1,000 lbs lost in the crowd
Jelly Roll tallied the weight lost by just the five stories he personally knew at the 2 Bears 5K event, totaling 1,000 pounds across five people.
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 11:20 · 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. [1] — Jelly Roll "Jelly Roll reveals he was drinking a liter of tequila a day at 500 pounds and didn't have 30 more months left to live. The 2 Bears 5K was t…" 09:13 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. [2] — Jelly Roll "That is 1,000 pounds in just us that have been lost. Just these are the 5 stories I know." 11:35 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.
Jelly Roll down ~300 lbs
Jelly Roll started the 2 Bears 5K journey at over 500 pounds and now weighs between 250 and 270 pounds, a loss of nearly 300 pounds.
The 2 Bears 5K Community Effect
Jelly Roll describes a fan who heard about the first 5K, lost 300 pounds to run the second, met his wife at the Tampa race, and is now back for a third year with her. It's the purest distillation of what the event has become.
Fat Guy Problems: Airplane Bathrooms, Shoelaces & Roller Coasters
Jelly Roll and Bert Kreischer trade stories about the embarrassing logistics of being extremely obese — counting stairs at venues, backing into airplane bathrooms to avoid needing to turn around, tying shoes off to the side, and never fitting on a roller coaster until age 41.
Jelly Roll's first roller coaster at 41
Jelly Roll rode a roller coaster for the first time ever at age 41 after losing weight, having previously been too large to ride.
Jelly Roll Discovers His Own Dick
Jelly Roll hadn't seen his own penis in 30 years due to his weight. The Hey Macarena was the biggest song on the radio the last time he had. Now that it's back, he says it looks like a pug — nose finally out but draped to the side.
Jelly Roll: The 5K That Saved My Life
Jelly Roll reveals he was drinking a liter of tequila a day at 500 pounds and didn't have 30 more months left to live. The 2 Bears 5K was the jolt he needed — and now he's nearly 300 pounds lighter and shaved 14 minutes off his race time.
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