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Tom Segura and Bert Kreischer are back together again for episode 100 of 2 Bears, 1 Cave! They talk about the "NYC Still Rising After 20 Years" comedy benefit that Tom performed at with Bill Burr, Amy Schumer, Jon Stewart, Dave Chappelle, Pete Davidson, and many more. Tom reveals that he got very drunk and embarrassed himself in front of Serena Williams and Alexis Ohanian, and shares the interaction he had with one of his comedy idols, Chris Rock. They discuss doing Sober October again, another live show, and Bert reveals the nightmare he had getting through the Denver airport with his family.

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