Joe DeRosa 5K in 11 minutes
Joe DeRosa claimed he ran the 5K in 11 minutes, which Tom Segura described as a new record.
Snapshot · 2 Bears, 1 Cave with Tom Segura & Bert Kreischer
Live from the Rose Bowl | 2 Bears 5K ft. Jelly Roll, Ari Shaffir, Joe DeRosa & Are You Garbage?
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May 18, 2026
Where this was said
Ari Shaffir
At 1:01:42 · chapter starts 49:51
Ari Shaffir arrives having just taught a yoga class at the 5K, heat-stroked and bearded, and the dynamic immediately shifts into the philosophical and anarchic. The group swaps Shaq stories — Ari relays Brett Ernst's anecdote about Shaq spending 90 minutes playing with birthday party children and paying their tab — before pivoting to Joe Rogan's stratospheric fame and the odd experience of realizing your friends have become cultural institutions. [1] — Ari Shaffir "Ari Shaffir relays comedian Brett Ernst's story about Shaq at a restaurant: asked to say hi to children at a birthday party mid-meal, Shaq …" 50:20 Bert unpacks his therapist's framing of his narcissism: he doesn't cheat because he'd be miserable without his wife, not because he cares about her feelings, and the 5K itself is a product of that self-centered drive. The gang then reconstructs 'Fat Tom' with forensic glee — the pecan pie spiral, the hot sauce kit, the body that had 'given up' — before Ari casually drops that he regularly passes blood and has no intention of addressing it. [2] — Bert Kreischer "Bert Kreischer argues that narcissism isn't inherently bad — he only does things because of how they make him feel, including not cheating …" 55:35
Shaq's Generosity: 90 Minutes With Kids, Paid the Tab
Ari Shaffir relays comedian Brett Ernst's story about Shaq at a restaurant: asked to say hi to children at a birthday party mid-meal, Shaq finished eating first, then spent 90 minutes playing with the kids and paid their entire tab before leaving.
Bert's Narcissism Therapy Session
Bert Kreischer argues that narcissism isn't inherently bad — he only does things because of how they make him feel, including not cheating on his wife (he'd be miserable without her) and not talking shit about Tom (Tom hasn't done anything worth it). His therapist agrees.
Tom Segura Bombs in Front of Eddie Murphy... Wait, Wrong Story
Bert and Ari reconstruct 'Fat Tom' — a version of Tom Segura who was broke, binge-made pecan pies, and gained 30 pounds in a month before he knew he had money. Today's Tom has a chef and red light therapy injections. The contrast is wild.
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