2 Bears, 1 Cave with Tom Segura & Bert Kreischer

Podbit · 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?

Explore episode May 18, 2026

Where this was said

Jelly Roll aka The Third Bear

At 13:55 · chapter starts 2:50

Jelly Roll arrives to a hero's welcome and immediately the conversation goes deep. Bert introduces him as having crossed the finish line of the first 5K at over 500 pounds and now weighing in somewhere between 250 and 270. The stories that follow are both hilarious and devastating: counting stairs before entering a venue, Googling restaurants to zoom in on chair width, being unable to turn around in airplane bathrooms and having to back in to use the toilet, tying shoelaces off to the side because bending down is out of the question. Jelly Roll reveals the emotional core — he was drinking a liter of tequila a day, weighed 500 pounds, and knew he had no more than 30 more months left in him. The 2 Bears 5K was the non-judgmental, come-as-you-are space he needed. He tallies up the weight lost by just five people he knows at the event and arrives at 1,000 pounds. The segment closes on a lighter note: Bert sent plaster casts of his penis to friends to celebrate Free Bird, and Jelly Roll's is displayed on his mantle next to a Bible.

Similar podbits

Comedy
Bobby Walked 7 Miles Home With Dicks on His Face

Tortilla Face · Aug 10, 2026 Comedy

At a childhood sleepover in Sacramento, Bobby Lee's friends drew penises all over his face while he slept. He woke up, cried, and walked 7 miles down a dirt road before Eric Purvis's mom drove out to retrieve him.

Comedy
Cracking the Aladdin 9/11 Code

Tortilla Face · Aug 10, 2026 Comedy

Their producer riffs a conspiracy theory about Lindsey Graham's death in Kyiv, which somehow leads to Bobby and Andrew discovering that every lyric of 'A Whole New World' from Aladdin secretly describes 9/11. They are disturbingly convincing.

Comedy
The Caddyshack Drug Revelation and Their Dream Movie

Tortilla Face · Aug 10, 2026 Comedy

Harold Ramis told a story about Caddyshack's cast doing drugs all day and night during Florida storm delays, with half their pay going to cocaine. Bobby Lee immediately wants to make that exact movie — and offers to relapse to do it.

Comedy
The Towel Story: Rich People Have New Towels

"Robby Hoffman" · Aug 10, 2026 Comedy

Robby Hoffman had never heard of 'new towels.' A towel, in her world, was built with the house. When Sarah Silverman announced she'd bought new pool towels, it was a class-gap revelation.