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Ranking the Characters From ‘I Think You Should Leave’

Every sketch features a person who’s gone too far. Here are the most entertaining ones.

Netflix/Ringer illustration

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. (If you love the show and the NBA, boy do we have a niche Twitter account for you.)

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. It’s weird, wonderful, endlessly rewatchable nonsense.

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. 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. 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. 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. Let’s dive in.

29. Bart Harley Jarvis (“Baby of the Year”)

I HOPE YOU FUCKING DIE, HARLEY JARVIS!

28. The Whoopee Cushion Coworker (“Pink Bag”)

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 recipient of the “pink bag” (played by Robinson) first conveys genuine concern that he’s lost control of his bodily functions before turning on his colleagues because he can’t take—or it seems, understand—the joke. It’s one of the show’s weaker sketches, which would have benefited from being shorter or going on for so long that it loops back around to being funny again. (The sketch had five additional minutes trimmed from it; #ReleaseTheWhoopeeCut.) But Robinson wrings real tension out of the situation, ensuring that no one is ever going to think about pranking him again. And if you ever find yourself at the receiving end of a whoopee cushion, Robinson’s character is responsible for the best WTF clapback ever: “My farts are long, and way louder, and they REEK!”

27. The Horses With Micropenises (“Fenton’s Stables and Horse Ranch”)

Men who love riding horses but also feel emasculated by the size of a steed’s schlong have the perfect solution with Fenton’s Stables and Horse Ranch. You see, Fenton’s exclusively breeds horses with micropenises, thereby satisfying an insecure consumer base. (Tough beat for the horses, though.) This commercial parody is a bit lacking in the memorable character department, so let’s give a shout-out to the ridiculous sight of actual horses with tiny penis prosthetics, which I’ll merely link to rather than embed because I’m not trying to get fired.

26. The Babysitter Excuse Guy (“Babysitter”)

Who among us hasn’t come up with a fake excuse after being late to a social gathering? The problem for Robinson’s character in this sketch is that he backs himself into a corner by not just blaming a babysitter for his tardiness, but inventing a story that she was in a hit-and-run that wasn’t actually “a big deal” because she hit people who are “kind of like nothing.” The story doesn’t hold up under scrutiny, especially when a dude at the party named Barry keeps asking about it. And so, naturally, Robinson spends the rest of the party trying to exact revenge against him—a series of escalations that ends with Barry getting shoved into a china cabinet. Even though the night technically ends in violence, Robinson’s character is less intimidating than he is cringeworthy because of just how avoidable it all was. But his character’s ordeal does carry some important life lessons: Excuses are more questionable the more unnecessarily specific they get, and shoving a person into a cabinet at a party is, in fact, the worst possible way to deflect attention from yourself.

25. The Fake Gorilla (“Wilson’s Toupees”)

A hyperspecific infomercial for a hyperspecific problem: wanting to finally remove a toupee without the shame of your coworkers knowing that you were bald all along. Wilson’s Toupees offers 500 (!) increasingly balding wigs so that people assume you’re gradually losing hair over time instead of all at once. (If only this were a real product, it would’ve saved my friend Steve some trouble; sorry, pal.) But if for some reason you wanna lose that toupee sooner, the infomercial boasts a “Natural Fake Gorilla Attack Hair Removal System” that is, well, exactly what it sounds like:

Not all sketches need to convey a deeper meaning: Sometimes it’s just amusing to watch a guy get attacked by a gorilla. I also love the idea that having all your hair removed by a rampaging gorilla—who is so clearly a guy in a suit, he even did a wind-up punch—is a completely normal and valid excuse that friends and coworkers will buy into. Anyway, this needs to become a bit in Jackass 4.

24. The Guy Whose Head Was Humped by a Dog (“Lifetime Achievement”)

At an event celebrating the career of legendary pianist Herbie Hancock—tragically, not played by the actual Herbie Hancock—the presenter (Robinson) makes a quick remark before jumping into his speech that he doesn’t want a service dog euthanized for biting him. The problem is that the dog not only didn’t bite him, but actually humped his face after he tripped on his way to the podium. And it was all recorded on camera. Robinson convincingly sells his character’s desperation to save face: a humiliating situation that would’ve been avoided had he just let the humping incident slide in the first place. (Perhaps you’re sensing a theme.) The icing on the cake is that the humping culprit was a chihuahua, arguably the least threatening dog breed on the planet.

23. The Door Guy (“Both Ways”)

I Think You Should Leave’s first sketch sets the tone for the rest of the show with a simple scenario: A man (Robinson) leaving a job interview tries to pull on a push door, and instead of admitting to his mistake, keeps pulling until the hinges come off. The sketch’s effectiveness is really a testament to Robinson’s bizarre physicality, highlighted by the speck of drool dripping down his character’s chin as he finally fulfills the prophecy of the door opening both ways:

Screenshots via Netflix

Out of context, this grin would feel right at home in an Ari Aster film.

22. The Guy Who Doesn’t Wanna Admit He’s Choking (“Choking”)

In another sketch bolstered by Robinson doing the Absolute Most, he plays a guy who’s so afraid to embarrass himself in front of Caleb Went—a celebrity of sorts who has a super-hip clothing line—that he’d rather literally choke to death than call attention to himself. Of course, choking to death doesn’t work out for him, in both the physical sense (he’s slowly dying) and, perhaps more importantly, the fact that Caleb Went is totally weirded out by him. Robinson’s choking voice is the real winner here: a guttural, gasping-for-air gurgling that sounds like a duck learning how to talk for the first time.

21. Bozo Dubbed Over (“Bozo”)

A familiar plight in the internet age: What happens when you can’t think of a hilarious YouTube video to share with your coworkers? For Reggie (Robinson), the solution isn’t to find a viral video, but make his own by dubbing over old footage of Bozo the Clown. (Dubbing is actually a pretty successful niche on YouTube, from Bad Lip Readings of presidential debates to Yu-Gi-Oh! episodes.) The problem when Reggie presents it to his coworkers is that the video is nearly an hour long, has only a single view, and was obviously made by him. Reggie’s yearning for the approval of his peers is painfully recognizable—maybe we haven’t made an hourlong YouTube video about it, but we’ve all been in Reggie’s (clown?) shoes. And while “Bozo Dubbed Over” might not have been a winner in the workplace, I would definitely watch a video of Reggie dubbing over an Oscar acceptance speech while once again grumbling, “OH FUCK, I HOPE I DON’T JACK OFF!”

20. The Joyous Men From the TC Tuggers Commercial (“River Mountain High”)

What starts out as an impressive re-creation of a teen soap à la Riverdale soon descends into spon-con for a men’s clothing line. The sales pitch is initially delivered by the school’s principal (Robinson), who interrupts a couple teens to talk—for way too long—about the joys of TC Tuggers, “the only shirt that’s got a little knob on the front so you can just pull it out when it gets trapped on your belly.” But the sketch really soars when River Mountain High cuts to another impressive re-creation, this time a commercial with four middle-aged men having the time of their lives pulling on the patented belly knob. You could throw the TC Tuggers spot into a TNT ad break and nobody would bat an eye. The Tuggers’ (?) joy is as strong as my desire to buy a pair of TC Tuggers for my dad and uncle, who dress exactly like this foursome:

19. The Fully Loaded Nachos Guy (“Nachos”)

This sketch centers on a grievance that would feel right at home on an episode of Curb Your Enthusiasm: the unequal distribution of a shared appetizer. In this instance, Robinson goes on a first date with a woman who’s hogging all the fully loaded nachos. Telling your date to lay off the nachos is a mood-killer, though, so he thinks of the next best thing: asking the manager to make up a restaurant policy about reasonable nacho sharing. Unfortunately for Robinson’s character, he immediately gets called out on the lie, plans for a post-dinner movie are axed, and that second date is definitely not happening. But in my eyes—and probably Larry David’s, given his sensibilities—his heart was in the right place. Equitably sharing appetizers is a common courtesy.

18. The Guy Who Made a Shitty Mob Movie (“Baby Shower”)

Planning for a baby shower takes a drastic turn when Robinson’s character tries offloading props from an aborted mob movie, including black slicked-back hair wigs, Stanzo brand fedoras, and 1,000 tiny plastic meatballs. Robinson’s plight is immortalized in one of my favorite lines of the series: “I thought it was going to be a hit—it turns out it FUCKING SUCKS!” The quote is so memeable and versatile—I’ve definitely said it about the Washington Wizards re-signing Davis Bertans for $80 million and the final season of Game of Thrones. But the best part of the sketch might be Robinson’s character, a man so obsessed with prop wigs who also has a look that’s oddly reminiscent of Michael Showalter in Wet Hot American Summer: First Day of Camp.

17. Garfield Lady (“Party House”)

For the final sketch of I Think You Should Leave’s first season, Robinson cedes the spotlight to comedian Kate Berlant, playing a woman who offers to host a coworker’s intervention at her place. It soon becomes apparent that this is less about supporting a colleague and more about flexing that her house—supposedly purchased by Garfield creator Jim Davis—is covered head to toe in Garfield merch. The unhinged contents of the house threaten to steal the spotlight from Berlant, but when she interrupts the intervention to proudly point and whisper “all Garfield,” there’s no denying she’s the MVP:

16. Coworker Tracy (“New Printer”)

A new printer arrives at a nondescript workspace, which causes one office drone to say that Christmas arrived early this year, a joke so clichéd it’s a small miracle that anyone laughed at it. But laugh people did, and so one coworker, Tracy (an incredible Patti Harrison), tries to chase that high by attempting to retool the joke with increasingly bizarre innotations. (At one point, she tries out a Southern accent?!) It’s a basic sketch elevated by Harrison’s bonkers commitment and the relatable feeling of wanting your coworkers’ approval, because that’s Santa’s greatest gift of all.

15. Attorney Mitch Bryant (“Has This Ever Happened to You?”)

In a local law firm commercial that’d make Saul Goodman proud, Mitch Bryant (Robinson) looks like he’s going to rattle off the typical attorney spiel about getting compensated over an accident. (Cue the Cellino & Barnes theme.) But Mitch’s hypothetical becomes really specific: two exterminators taking turns using your bathroom, jumping on your couch during “Turbo Time,” and replacing your regular toilet hole with a tiny joke hole that’s just for farts. The more specific Mitch gets, the more loud and exasperated he becomes—by the end of the commercial I half-expected him to jump out of my screen like the girl in The Ring. It’s one of the show’s finest examples of Robinson’s distinct ability to turn shouting into a genuinely funny art form. And to answer Mitch Bryant’s question: No, it hasn’t ever happened to me.

14. Chunky (“Chunky”)

The person behind the costume had all summer to figure out what Chunky’s deal is on Dan Vega’s Mega Money Quiz, and completely shat the bed. At some stage of our lives, we’ve all pulled a Chunky.

13. The Instagram Caption Lady (“Instagram”)

I don’t have an Instagram, so I’m sympathetic to Brenda (Vanessa Bayer) when she misreads social norms—in this case, workshopping self-deprecating photo captions with a couple friends at brunch that take things a little too far. As in: “Slopping down some pig shit with these fat fucks, and I’m the fattest of them all.” Bayer’s oblivious, cheery delivery is what really sells the profanity, and if I Think You Should Leave is tempted to bring back characters in Season 2, I’d love to see Brenda navigating the wonders of TikTok.

12. Sloppy Mudpie Jacob (“Gift Receipt”)

As if there were any doubt that Steven Yeun is a jack-of-all-trades thespian worthy of his Minari Oscar nomination, he shows up in one of I Think You Should Leave’s funniest sketches as Jacob, a regular guy celebrating his birthday. Jacob’s birthday is going well until his buddy Lev (Robinson) senses that he didn’t like the present he gave him, and that he’s going to use the gift receipt to return it. To prove that he did like the present, Jacob consents to Lev eating the gift receipt, which immediately causes him to get really sick, which he then blames on the birthday boy for not using enough toilet paper after a Sloppy Mudpie (a euphemism for poop that been has permanently lodged into my brain). Rather than call out Lev for his seemingly irrational behavior, the party turns on Jacob when another partygoer doesn’t get sick eating a different gift receipt in a control experiment. Yeun elicits plenty of sympathy from the viewer as the straight man in the sketch whose birthday gets unnecessarily ruined, but that just makes the final twist even more satisfying: Jacob did, in fact, use too small a slice for his Sloppy Mudpie. It turns out Jacob is just as untrustworthy of Yeun’s character in Burning.

11. “Biker Guy” (“Biker Guy”)

A stereotypical biker exuding childlike glee at the sight of a motorcycle is amusing on its own, thanks to Robinson’s wacky appearance highlighted by torso-length hair and beard. But this endearingly stupid sketch reveals itself to be even weirder than its initial impression, since the dude describes a bike as a motorcycle with no motor and a car as two motorcycles with a little house in the middle. From that setup, it’s only appropriate that a Greyhound bus causes Robinson’s character to experience something between an existential crisis and an orgasm:

Robinson’s mannerisms over seeing mundane vehicles are so out of this world that it should come as no surprise that the character is actually an alien from a species that’s just, like, really into motorcycles. Woooaaahhh.

10. The Funeral Organist (“New Joe”)

One of the best sketches carried by a guest star, “New Joe” is a silly showcase for the late Fred Willard, who shows up as a replacement organist for a funeral. Instead of playing somber music for the occasion, Willard performs what amounts to a one-man carnival—complete with smashing plates, loud honking, and literal bells and whistles. These few minutes are a fitting encapsulation of Willard’s comedic genius at playing absurd scenarios totally straight, punctuated by his character saying to the mourners, without a hint of irony, “My condolences.”

9. The Honk If You’re Horny Guy (“Traffic”)

Conner O’Malley doesn’t have a ton of screen time across I Think You Should Leave’s first season, but boy does he make every second of it count. (He’ll feature again in this ranking, for good reason.) In “Traffic,” O’Malley plays someone driven to intense desperation after spotting a “Honk If You’re Horny” bumper sticker, taking the message as an invitation and trailing the car for over a full day. On paper, this sketch doesn’t seem particularly creative—its humor all comes down to O’Malley flailing around like his character’s life actually depends on whether or not he can satisfy his horny urges. But he more than delivers:

8. Charlie, Who Looked Like a Fool (“Which Hand”)

Could a magic act destroy a marriage? That’s how quickly the drama escalates in this date-night sketch when Charlie (Robinson) is made the butt of the joke during a magician’s act. Charlie shrugs it off, but his wife, Brenda (Cecily Strong at the top of her game), won’t let the disrespect slide, going so far as to say that, while they won’t get divorced until the kids are out of the house, she’ll make sure they don’t respect him. Strong’s wild commitment makes this sketch briefly feel like a Noah Baumbach movie, but it’s Charlie trying to stand up for himself at the magician’s next show—“I don’t have a boy dick!” he says with visible insecurity—that levels up the cringiness. The sketch’s last-second freeze frame is also the underlying message of Christopher Nolan’s The Prestige:

7. The Old Man on the Plane (“The Man”)

There aren’t many things more deflating than boarding a plane and realizing that you’re seated next to a person who’s clearly a bit off. That’s the crux of this sketch, which sees a honeymooning couple sharing an aisle with a man (Will Forte) who has a menacing air about him. (Not gonna lie, he looks like a creepy caretaker from a Scooby-Doo mystery.) The initial tone of the sketch implies that Forte’s character is planning something sinister, which is subverted in typically weird fashion: The man has held a grudge against Robinson’s groom since he was an infant who kept him awake on a flight to London years ago—an event that ruined his trip to his “beloved Buckingham Palace.” The man’s revenge boils down to wailing like a baby so his now-adult nemesis can’t get any shut-eye. Few performers can nail the pivot from scary to just plain silly like Forte, whose character suffers the ultimate indignity of being moved to his proper seat before takeoff—far away from the newlyweds. You hate to see it.

6. THE GHOST OF CHRISTMAS WAYYYYYY FUTURE (“Christmas Carol”)

The strongest endorsement I can give for this bombastic sci-fi parody/Christmas special is that Sam Richardson showing up in Amazon’s The Tomorrow War only made me think of his inspired work as the Ghost of Christmas Way Future:

I’m not even kidding when I say that Richardson showed more promise as an action star in these two and a half minutes than Chris Pratt did in that entire movie.

5. Jazz Connoisseur Howie (“Game Night”)

If we were ranking characters based on how good of a hang they’d be, Howie (Tim Heidecker) would belong in the seventh circle of hell along with Bart Harley Jarvis. When Howie spends time with his younger girlfriend’s friends and ruins their charades night by referencing deep-cut jazz legends like Marcus “The Worm” Hicks and Roy Donk, it’s like watching a slow-motion car wreck in the best possible way. Howie’s condescending tone—he tells his girlfriend she’ll never be a great writer because she doesn’t have a curious mind—is matched only by the relatability of his mood-killing antics. We’ve all had a friend date someone like Howie, and have counted down the days until they’ve broken up. Hopefully, unlike the characters in this sketch, it’ll happen before all the leftover, mild-temperature gazpacho soup is slurped up.

4. The Hot Dog Guy (“Brooks Brothers”)

In a contender for I Think You Should Leave’s most memeable sketch, a wienermobile crashes through the entrance of a high-end clothing store and leads to a bunch of confused customers wondering who was responsible for the incident, including … a guy in a hot dog costume (Robinson). It’s a perfect visual gag, but Robinson continues twisting the situation to make it even more deranged: His hot dog man is really insistent on the culprit having their bare butt spanked and, when the cops show up, he starts rattling off porn websites in a nonsensical soliloquy while not-so-stealthily trying to run away from the scene with a few fancy suits. “We’re all trying to find the guy who did this!” has resonated on multiple levels, including the realm of politics, which might say more about the sorry state of our country than Robinson’s actual aims for social commentary.

3. Robby Star From Superstar Tracks Records (“Laser Spine Specialists”)

As expected, a normal-looking commercial for spinal surgery takes a sharp left turn when one of the people endorsing the procedure, played by Robinson, declares that he and his rehabilitated back are going to finally confront the sketchy music producer who scammed him out of some money. That producer, Robby Star (the god Conner O’Malley), emits extreme Uncut Gems energy—from his wacky way-too-buttoned-down shirt to the fact that he exclusively speaks in all-caps to his sleazy attempts to wring more money out of Robinson’s character. (“I JUST GOT THIS NEW BEAT AND IT’S TOTALLY IN YOUR Q-ZONE, ALL RIGHT?”) I have been quoting Robby Star for the better part of two years, and countless rewatches later, I love how often O’Malley seems on the verge of breaking character before the camera cuts away from him:

Robby Star is timeless; Robby Star is a GUARANTEED GODDAMN HIT!

2. The Bones Are Their Money Guy (“The Day Robert Palins Murdered Me”)

This Walk the Line parody boils down to a contrast of styles between the cool Johnny Cash type (Rhys Coiro) coming up with a hit country song on the spot and his twitchy bassist (Robinson) blurting out a supernatural yarn about skeletons rising out of the ground and using their own bones as currency. The lyrical nonsense—“They’ve never seen so much food as this / underground, there’s half as much food as this”—is elevated by the constant look of dismay on Robinson’s face as the words spill out of his mouth. In the deepest recesses of his soul, he knows it’s a bad idea, but it’s too late to turn back:

Hang this image in the Louvre next to some bones (in the skeleton’s world, bones equal dollars).

1. The “You Have No Good Car Ideas” Guy (“Focus Group”)

“Focus Group” is emblematic of what makes I Think You Should Leave click. A Ford focus group begins with one chaotic participant (Ruben Rabasa) derailing the discussion with suggestions of a “good steering wheel that doesn’t fly off while you’re driving” and a car that omits space for mother-in-laws, and ends with the entire room turning on Paul (Zach Kanin), the sole voice of reason whose only crime is loving his mother-in-law. Rabasa is the ideal muse for Robinson’s unique brand of weirdness; the warped logic of his car ideas are as infectious as every one of the actor’s memorable line readings. “I doing the best at this,” Rabasa’s character says to Paul once he gets the rest of the focus group on his twisted wavelength, but he might as well be talking about his top-tier standing in I Think You Should Leave’s first season.