Every Sketch From ‘I Think You Should Leave,’ Ranked

Cultural Critic


Earlier this week, the Emmy nominations were announced, and the funniest show of 2019, I Think You Should Leave, was shut out of the Outstanding Variety Sketch Series category. Some of the shows that were nominated (like Documentary Now and Drunk History) are quite good, while others seem like legacy choices (Saturday Night Live) or frankly don’t belong because they’re actually terrible (Who Is America?)

But none of them are nearly as “outstanding” as I Think You Should Leave, which is the most flat-out most hilarious sketch-comedy program since Chappelle’s Show. What gives? Perhaps it wasn’t nominated because I Think You Should Leave isn’t really in competition with other sketch shows right now. It’s only in competition with itself.

With that idea in mind, I decided to rank all 29 sketches from the show’s first season. Who is the most ticklish? Who is the most jigglish? Let’s find out!

29. “Traffic” (Episode 4)

Many of the biggest I Think You Should Leave partisans love this sketch. In terms of taking a simple idea — a guy won’t stop honking at a “Honk If You’re Horny” bumper stick — and pushing it to absolutely insane extremes, “Traffic” has much to admire. It’s certainly unpredictable, given that the sketch ultimately climaxes at a funeral. Plus, there’s a typically gonzo performance by Conner O’Malley, an always welcome presence in other Robinson projects like Detroiters and his excellent episode of Netflix’s The Characters. However … it goes on for a very long time and hearing that much horny car-horn is ultimately pretty grating. But while I don’t find “Traffic” funny at all, I can’t help but admire this show’s willingness to go big even on the thinnest of premises.

28. “Babysitter” (Episode 5)

Here’s another sketch that takes a simple idea — getting caught in a lie at a party, and then haplessly lying some more in order to cover it up — and fearlessly pushes it to surreal levels of extraordinary social inappropriateness. Digging beyond the bland niceties of human interactions to reveal the nightmarish anxiety that lies beneath is basically this show’s M.O., but I Think You Should Leave does it a bit more deftly in other sketches.

27. “Pink Bag” (Episode 2)

This sketch is basically a riff on why whoopee cushions aren’t funny. “Is that the joke? That I farted and nobody barfed?” is a very solid argument.

26. “Bozo” (Episode 6)

Like “Babysitter,” this sketch is about getting caught in a lie, only this time it involves a guy fabricating a black-and-white YouTube video of Bozo The Clown with dubbed over gibberish dialogue about jacking off. What other show presents an opportunity to type such an amazing combination of words?

25. “Lifetime Achievement” (Episode 4)

As a critic, it is my duty to describe I Think You Should Leave as a treatise on modern alienation and our collective shame at not measuring up to cultural ideals about masculinity, status, and wealth. But, honestly, sometimes you just want to see a dog hump a man’s head. Also: How exactly did the writers hit upon a lifetime achievement ceremony honoring Herbie Hancock as the setting for this premise? I’d like to think there were just looking for an excuse to use the line, “That’s why I love Herbie Hancock—he loves to lie.”

24. “Fenton’s Stables & Horse Ranch” (Episode 6)

R.I.P. Shortstack, a miracle of modern horse-breeding too modestly endowed to make it in this world.

23. “New Joe” (Episode 3)

One of the best parts of I Think You Should Leave is how it’s able to get spectacularly weird performances from special guest stars, whether it’s semi-regulars like O’Malley or ringers like comedy legend Fred Willard, who brings his charming middle-American guilelessness to the role of an organist who is way too jolly (and far too prone to smashing dishes) to play a funeral.

22. “Both Ways” (Episode 1)

The most underrated I Think You Should Leave sketch. As the opener of the first episode, it’s like an overture for the rest of the series. Robinson plays an awkward but essentially nice man who would rather almost pull a door off of its hinges than admit that he didn’t realize you could simply push it open. It’s both an extremely silly comedic conceit and a metaphor for the pitfalls of pride. Smart and dumb working in perfect tandem.

21. “Baby Shower” (Episode 6)

Whether this sketch works for you depends on if you find phrases like “Stanzo brand fedoras” and “1,000 plastic meatballs” and “50 black slicked-back hair wigs” funny. I, for one, happen to find them hilarious, as would anyone who would invest too much money in an ill-conceived mob movie.

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