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Bert Kreischer is out for this episode of 2 Bears, 1 Cave, but Roy Wood Jr. joins Tom Segura in his place. Roy and Tom talk about Roy’s podcast "Roy’s Job Fair" in which he interviews people with interesting jobs. This leads Roy to discuss the various jobs he had when he was young, including one where he worked in a hospital kitchen with a man who was stealing pills from the patients. Roy also discusses getting arrested, and working at Golden Corral while he was on probation. Tom and Roy also talk about cancel culture, Shane Gillis being fired from SNL, Janet Jackson’s Super Bowl nip slip, and the times Roy got suspended on terrestrial radio. Roy recounts his experience taking over for Ari Shaffir as the host of "This Is Not Happening," and the backlash Ari got for his Kobe Bryant tweet. Tom and Roy wrap up by discussing airplane etiquette, and the time Roy accidentally played an "adult video" on a plane.