What was supposed to be an inoffensive office prank-putting a whoopee cushion on a dude’s chair before the start of a business meeting-immediately goes off the rails. The Whoopee Cushion Coworker (“Pink Bag”) I HOPE YOU FUCKING DIE, HARLEY JARVIS! 28. It’s an exhaustive ordeal, but like the characters of Robinson’s series, I have backed myself into a corner suggesting this idea to an editor, and the only way out is making content. In that spirit, we’re ranking the best characters from I Think You Should Leave’s first season, with one person (or Chunky) taken from each of the 29 sketches. But whether it’s a chaos agent refusing to back down from an unwinnable situation or the hapless schmoe caught in their way, each sketch has at least one standout character who burrows into your psyche-for better or worse. The show’s sketches live and die by its cast of eccentric characters, played by a combination of Robinson, cocreator Zach Kanin, frequent collaborator Sam Richardson, Saturday Night Live vets, legendary comedians, and even a 2021 Oscar nominee. It’s weird, wonderful, endlessly rewatchable nonsense. The Netflix sketch series, which has left such an impression that even politicians turn to it for memes, typically revolves around awkward social situations where a person refuses to acknowledge the error of their ways until the tension reaches some kind of absurdist breaking point, such as having multiple attendees at a birthday party eat gift receipts to determine whether paper or fecal matter from a Sloppy Mudpie™ was responsible for a stomach ache. (If you love the show and the NBA, boy do we have a niche Twitter account for you.) To watch the first season of I Think You Should Leave With Tim Robinson is to be indoctrinated into a harmless yet exceptionally stupid online cult-one where “You have no good car ideas!” is an epic burn and “The Bones Are Their Money” is the hit song of the summer.
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