Overview of Live from the Rose Bowl | 2 Bears 5K ft. Jelly Roll, Ari Shaffir, Joe DeRosa & Are You Garbage?
This live YMH episode is centered on the 2 Bears 5K at the Rose Bowl and turns into a loose, emotional, very funny celebration of weight loss, recovery, friendship, and fan stories. Bert Kreischer and Tom Segura open with huge crowd energy, then bring up guests including Jelly Roll, H. Foley and Kevin Ryan from Are You Garbage?, Ari Shaffir, and Joe DeRosa. The episode mixes life-affirming stories from the run with crude comedy, celebrity run-ins, and plenty of riffs about being fat, getting healthy, and surviving adulthood.
Main Themes
The 2 Bears 5K as a transformation story
- The race is presented as more than a comedy event—it’s become a community milestone for people trying to get healthier.
- The hosts repeatedly highlight audience members and runners who have:
- lost hundreds of pounds,
- come back year after year,
- met spouses or made major life changes through the event.
- Jelly Roll’s transformation is a major emotional anchor:
- he talks about being nearly 500+ pounds at one point,
- now being down almost 300 pounds,
- and how the race and the “no judgment” environment helped save his life.
Humor about life before and after weight loss
A huge chunk of the conversation is built around jokes about what being very overweight used to be like, including:
- avoiding stairs,
- fear of airplane bathrooms,
- tying shoes awkwardly,
- buying jeans,
- fitting in booths,
- seeing one’s own body again after weight loss,
- and the sheer absurdity of “fat guy logistics.”
The jokes are filthy, but the underlying point is serious: weight loss changed mobility, confidence, and quality of life.
Friendships and “fully honest” banter
The conversation between the comics feels very lived-in and personal:
- Tom and Bert joke about each other’s old weight, habits, and health.
- “Fully honest” becomes a recurring bit, especially with Joe DeRosa, who is described as never exactly lying but also never quite telling the truth.
- There’s constant teasing about:
- phone numbers disappearing,
- text-message chaos,
- drunken behavior,
- and who can or can’t be trusted.
Notable Guest Moments
Jelly Roll
- Jelly Roll is treated like the emotional third bear of the event.
- He describes his weight-loss journey and emphasizes how the event gave him hope.
- The hosts and audience celebrate his progress as a life-saving change.
Are You Garbage? (H. Foley & Kevin Ryan)
- Their segment leans into:
- Florida stereotypes,
- trashy behavior,
- “garbage” life choices,
- and food/drink jokes.
- They joke about a fantasy “Two Gram K” instead of a 5K, with beer, hot dogs, tomato pie, water ice, and escorts.
- Kevin and Foley fit right into the chaos and get into the running/weight-loss banter.
Ari Shaffir
- Ari jokes about:
- teaching yoga before the race,
- being heat-stroked,
- and not running the event.
- He and the others riff on celebrity culture, Shaq, Joe Rogan, and being in “the files” in a joking Epstein-related exchange.
- Ari also plugs his travel podcast You Be Trippin’ and presents Bert with the Trippie Award for best trip/episode.
Joe DeRosa
- Joe arrives late, jokes that he ran the 5K clean, and becomes a key part of the final stretch.
- He talks openly about:
- drinking,
- testosterone shots,
- weight loss,
- a belly button/hernia issue,
- and shitting blood in a way that only Ari could top with worse details.
- His chemistry with the group is especially strong—he’s one of the most natural “insult comedy” fits in the room.
Repeated Jokes and Running Bits
- Bert’s penis: repeated jokes about dick casts/statues, showing it off, and how long everyone has seen it.
- Old fat life vs. new healthy life: the crew keeps returning to how much easier everything is now.
- Celebrity encounters: Shaq, Eddie Murphy, Kevin Hart, Joe Rogan, and others are used as stories to flex friendship and absurdity.
- Phone problems and identity drift: DeRosa’s lost phone and forgotten Apple ID become a metaphor for modern dysfunction.
- Epstein jokes: the conversation repeatedly veers into dark, absurd territory with joking references to “the files,” proving the show’s commitment to unfiltered shock humor.
Announcements and Plugged Projects
Media and projects mentioned
- Tom Segura plugs Very Bad Thoughts / Bad Thoughts on Netflix.
- Bert Kreischer mentions Free Bert streaming on Netflix and promotes the event/community.
- Ari Shaffir plugs You Be Trippin’.
- The hosts also mention the broader YMH ecosystem and upcoming content.
Sponsors briefly featured in the live recording
The episode includes ad reads for:
- Saley eSIM
- Manscaped
- BetterHelp
- Hims
- ShipStation
- MARS Men These are standard podcast sponsor spots woven into the live show.
Key Takeaways
- The 2 Bears 5K has evolved into a surprisingly meaningful community event for people changing their lives.
- Jelly Roll’s weight-loss story and the audience members’ transformations give the episode a genuinely uplifting backbone.
- The comedy stays dirty and chaotic, but the core message is clear: the event makes people feel seen, welcomed, and capable.
- The live show works because it balances:
- emotional gratitude,
- insult-comedy chemistry,
- and unfiltered absurdity.
Final Impression
This is a classic YMH live episode: loud, filthy, and deeply funny, but also unexpectedly heartfelt. Under the nonstop riffing, the event comes across as a real celebration of health, resilience, and community—with Bert and Tom using comedy to make a fitness milestone feel like a victory lap for everyone involved.