I Think You Should Leave Is Indescribable; Here’s A Blog Post About It

So, I wrote this way back when season two premiered, and then I never posted it anywhere. Oops! I found it the other night and was like, “Hey, I should use this,” so… here it is!

There is a sketch in the second episode of the second season of the Tim Robinson-led Netflix sketch show I Think You Should Leave that I haven’t stopped thinking about since I watched it. It’s actually the sketch that opens that episode—a spoof of Shark Tank called The Capital Room.

It starts simply enough, introducing the four investors that contestants will need to wow. The first three have traditional business backstories. “I started in the mailroom and worked my way to the head of the boardroom,” one of them declares. Another talks about how she started with a single sunglasses kiosk in a mall before expanding into an international chain.

“I sued the city after I was accidentally sewn into the pants of the big Charlie Brown at the Thanksgiving Day parade,” the fourth and final investor proudly declares. “I made all my money from the big Charlie Brown!”

It’s exactly the kind of bizarre non-sequitur fans of the show’s first season are familiar with—a sudden, out-of-left-field swing that completely changes the rest of the sketch. And yet, while it may be predictable in that sense, there’s no way anyone would see it coming.

It’s not just a quick punchline, either—it rarely is with I Think you Should Leave. Instead, the faux show intro continues, with the Charlie Brown investor doubling down on her weirdness. “I still hate bald boys! I can’t stand bald boys!” she snarls. “When I see a bald boy, I think I’m back in the pants!”

Meanwhile, her fellow hosts are still tossing out cliches like, “Business is in my blood,” and, “I’m a wolf in the boardroom.”

It’s this delicate balancing act between the absurd and the mundane that I Think You Should Leave thrives on. Sketches frequently center on a lone person (usually Tim Robinson, but not always) making a situation uncomfortable and, rather than walking back their transgression, going so far into overdrive that it becomes hilarious. It’s the evolution of cringe comedy, pushing a simple awkward interaction into the realm of the bizarre.

“The Capital Room” is one of my favorite sketches of I Think You Should Leave’s second season, but frankly, the show offers an embarrassment of riches. There’s nary a dud in the first three of the season’s six episodes, and while I think the back half is a bit weaker, there’s still great content throughout.

The charm of the show lies in how baffling and unpredictable it can be; as a fan of the first season, I was spending my first watch-through of the second trying (and failing) to anticipate where the sketches would go. Which character is going to turn out to be the jerk? What’s the twist going to be? When will the punchline land, and how long will it be dragged out?

Here’s the thing, though: you’ll never guess it right, because the show doesn’t operate under any logic you can understand.

For a perfect example, look at the “Detective Crashmore” sketch from episode three. It starts off as a trailer for a hyper-violent, incredibly vulgar cop drama. For several minutes, the humor comes from how over-the-top the movie being portrayed is: it’s punctuated by constant gunshots and profanity from the foul-mouthed Detective Crashmore. It seems like that’s the joke—it’s just poking fun at how silly that style of action movie is, with some added humor derived from Crashmore’s lame one-liners.

Then we get to the “starring…” section and learn that Crashmore—who has spent all his screen time swearing and shooting people—is played by Santa Claus. And that’s not even the end of the joke! We’re then treated to an interview with Santa about the film, in which he rambles semi-coherently about cosmic gumbo and angrily starts to storm off when the interviewer mentions Christmas.

You’re probably having one of two reactions to these sketch descriptions: you either think they sound hilarious or insane. Either way, you’re right, and either way, you should go watch I Think You Should Leave.

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