Recently, Tim Robinson bought himself a gold watch. This shouldn’t have caused much of a problem: his sketch comedy series I Think You Should Leave debuted on Netflix in April of 2019, promptly became a surprise hit, and rocketed Robinson to prominence among the terminally online. The comedic veteran—who started at his local Second City before working his way up to Saturday Night Live—had become, all of a sudden, the kind of guy who might plausibly own a gold watch. But the moment he put it on, he ran into someone who disagreed and decreed, “That doesn’t fit who you are,” he tells me over Zoom.
Robinson wore the watch “out of pride” for a few more days, knowing the whole time that his conviction would fade. He’s since stopped wearing it altogether.
As he recounts this story, it’s hard not to think of a sketch from the second season of his show, which is now streaming on Netflix. The scene concerns the courtroom trial of two coworkers charged with insider trading, but quickly expands to include a third coworker—Robinson—who is wearing a sort of fedora with safari flaps. A lawyer attempts to read off damning text messages, but the conversation is constantly sidetracked by Robinson and his sad hat. Ultimately, his boss asks him to remove the hat, which he does before deciding to hit back. “I've never fought for anything in my entire life. I'm fighting for this hat,” he says defiantly. He then tries and fails to roll it down his arm like Fred Astaire before it gets caught under a wheelchair and covered in “wheel grease.” The scene is utterly humiliating. But Robinson’s sympathies remain with his bozo—and his own wrist. “I should be allowed to wear that watch,” he says, “just like he should be allowed to wear that hat.”
I Think You Should Leave is filled with characters like this, who share Robinson’s desire to avoid embarrassment. Crucially, unlike Robinson, nearly all of them are incapable of making the prudent choice that will save them from humiliation. “There are tons of ways people will try to manipulate themselves or lie, or different tactics they'll use to save themselves from being embarrassed or to save themselves from being the joke,” says Robinson. “We find ourselves fascinated with people digging themselves in holes to save face on something small that ended up making themselves look stupider.” It’s the idea, he says, “of tripping, and then your first instinct is to look back and be like, ‘What the fuck's wrong with this floor?’”
Robinson has made a career out of animating these micro-humiliations, first as a writer for SNL and now on Netflix. And while we’re able to laugh at his menagerie of idiots, someone has to spend all that time thinking about the anxious, embarrassing mundanities most of us are lucky enough to whiz past.
Which brings us to piss dots. Piss dots, for the uninitiated, are the small blotches of wetness that might appear on a pair of pants when a man wraps up at the urinal before he’s fully completed his job. I am new to the concept, and my naïveté comes as a shock to Robinson—as if everyone has spent at least a few hours of their existence fretting over piss dots. “Obviously, piss dots exist in the world and people get them,” he says. “They exist, yeah. I've had piss dots.”
But it doesn’t take Robinson’s confirmation to know that he is worried about piss dots, because they show up surprisingly often in his comedy. They’re a gag on Detroiters, the short-lived Comedy Central show about two goofy admen in Detroit that Robinson created with his best friend, the comedian Sam Richardson. They turn up again prominently in the second season of I Think You Should Leave, serving as the engine for one of this season’s longer and more experimental sketches. The bit concerns a website that sells pants with little dots already on them—they’re designed to help people get out of any and all piss dot-related jams. The site doesn’t actually sell the pants, though—the company claims to be always sold out, which “also makes it seem like it's a hot item,” Robinson’s character says. “It's the same thing Supreme does, wouldn't you agree?” The site is a front, Robinson’s determined middle-management type explains: if someone catches you with pee on your pants, you simply show them the website and that way they can’t prove what they’re seeing is piss. “It’s the perfect thing,” Robinson says in the show.
It’s clearly preposterous, and yet carries a whiff of the confessional. You don’t just happen to write multiple jokes in multiple projects across multiple years about piss dots if you haven’t spent a lot of time personally worrying about them. “We all can make fun of these things, but everybody has some version of it,” Robinson tells me. One man’s piss dots are another guy’s pit stains. This understanding makes I Think You Should Leave hilarious, and also a little miserable to contemplate.
Because, for I Think You Should Leave to be as funny as it is—and every episode in the second season made me laugh until I wept—Robinson needs to remain hyper-attuned to his neuroses. He needs to document the anxieties that accompany wearing a fancy gold watch, and also the ones that lead to an obsession with piss dots. The good news for us happens to be the bad news for Robinson: as the second season of his critically- and audience-beloved show drops, he is as anxious as ever.
Robinson put out the first season of I Think You Should Leave with what he describes as “pretty low” expectations, but the taut runtime—six episodes, none much longer than 15 minutes—was a labor of many years. Growing up in the suburbs of Detroit, Robinson loved sketch comedy. He’s especially come to appreciate the way that, unlike narrative television, characters can behave as badly as they wanted, without the consequences of those actions bleeding into the next episode or even scene. But it wasn’t until he attended a Second City show on a visit to Chicago that turning comedy into a career felt possible. “When you're young, getting a sketch on TV is unattainable,” he says. “But when I saw the live version, because it was there and in my face, it felt obtainable in some way.”
He returned home and joined his local Second City chapter, which grew into a gig in the troupe’s touring company, and then to a job at the mothership in Chicago. In 2011, he delivered a one-man sketch performance at Montreal’s Just for Laughs festival to an audience that included SNL writer John Mulaney, who recommended to the show’s producers that Robinson get an audition. He aced it, but after a difficult first year in the cast that involved sketches cut from television as he was acting in them or dropped just before he was about to take the stage, Robinson was told that he wouldn’t be coming back as a performer, although he could stay on as a writer. “That year was bad,” he told The Ringer. “Even if I felt good on a Tuesday, the depression was back again by Saturday.” Still, Robinson agreed to remain in the writers’ room, where he’d stick around for three more years. During that time, he met Zach Kanin, who would become Robinson’s co-creator on I Think You Should Leave. Some of the sketches from the first season date back to this time, as tiny little seedlings of ideas. (“That's been made a bigger deal than it is,” Robinson says of his turning SNL castoffs into Netflix sketches.)
The result of all this was one of the most riotous and penetrating works of comedy in years. It’s been difficult to navigate the internet over the past two years without bumping into one of Robinson’s buffoonish characters, like the guy in the hot dog costume who crashes his hot-dog shaped car through a clothing store window and then professes ignorance as to the culprit. There was the old man who loves bad car ideas and hates mothers-in-law; Steven Yeun as an unclean party host; and Richardson hosting a Baby of the Year competition that goes horribly awry. Always at the center was one of Robinson’s dopes. And though his characters all share certain qualities, he knows how to paint with every color of mortification: in one sketch, he’s the pained date caught in a lie, in another the teeth-gritted interviewee who refuses to admit he’s pulling a door that’s meant to be pushed. Robinson’s conventional appearance makes his inevitable turn to madness all the more striking.
The way these characters seeped into our modern, meme-ified language is perhaps the biggest sign of the show’s success. Robinson’s sometimes-repugnant characters became easy avatars for people and companies that exhibit equally gross or absurd behavior in real life. Minnesota representative Ilhan Omar twitter-shamed ExxonMobil with Robinson’s hot dog man, for instance.
I Think You Should Leave recaptures the magic of an earlier era, when sitting around yelling “I love lamp!” counted as a good time. Only now, we’re all hanging out on social media—and unlike Anchorman’s Brick Tamland, everyone knows what they’re yelling about.
Where the first season was a grab bag of nonsense, this year’s crop of sketches are a touch more thematically focused. “It's a lot of scams,” Robinson says. One sketch features the comedian (and one of the show’s writers) Patti Harrison playing an investor on a Shark Tank-style show. While we meet most I Think You Should Leave characters during the most excruciatingly embarrassing moments of their lives, we meet Harrison’s character after she’s been sewn into Macy’s Thanksgiving Day parade float. Now, she's scored a spot as a Shark after successfully suing the city over her troubles. She’s as shameless as every other I Think You Should Leave character—but, in a new twist, is seemingly better off because of it. It makes me think of the internet personality Caroline Calloway, who recently started selling skincare with the brazenly on-the-nose-name “Snake Oil.” I posit to Robinson that, in these sketches and real life, it appears that the scammers are now winning. “But they're not,” he says. “I'm not trying to get too deep on it, but even if these people are on top, they're not on top.”
Robinson might plausibly feel that he himself is on top. But despite all the success of the first season, it would go against everything he knows to feel confident about the second. “The confidence…” he says, “you’re never confident.” In conversation, the aggressive wide-eyed screamers he plays give way to a considerably softer-spoken character. Asked for his favorite sketches from the new season, he can’t think of a single one. “It's just a bad time to ask me right now,” deep in post-production, he says. He’s worried, of course, about the reception of the new season, but that’s just one ingredient in his anxiety salad. “I'm always anxious,” he says, tugging at his hair. “Always anxious at all times, but yes, it gets worse.” For Robinson, it’s “every part of it. Even doing this,” he says, about our interview.
Even as the show grows, Robinson still defaults to anxious. He was initially unsure about even doing a second season. Now, of course, he’s already worrying about whether he should do a third. “You're kind of catching me in that same headspace where these things are filled with anxiety,” he says. “There's so much anxiety attached to all this.” I feel guilty for adding to his stress—and then shamefully excited for the inevitable season three sketch featuring a sadistic interviewer who won’t stop asking an exasperated Robinson character about his process.
Robinson’s comedy is driven by characters squirming in awkward situations before doing whatever it takes to get out of them. And while his characters struggle to wiggle free, Robinson recently found himself in an unusually advantageous position. He had walked into a bar wearing a bright and colorful Nike jacket—so striking, and perhaps so out of character, that a man he’d just met decided to roast his fashion choice. Big mistake. Huge. Unlike the incident with his wristwear, Robinson wasn’t willing to back down so easily this time. Because what the man didn’t know was that the jacket was a gift from Robinson’s young daughter. A lesser man might have been embarrassed. But Robinson, like many of the characters he plays, refused his helping of embarrassment and decided to weaponize the gift. “Now I have a one-up on you: you're going to feel bad about saying that,” he recalls thinking. He shouted back: “My daughter gave me that!’” Sure, he was wearing a particularly garish jacket. But for the moment, at least, Tim Robinson had the upper hand.