- the day of his death, I think it's January 24th, I celebrate Winston Churchill's life by living the way he did.
Mm-hmm.
And so I have breakfast in bed with a soft scotch and I just party all day. That would be the guy to drink with.
The following is a conversation with Bert Kreischer, a standup comedian, podcaster, actor, and a man they call The Machine. I've been a fan of his comedy and podcast for many years, and I highly recommend you watch him on Bertcast, Two Bears, One Cave with Tom Segura, his cooking show called Something is Burning, and, finally, the new movie that tells the story of the man, the legend, The Machine. This is the Lex Fridman Podcast. To support it, please check out our sponsors in the description. And now, dear friends, here's Bert Kreischer. I read somewhere that you like Ernest Hemingway.
Love him.
Now there's a quote, "There's nothing to writing. All you do is sit down at a typewriter and bleed." Do you agree with that?
I agree. I agree. Well, I agree with that with journaling 'cause I, I can't write, um, I can't write standup, like, I can't write a bit, but if I journal I'll find something that I go just right. The kind of writing where your, the pen's moving faster than your brain and they're kinda, like, doing it together. The thing I liked about Earnest Hemingway, this is so stupid, I'm a little dyslexic and so I'm not a good reader. And so he wrote very simply, and it wasn't until after I read a bunch of Earnest Hemingway (laughs) when I was working at Barnes & Noble-
(laughs)
... and this person said, "Don't you love his titles?" And I was like, "Yeah, Sun Also Rises." And they're like, "Yeah, but no, The Sun Also Rises." And I was like, "Yeah. Sun Also Rises." And they're like, "No, The, no, The Sun Also Rises." And I went-
Yeah.
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