The episode opens with Tom Segura delivering a pre-baked ad for Ciccio Bomba, his Italian bakery now at three Austin locations, inviting listeners to come rub the belly on his statue. When the live show proper begins, Bert and Tom hit the stage dripping — Tom's calf cramped on the walk up, Bert's toenail is threatening to exit his foot. They welcome the crowd to the third annual 2 Bears 5K at the Rose Bowl, note personal bests being set, and toss good-natured barbs at the fans in their novelty t-shirts before setting up what promises to be a revolving door of comedian guests.

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 Play} 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 Play} 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.

After Jelly Roll's emotional segment, H. Foley and Kevin Ryan bring the energy back to gleeful chaos. Foley is down 50 pounds and Kevin is down 75, but the real story is Foley's digital collapse: his phone got wet, he forgot his Apple ID, and Apple shut down his Uber, Venmo, Seamless, and every other app simultaneously. Kevin reads the panicked, unpunctuated email Foley sent from a laptop — which includes his Hell's Kitchen address and closes with 'I love you both. Hopefully to talk to you soon, Henry' — to hysterical reaction. ^{[1] — H. Foley "H. Foley's phone got wet, he forgot his Apple ID, and Apple nuked his entire digital life. Kevin Ryan reads aloud the single run-on email F…" 39:27 Play [2] — H. Foley "H. Foley down 50 lbs: H. Foley from Are You Garbage? shared he is down approximately 50 pounds." 26:05 Play} Between bits, Bert defends himself against Tom's revelation that he appears in the Epstein files ('I was in his email because he was a big fan of comedy'), the gang discovers Bert's Gmail is [email protected] after it was accidentally sent to the Girl Scouts, and Bert delivers a vivid account of his first bidet experience in Japan that escalated quickly.

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 Play} 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 Play}

Joe DeRosa closes the guest rotation, strolling on looking suspiciously fresh for someone who was drinking every night in Austin and naturally wakes up at 9 AM due to anxiety — and occasionally wets the bed. He claims a blistering 11-minute 5K time to Tom's mock astonishment. ^{[1] — Ari Shaffir "Ari Shaffir returns from a world travel sabbatical and surprises Bert Kreischer with a 'Trippy Award' for best episode of his travel podcas…" 1:00:15 Play} The emotional highlight of the closing stretch belongs to Ari Shaffir, who surprises Bert with a legitimate Trippy Award — no turd in the box — for best episode of You Be Trippin', awarded for Bert's Vietnam trip. Bert receives it with genuine delight. The crew cycles through plugs: Ari's This Is the End on YMH with a live $5 discount code, Joe's new podcast Vile and Horrendous, Tom's Bad Thoughts on Netflix (May 25th), and another push for Ciccio Bomba. Bert closes with an improvised rhyming outro over the theme, promising the 5K returns next year in a new city.

Joe DeRosa closes the guest rotation, strolling on looking suspiciously fresh for someone who was drinking every night in Austin and naturally wakes up at 9 AM due to anxiety — and occasionally wets the bed. He claims a blistering 11-minute 5K time to Tom's mock astonishment. ^{[1] — Ari Shaffir "Ari Shaffir returns from a world travel sabbatical and surprises Bert Kreischer with a 'Trippy Award' for best episode of his travel podcas…" 1:00:15 Play} The emotional highlight of the closing stretch belongs to Ari Shaffir, who surprises Bert with a legitimate Trippy Award — no turd in the box — for best episode of You Be Trippin', awarded for Bert's Vietnam trip. Bert receives it with genuine delight. The crew cycles through plugs: Ari's This Is the End on YMH with a live $5 discount code, Joe's new podcast Vile and Horrendous, Tom's Bad Thoughts on Netflix (May 25th), and another push for Ciccio Bomba. Bert closes with an improvised rhyming outro over the theme, promising the 5K returns next year in a new city.