2 Bears, 1 Cave with Tom Segura & Bert Kreischer New Year New Roast | 2 Bears, 1 Cave
Jan 5, 2026
Join the hosts as they hilariously dissect the awkwardness of first-class travel and share their most chaotic air travel stories. They reminisce about childhood influences from SNL and recount the pressure of roasting the Jersey Shore cast, debating whether to pull out of the gig. Expect some wild brainstorming of roast jokes, reflections on New Year's resolutions, and the realities of performing on holiday nights. There’s plenty of laughter and a touch of regret as they close the Winter Bears chapter!
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First Class Changes Behavior
- Stavros and Chris joked about first-class constraints stopping "latent homosexual" antics.
- They reminisced about old flights where privacy in the back allowed sneaky behavior.
Prioritize Family-Friendly Tour Choices
- If a gig conflicts with family priorities, choose proximity over prestige.
- Chris plans to base shows in the original 13 colonies to stay near family.
Canceled Tours To Prioritize Home
- Chris canceled the last quarter of his shows to stay home with family.
- He felt distance and multiple time zones harmed his mental state.