Club Shay Shay – Bert Kreischer Part 1

Podcast: Club Shay Shay
Host: Shannon Sharpe
Guest: Bert Kreischer
Date: January 21, 2026

Episode Overview

In this lively episode, NFL Hall of Famer Shannon Sharpe welcomes comedian, storyteller, and "party legend" Bert Kreischer. Their wide-ranging conversation traverses Bert's career trajectory, comedic inspirations, challenges with self-identity, reflections on sudden fame, personal relationships, infamous partying years at Florida State, and encounters with showbiz heavyweights. The tone is candid, heartfelt, and often hilarious, with memorable anecdotes and self-deprecating humor.

Key Discussion Points & Insights

1. Bert’s Public Persona and New Netflix Show

• Identity on Stage and Off (04:27–06:00 & 06:16–08:02)
  • Bert discusses how his comedic persona often blurs with his real self.
  • He always plays a variation of "Bert" in his projects and draws heavily from his life experiences.
  • Bert opens up about struggles with an ongoing identity crisis, shaped by early struggles and later success.
  • He reflects on the juxtaposition between his wild, shirtless stage reputation and his life as a dad/husband.

“I've always had an identity crisis because I do have this moniker in 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 am a husband.” (Bert Kreischer, 04:42)

• Success, Guilt, and Changing Relationships (08:02–10:13)
  • Bert talks about feeling guilty over his newfound wealth, how friends and other comics treat him differently.
  • His podcast dynamic changed as he became more successful, with fellow comedians wanting career advice instead of just banter.
  • He and Shannon bond over the tension between success and loyalty to their roots.

“I never changed. But people see you as change. They see you as like, 'Oh, I remember going to the club and there was this comedian was like, Oh, I didn't know you still did comedy clubs. I thought you just did stadiums.'” (Bert Kreischer, 09:00)

2. The Legendary ‘Rolling Stone’ Article and Its Impact

• Becoming “The Machine” (12:07–14:18)
  • Bert’s legendary party reputation at Florida State was immortalized in a Rolling Stone article.
  • Describes how the reporter found him (by partying with various student groups), and how the story shifted focus entirely to Bert.
  • The article led to major life changes: encouragement from family/friend figures to chase stand-up dreams in New York.

“I was an open book. My policy with everything with podcasting, with Stand up has always been over, tell the truth, overshare. And when People go, that's too much information, I go, not until you start gagging.” (Bert Kreischer, 13:10)

3. Florida State, Self-Promotion, and Storytelling

• Stories vs. Humility (19:49–21:18)
  • Bert admits he wasn’t a self-promoter in college—he preferred others telling his stories. Stand-up forced him to embrace self-promotion and storytelling.
  • Shifted to crafting routines from real-life mayhem (e.g., acid in Disneyland) and blending events for comedic effect.

“Before I got into this business, I wasn't a self promoter… But when I got into stand up, I realized, if you're not promoting yourself, no one's promoting you.” (Bert Kreischer, 20:07)

• The Family as Comedy Gold (24:43–31:40)
  • Bert credits humorous family anecdotes, especially involving his daughter Isla, for much of his stand-up success and even offers her money for rights to her lines.
  • Story: negotiating with Isla over a killer joke—"buddy, when you die, I get all the money." (25:08–25:38)
  • His daughters are closely exposed to comedy's inner world but have no interest in following his or his peers’ footsteps.

“[Isla] goes, buddy, when you die, I get all the money. That kid goes through my Rolexes and earmarks the ones she wants.” (Bert Kreischer, 25:38)

4. Early Life, Sports, and Finding Comedy

• From Athlete to Comedian (34:54–42:56)
  • Bert was a serious baseball player, recruited by Duke and The Citadel, but left sports for fraternity life and discovered his knack for making people laugh.
  • Realized—after a pivotal conversation with his dad—that comedy, not athletics, was his personal “thing.”

“Your goal in life is to find your thing the way Brad found baseball.” (Bert Kreischer, 40:18)

• Early Stand-Up Moments (41:42–42:56)
  • Early experiences included doing stand-up on bus trips and realizing his wit was his true strength.

5. Personal Stories: Relationships, Vulnerabilities, & Betrayals

• Romantic Misadventures (42:59–46:27)

  • Bert shares a painfully awkward story of losing his virginity and how that shaped his cautious approach to relationships.
  • He values long-term connections over one-night stands, has only been with six women, and considered himself “not built” for casual flings.

• College Betrayals (47:31–51:05)

  • Talks about being cheated on by a long-term girlfriend—with his roommate. The betrayal left a lasting mark, but eventually forgiveness.
  • Bert discusses the deep hurt of being blindsided by infidelity, discovering all his friends had known.

“It is an embarrassing feeling to be cheated on. And everyone know about it but you.” (Bert Kreischer, 49:16)

6. Hollywood, Van Wilder, and Career Turning Points

• Van Wilder Origin (53:06–55:14)
  • Confirms that “Van Wilder” was based on his Rolling Stone story, though he wasn’t officially involved with the film and chose not to sue to preserve future industry opportunities.

“Barry Katz was on that phone, my old manager... 'Papa, there’s two types of people in this business. People who work and people who sue. Pick which one you want to be.' And I went, I want to work. And he goes, then don’t sue.” (Bert Kreischer, 54:15)

• Move to New York and the Reality Check (59:58–64:49)
  • After being pushed by his dad, Bert moves to New York and realizes the grind is much harder than anticipated. His father’s tough love conversation spurred him to start “barking” (audience recruiting) at clubs for stage time.

“You wanted help. This is how it works. Do it again. It's persistence.” (Bert Kreischer’s Dad, 64:53)

7. Showbiz Mentorship: Meeting Will Smith

• Will Smith Encounter (68:30–77:06)
  • A serendipitous meeting with Will Smith leads to Bert's first six-figure TV development deal.
  • Shares hilarious confusion and anxiety over a series of meetings with Will Smith and hip-hop legends, including being taught about TV pitches and business.
  • Will’s lasting advice, given at a urinal: “Just be yourself.”

“And the last thing you need to know is just be yourself. And I went, that's the only thing I heard.” (Will Smith to Bert Kreischer, 76:48)

Notable Quotes & Memorable Moments

• “I literally... I'm very introspective. I'm in therapy, and I'm trying to figure things out.” – Bert Kreischer, 06:16
• “Sometimes you have success and then you go back to the club, and you're like, God, man, it was weird. Cause I never changed. I never changed. But people see you as change.” – Bert Kreischer, 09:00
• “That kid goes through my Rolexes and earmarks, the ones she wants. There's little I's written on the back of them.” – Bert Kreischer, 25:38
• “You want to work or you want to sue?” – Barry Katz, via Bert Kreischer, 54:15
• “My goal in life is to find my thing the way Brad found baseball.” – Bert Kreischer quoting his father, 40:18
• “I want to work. And he goes, then don't sue. And I didn't sue. And I've worked my entire life.” – Bert Kreischer, 54:22
• “He told me, be myself... at a urinal. And the last thing you need to know is just be yourself.” – Bert Kreischer, 76:48
• “It's devastating to be cheated on and to have a community know about it and you not know about it? ... It really... it's defining. It's traumatic.” – Bert Kreischer, 50:09

Important Timestamps

• Identity & Stand-Up Persona: 04:27–10:13
• Rolling Stone's Influence: 12:07–14:18
• Storytelling Evolution: 19:49–23:33
• Family as Material: 24:43–31:40
• High School & College Transition: 34:54–41:42
• Loss of Virginity confession: 43:03–46:27
• Cheated by Roommate: 47:31–51:05
• Van Wilder Legal Drama: 53:06–55:14
• Dad’s NYC Intervention: 62:15–64:53
• Meeting Will Smith: 68:34–77:06

Tone & Style

Candid, irreverent, self-deprecating, and rich with personal anecdotes. The conversational style is both vulnerable and hilarious, with Bert openly discussing shortcomings, private pain, and moments of triumph. The interplay between Shannon’s straightforward warmth and Bert’s honesty creates an engaging, easygoing experience for listeners.

For Listeners New to the Episode

This episode is packed with wild college tales, surprising showbiz encounters, and deep personal reflection. Above all, it captures Bert Kreischer’s philosophy—using authenticity, honesty, and perseverance to forge a remarkable comedic career.

For the continuation of Bert’s story, check out Part 2 of this Club Shay Shay conversation.