2 Bears, 1 Cave with Tom Segura & Bert Kreischer

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?

Explore episode May 18, 2026

Where this was said

Jelly Roll aka The Third Bear

At 13:11 · 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.

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