Bert Kreischer appeared on Jimmy Kimmel Live on August 27, 2026, with Jelly Roll guest hosting. On paper that is two friends turning a long friendship into a network television segment. What aired was the story of how that friendship rearranged both of their lives, told by the two people it happened to.
What Is the 5K by May Challenge?
The 5K by May challenge was an open dare from Bert Kreischer and Tom Segura on their podcast 2 Bears, 1 Cave: get yourself to a 5K by May. It was the kind of thing said on a podcast every week and forgotten by Thursday.
Jelly Roll was listening, and Jelly Roll took it. He accepted the challenge in January 2024 and has never been shy about where he started from. "I couldn't walk a mile when I started trying to do this back in January," Jelly Roll told Fox 4's Ashley Hume at the finish line that May.
How Did the 2 Bears 5K Start?
The 2 Bears 5K grew directly out of that challenge. The first one was run in May 2024 at the Rose Bowl in Pasadena, California, as part of the Netflix Is a Joke Festival, with more than 1,400 people taking part in person and virtually. It has been run every May since, and it has never had timers or a competitive bracket. It has a dab station on the course.
Jelly Roll finished that first race, and so did Bert Kreischer. The part Bert kept returning to at the Kimmel desk was the finish line itself: both of them crossed it, both of them were crying, and both of their wives were standing right there.
"He Will Jump Off a Cliff With You"
That is Jelly Roll's summary of what Bert Kreischer is like as a friend, and he did not mean it as a compliment about restraint. He meant that Bert shows up. If you are having the worst night of your life, Bert is having it with you.
Bert Kreischer framed the same thing from the other side. The friendship has been built on saying wild things out loud and then following through on them. It sounds like a bit. It turns out to be an operating principle, and it is the reason a throwaway line on a podcast ended up as an annual race with a Netflix festival attached.
What Else Bert Talked About on Kimmel
Bert Kreischer also spoke candidly in the segment about a hard stretch he had been through, including the panic attacks that came with it. He told it the way he tells everything, which is to say he got a room full of strangers laughing at the worst night of his life. That part is worth hearing from him rather than reading about, and the full segment is above.
He also used the appearance to talk up Fully Loaded at Sea, the comedy cruise he hosts, which is the same instinct in a different form. Current dates, lineups and tour routing live on the tour page and at bertkreischercruise.com.
The Point
Bert Kreischer says wild things out loud. Sometimes it is a 5K in May. Sometimes it is a boat. The consistent part is that he follows through, and that a guy listening at home heard him do it once and decided it applied to him too. That is the whole story of that Kimmel booking, and it is why both of them were on that stage to begin with.
About this article: Original commentary from Berty Boy Productions, with links to reporting by Ashley Hume at Fox 4 and Rachel Stone at BroadwayWorld. Segment courtesy of Jimmy Kimmel Live. Last reviewed October 2026.
