Club Shay Shay – Bert Kreischer (Part 2)
Podcast: Club Shay Shay
Host: Shannon Sharpe
Guest: Bert Kreischer
Release Date: January 21, 2026
Episode Overview
In Part 2 of his appearance on Club Shay Shay, comedian Bert Kreischer joins Shannon Sharpe for a fast-moving, story-filled conversation. They dive into Bert’s most infamous stories (the Russian Mafia tale), his perspective on storytelling and comedy, the highs and lows of his financial journey, viral moments in stand-up history, and inside looks at the Netflix Tom Brady roast. The episode is full of candid advice for up-and-coming comedians, commentary on luck versus hard work, reflections on fame and relevance, and Bert’s signature blend of boisterous humor and authenticity.
Key Discussion Points & Insights
The Russian Mafia Story: Origins and Legacy
[01:33–12:22]
- Shannon brings up Bert’s legendary “Russian mafia” college story – a tale Bert is widely credited with turning into viral comedy gold.
- Bert discusses the origins:
- First told the story on Loveline with Dr. Drew; it became his brand-defining bit.
"Dr. Drew said to me, 'This is your story. This is your movie.'" (08:00)
- Initially skeptical about telling such a long story on stage (“Standup comedy should be done in small bites”), Bert was encouraged by Joe Rogan to make it a cornerstone of his set.
- First told the story on Loveline with Dr. Drew; it became his brand-defining bit.
- The impact:
- Verified online by classmates; the story went viral, driving a huge wave of new fans and ticket sales.
- Bert reflects on that legendary moment:
"It was like 3 million views, 5 million, then 7 million... 30 million, 40 million, 50 million. And then all of a sudden, every show's sold out." (10:46)
Storytelling in Comedy & Truth Versus Entertainment
[04:22–07:19]
- Bert explains that as a storyteller, his mandate is to entertain—factual accuracy comes second.
"I'm a storyteller. It's based in truth, but it's gotta be funny." (04:41)
- He shares his experience with the Tracy Morgan story controversy and the eventual blessing from Morgan to keep telling it, underlining the unpredictable line between fact, memory, and performance.
The Importance of Luck in a Comedy Career
[20:41–24:28]
- Bert argues that luck is pivotal—sometimes even more than hard work—for a standout comedy career.
“I believe in luck more than I do hard work.” (20:41, 24:19)
- Illustrates with famous stories of career luck/virality—Bill Burr’s Philadelphia rant, Jim Jefferies’s onstage assault, and Joe Rogan’s public confrontation with Carlos Mencia.
“Every comic has that one lucky moment, that one crazy moment that happens to them, and that makes you relatable.” (23:12)
Rebuilding After Financial Struggles
[24:28–27:27]
- Bert shares his own reckless spending in his 20s and facing sudden tax debt while starting a family.
“You're spending money like you have cancer.” (24:54)
- His wife’s feelings of “bad luck,” and Bert’s enduring belief that money will show up again.
“I have so much good luck that my good luck will overwhelm you, and you're going to be lucky soon. Don't worry. We're going to get through this.” (26:27)
Honesty and Vulnerability in Marriage & Jokes
[27:27–29:44]
- Stories about sharing financial burdens in marriage and the realities of accruing debt together, including a joke his wife hated.
“We should have anal sex ... for 25 f***ing thousand dollars.” (27:54)
- Bert’s comfort in oversharing on podcasts, sometimes forgetting that “people are gonna hear this.”
“Sometimes you do a podcast, you forget people are gonna hear this.” (30:03)
The Tom Brady Netflix Roast: Backstage and Onstage
[31:12–36:28]
- Bert details his participation in the Tom Brady roast and how it evolved from a typical roast slot to a Sportscenter parody with Tom himself.
“I said, I'll do it, but I would love to do it with Tom and I'd love to do something different.” (31:20)
- Recalls Nikki Glaser’s show-stealing set and the backstage realization that her career was about to fundamentally change.
“We were watching someone's life change. ... She’s never going to be the same.” (33:15)
- Stories of Chappelle hanging out in the green room, wild post-show moments, and Gronk’s infatuation with meeting Bert’s wife and Chappelle.
Roasts: Boundaries & Tough Audiences
[38:51–41:52]
- Dissects what goes on and off-limits at celebrity roasts; why Bert feels he’s not a classic roast comic.
- Relays being pushed into tough jokes with Cole Hauser and Kid Rock at other roasts and unanticipated challenges backstage.
Jokes You Won't Tell & Working Around Offense
[42:45–45:24]
- Bert discusses today’s sensitivities and the lines he won’t cross—acknowledging a particularly good joke with an N-word punchline he won’t tell.
“I had a joke where the punchline was the N word. And it's so good. It's so good. I can't tell it.” (43:25)
- Describes how challenging it is to craft edgy material without being offensive, and how it’s a creative challenge he enjoys.
Viral Moments and Internet-Breaking Interviews
[45:24–49:26]
- On Shannon’s viral Katt Williams interview—Bert praises the format and organic chaos.
“That was two guys talking as if you didn't know anyone was listening.” (49:11)
- Parallels between old-school Rogan, when few realized the size of the audience, and the authenticity that creates viral, lasting content.
Comedy Hierarchies & The Unfollowable Ralphie May
[54:21–56:50]
- Bert on who is truly 'unfollowable' in stand-up:
“There’s not one person alive that I would follow... but there’s one person dead who I would to this day and never in my life ever want to follow, and that’s Ralphie May.” (54:21)
- Describes Ralphie May’s legendary ability to dominate a room so fully it couldn't be reset.
Reflections on Success, Money, Fame, and Relevance
[64:24–69:22]
- Discusses the psychological effects and shifting meaning of financial security, spending, and fame with Shannon.
“The money's not real. It's just a number on a computer. ... So then what's the point?” (66:00)
- Revelations about survivor’s remorse, envy from others as you rise, and how to maintain respect for your own journey and for peers' successes.
Embracing Authenticity & Speaking Style
[71:54–73:22]
- Shannon and Bert reflect on career uniqueness—Shannon referencing overcoming expectations about his southern accent and style for TV, while Bert notes his own speech impediment and how it's become part of his charm.
Notable Quotes
-
On Storytelling:
"I'm a storyteller. It's based in truth, but it's gotta be funny."
(Bert Kreischer, 04:41) -
On Going Viral:
"That story went viral like crazy. ... every show's sold out."
(Bert Kreischer, 10:46) -
On Luck vs. Hard Work:
“I believe in luck more than I do hard work.”
(Bert Kreischer, 20:41) -
On Viral Comedy Moments:
"Every comic has that one lucky moment, that one crazy moment that happens to them, and that makes you relatable."
(Bert Kreischer, 23:12) -
On Financial Struggles:
“You're spending money like you have cancer.”
(Bert Kreischer repeating his business manager, 24:54) -
On the Tom Brady Roast/Watching Nikki Glaser Break Out:
"We were watching someone's life change. ... She’s never gonna be the same."
(Bert Kreischer, 33:15) -
On Being 'Unfollowable':
"Ralphie [May] was unfollowable. ... He would take one premise and give you 20 punchlines. ... No one does that."
(Bert Kreischer, 54:53, 56:05) -
On Authenticity in the Media:
“Once I embraced who I was ... you're a legend.”
(Bert Kreischer to Shannon Sharpe, 72:56)
Memorable Moments & Timestamps
-
Tracy Morgan conversation & blessing to retell the story:
[04:53–07:19] -
Bert’s first viral Russian Mafia story appearance on Loveline:
[07:21–08:12] -
Classmate confirms Russian Mafia story online, posts pictures:
[09:26–10:46] -
Reflection on viral nature & instant impact on Bert’s career:
[10:46–11:46] -
Discussion on what makes a story “your story” and the role of storytelling in comedy:
[12:22–13:12] -
Debate on luck vs. hard work—examples from Burr, Jefferies, Rogan:
[21:11–24:19] -
Kevin Hart, luck, and relatability in comedy success:
[20:41–24:19] -
Handling money, debt, and financial missteps:
[24:28–29:44] -
Bert’s joke about his wife’s student debt and her reaction:
[27:54–28:26] -
The Tom Brady roast: backstage, Nikki Glaser, Chappelle in the green room:
[32:16–36:28] -
Boundaries at celebrity roasts, joke writing under pressure:
[38:51–41:52] -
Naming Ralphie May as ‘unfollowable’:
[54:21–56:50] -
Discussion on how Bert and Shannon value authenticity and refusing to shed regional/speech markers:
[71:54–73:22]
Guest Advice and Reflections
For Up-and-Coming Comedians
- Don’t take anyone’s advice blindly:
“The best advice is don't take anyone's advice.” (17:04)
- If you do one thing, “be undeniable”—stand out so much no one can ignore you. (20:17)
- Don’t rush to film a special—wait until you’re genuinely ready, and let your core material develop.
On Handling Fame and Professional Rivalry
- Haters will emerge as you rise—survivor’s guilt is real.
- Don’t harbor ill will; appreciate others’ success and use it as motivation, not fuel for resentment.
"That's a loser's mentality. ... What kind of loser looks at that?" (69:22)
Tone and Atmosphere
Candid, warm, and frequently uproarious—Bert’s fast-paced riffing is perfectly in sync with Shannon’s grounded, direct style. The chat is peppered with self-deprecating humor, unfiltered opinions, stories both wild and relatable, and genuine advice. The conversation oscillates between laughter over outrageous life moments and meaningful honesty about ambition, struggle, and personal growth.
For Listeners
This episode is required listening for standup fans, working comics, or anyone interested in how stories, luck, and authenticity shape a public career. With its deep dives into myth-making, viral moments, and the mental game behind the scenes of show business, Bert and Shannon offer a masterclass in both candor and entertainment. Whether you’re a diehard Machine fan, a comedy nerd, or just love stories about resilience, this Club Shay Shay is not to be missed.