Netflix’s I Think You Should Leave is essentially the kind of sketch comedy show that is made for hardcore sketch comedy fans. Created by former SNL cast member Tim Robinson and former SNL writer Zach Kanin, ITYSL is filled to the brim with sketches that range from the mundane to the bizarre.
Of course, peppered among all of the quality sketches are a few that while still hilarious, will make anyone watching them instantly feel kind of embarrassed for the characters. These are the 10 most cringe-worthy sketches from I Think You Should Leave.
“Babysitter”
This sketch is definitely cringe-inducing, but it’s going to sit at the bottom of the list for actually being one of the less funny sketches to be featured on the show.
After Robinson and his partner arrive late to a party, they decide to lie about the babysitter being late. Of course, Robinson takes the lie too far and vows revenge on the one inquisitive party member who won’t stop asking questions. It’s incredibly awkward, and not exactly the strongest example of how great this show’s humor can be.
“Bozo”
Everybody has been in a situation where they and their friends start trading off on funny YouTube videos. Everyone has a few up their sleeve, ready to go at a moment’s notice and good for a quick laugh. But what happens when it’s your turn to choose one, and you don’t actually have any ideas?
That’s the crux of this two-part sketch, where Tim Robinson’s character, lacking any ideas for funny videos to show his coworkers, decides to make one himself and pass it off as something he found. Unfortunately, the video in question (a clip of the old Bozo The clown TV show with an odd voiceover) raises too many questions that Robinson can’t seem to answer.
“The Day That Robert Palins Murdered Me”
There’s a scene in pretty much every biopic where the artist is in the recording studio and needs to come up with a new hit fast. Luckily, this always happens to be the exact moment that the artist writes their most famous song. In this particular sketch, that entire process goes a little bit sideways.
After a country singer implores his bandmates to follow his lead on a new, Johnny Cash-esque song. Unfortunately, his bass player (Robinson once again) takes this suggestion too far, turning the song into an odd treatise on the lives of skeletons and how they use their bones for money.
“Lifetime Achievement”
The best sketches on I Think You Should Leave start with an embarrassing moment and escalate it to an unbearably uncomfortable degree, before delivering the final beat to close things out. “Lifetime Achievement” fits this form beautifully, with Robinson once again playing a character trying to rise above his own incompetence.
The scene finds Robinson presenting a lifetime achievement award to musician Herbie Hancock, only to preface his speech by saying he doesn’t want the service dog that bit him to be put down. However, as time goes on, and Robinson draws more attention to the situation, it becomes clear that the dog was more interested in getting busy with his head after he fell down the stairs to the stage.
“Instagram”
This is the only sketch on this list that doesn’t feature Tim Robinson on screen, but his signature strange sense of humor is right there in the writing. Instead, the seemingly never-ending string of horrifying insults written in the style of a self-deprecating Instagram caption is delivered by Vanessa Bayer.
After her two friends post photos with captions like “brunch with these two dumdums,” Bayer takes it to the extreme, writing that she is “eating c*** with these sacks of s***” and “slopping down some pig s*** with these fat f***s and I’m the fattest of them all.” The sketch is gloriously profane and disgusting, but is really made special by Bayer’s chipper delivery and closing question to her horrified friends, “why are you guys bullying me?!”
“Baby Shower”
If there is one person you should never plan a baby shower with, it’s a guy who really screwed up in making his own gangster film. In the “Baby Shower” sketch, Robinson is with some friends planning what to put into gift bags for a baby shower. His suggestions include Stanzo brand fedoras, fake plastic meatballs, and 50 black slicked-back hair wigs.
As the suggestions get strangely more specific, the guy reveals that he is stuck with boxes of props for the aforementioned gangster film. After his friends relent, the guy takes it even further saying he has to sell them everything otherwise he doesn’t make a profit. At least one guy gets a kick out of the wig.
“Game Night”
This is one of those great sketches that inserts a truly rude, mean, and all-around annoying character into a normal situation. A woman is introducing her mature new boyfriend, who works at the tobacco shop her mom buys cigars at. As it turns out, the boyfriend, Howie (played as hilariously infuriating by Tim Heidecker), is kind of a jerk.
The trouble starts with a simple dig at the host’s record collection. Then, things get worse in a game of guess the celebrity, when Howie has loaded the hat with names like Marcus ‘The Worm’ Hicks, and the clues he gives to his girlfriend are all criticisms against her. Of course, even though Howie is the worst, as the pair leave, his girlfriend says to her annoyed friends, “you guys really embarrassed me in front of Howie!”
“Nachos”
Nachos are a perfect snack to share with someone, but what happens when one person is taking all of the nachos with the good stuff on them? Apparently, Tim Robinson’s character in this sketch thinks that he should have the host of the restaurant tell his date about a rule saying that one person can’t take all the nachos “with meat and stuff on them.”
Of course, Robinson’s date sees right through this ruse and immediately confronts him with all of the facts about this incredibly stupid plan. Watching Robinson fold under the pressure and unconvincingly dig himself deeper into his lies is so satisfying, especially when he realizes that the date is now over.
“Gift Receipt”
“Gift Receipt” is the sketch that keeps on giving. Featured as the final touch in the first episode of I Think You Should Leave, this sketch starts out with one embarrassing encounter, moves on to another, then takes a turn, and finally ends with a bizarre reveal and an untimely death. Yeah, there’s a lot going on here.
What begins as the social faux pas of asking to have a gift receipt back to ensure a gift is not returned quickly becomes an accusation of poor hygiene against guest star Steven Yeun. While it appears that Robinson’s accuser is the odd one out, the guests quickly turn against Yeun to see if the gift receipt (which Robinson ate, by the way) was tainted and cause Robinson to become sick. It’s a perfect distillation of the kind of humor this show has in spades.
“New Printer”
Finally, the sketch that takes the top spot for being by far the most cringe-inducing scenario possible is “new printer.” It’s one of those sorts of realistic scenes that could easily take place in anyone’s office, with one coworker trying to build on a lame joke about “Christmas coming early” and making it even lamer.
The hilarity of this sketch is delivered purely by Shrill’s Patti Harrison, whose every utterance of things like “Santa should have wrapped it” and “does that count as what I get for Christmas as my gift?” Her exasperation over nobody finding her jokes funny finally ends when Robinson’s coworker finds her yelling “Santa brought it early!” to be truly hilarious.
