Crazy Ex-Girlfriends w/ Big Jay Oakerson | 2 Bears, 1 Cave Ep. 181

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Welcome to another episode of 2 Bears 1 Cave with Tom Segura and guest bear Big Jay Oakerson! Go check out his new comedy special “Dog Belly” on YouTube right now! Tom and Jay talk about the chaotic Ari Shaffir, the shameless Bert Kreischer, and the confident Kevin Hart. They trade stories about TSA encounters, Jay shares stories about coming up with Kevin Hart, getting broken up with and getting caught cheating. They talk about standup comedy, writing, New Faces in Montreal, and the worst intros comedians have brought them on stage with.

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YouTube Chapters
00:00:00 - Intro
00:01:59 - Ari Shaffir is a Menace and Bert is Shameless
00:10:59 - Talking Back to TSA Agents
00:21:24 - Kevin Hart
00:30:04 - Embarrassing Breakups
00:41:07 - Sex, Dating and Cheating
00:56:39 - Owning Your Flaws
01:02:36 - Writing New Jokes
01:09:17 - New Faces in Montreal
01:13:34 - Terrible On Stage Intros, Bobby Slayton and Patrice O’Neal