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Ari Shaffir sits in for Tom Segura with Bert Kresicher for this episode of 2 Bears, 1 Cave. Ari and Bert discuss the "NYC Still Rising After 20 Years" comedy benefit at Madison Square Garden that Tom performed at. They try to guess the lineup which also included Jimmy Fallon, Jon Stewart, Pete Davidson, Amy Schumer, Dave Chappelle, Chris Rock, Bill Burr, John Mulaney and many more. Bert shares a video from a surfer who talks about exploiting places you visit, which leads to a conversation about geo-tagging. They also talk Bert's Red Rocks show, Sober October, ugly people wearing face masks, and debate about which of them is the better backgammon player.

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