20 of Tim Robinson’s Best (Non-ITYSL) Sketches

Photo-Illustration: Vulture; Photos: Documentary Now!, Getty Images, Netflix

A show as singular, beloved, and incessantly quoted as Netflix’s I Think You Should Leave doesn’t just materialize fully formed. It’s the culmination of years of hard work put in by co-creators Zach Kanin and Tim Robinson to develop their sketch sensibilities and sharpen their instincts. To put it in terms fans understand, it’s a prewritten country song that tells a coherent story. It’s not a hastily ad-libbed song about skeletons and bones and whether or not the latter are the former’s currency.

Much of this is a well-documented part of I Think You Should Leave lore. Prior to creating the show, Kanin and Robinson worked closely together at SNL from 2012 to 2016, collaborated on an episode of Netflix’s sketch anthology The Characters in 2016, then co-created, along with Sam Richardson, the beloved but prematurely canceled Comedy Central sitcom Detroiters, which aired from 2017 to 2018. Robinson has spoken about how some early I Think You Should Leave sketches were born from sketches rejected at SNL — a claim he later said was blown out of proportion in a GQ interview — and executive producer Akiva Schaffer first pitched Netflix on the series by pointing to Robinson’s episode of The Characters as a proof of concept. Other parts of Robinson’s oeuvre, such as the sketches he filmed for the Second City and Above Average, are less well known but offer similar glimpses at the voices, mannerisms, and comedic preoccupations fans of his work obsess over. With the third season of ITYSL premiering on May 30, it’s as good of an excuse as any to take a look back at some of his best sketch work outside of the show.

“We’re going to be capturing real reactions from people as Karl kind of messes with their day,” Robinson explains in ITYSL’s sketch “Prank Show.” Years before, he participated in this bus prank with his sketch group My Mans — which included Robinson, iO performer Mark Raterman, and Second City tour-company director Andy Miara — where the goal was similar: to capture the real reactions of people as he loudly broke up with his girlfriend over the phone, effectively messing with their commute if not their day. But there’s an impossible-to-predict twist here that pushes the whole experiment into much weirder and less obnoxious territory. Imagine a bizarre alternate universe where Robinson and Nathan Fielder morphed into one guy.

Robinson’s comedy journey began at the Second City. He quickly rose through the ranks at the theater’s Detroit location, rising from teenage improv student to touring-company member before moving on to Second City Chicago, where he filmed this sketch. Its core premise — a blooper show that has its own bloopers — is amusing if a bit thin, but Robinson extracts every last bit of mileage from it, proving that there is almost no scene he cannot enhance by getting into a screaming match.

A real sliding-doors moment in Robinson’s career. After watching this self-produced pilot Robinson made with his aforementioned sketch group, Comedy Central ordered a pilot from the trio that they later passed on. Would the world have ever gotten Detroiters or I Think You Should Leave if the station had picked it up? Maybe not. But judging by the sketches featured in this proof of concept, viewable in full here, Robinson’s specific brand of absurdity and controlled chaos would have lived on. Consider the very first vignette, which sees Raterman painstakingly putting on a pair of rollerblades before picking up a bicycle hidden out of frame then walking out of the room. As a bonus, the pilot features a certain Blues Brothers–inspired dance I Think You Should Leave fans will get a kick out of.

ITYSL may seem loose and spontaneous, but Robinson and Kanin have said explicitly they rarely let performers go off book. For a glimpse at Robinson’s true improvising chops, look no further than this scene he shot with fellow Second City alumnus Emily Wilson for Ted Tremper’s award-winning Vimeo web series. In it, the pair play a couple in the middle of a breakup talking through their dissolution. You can see the gears in their heads turning as they figure out which beats to hammer, and the scene really takes off the moment Robinson decides the reason he’s breaking up with Wilson is because he wants her to be more “conniving.”

This sketch is notable for being an early showcase of the easy chemistry between Robinson and his Detroiters co-creator, Richardson. At one point, Robinson says the line, “Saunders, you’ve said ‘cum’ an awful lot, and you know that,” which is also something someone should have said to his cumshot-obsessed character in the ITYSL sketch “Ghost Tour.”

Robinson’s rapport with Nasim Pedrad in this sketch, in which the two play a real-estate-agent husband-and-wife team pleading with the public to stop defacing their local advertisements, is remarkable. “We’re trying to find you a home,” Pedrad says. “Don’t muddy the experience by drawing the seed of man splattered on my face. That’s not fun!” Is the whole sketch just a flimsy excuse for them to say things like “seed of man”? Sure. But that doesn’t make me want to see an entire movie exploring the married life of this couple any less.

Here’s proof that Robinson was a fashion visionary long before he launched his iconic brands TC Tuggers and Calico Cut Pants. This shirt’s “Z” insignia isn’t that complicated of a pattern, but it does seem to thoroughly bewilder Kevin Hart, so maybe Dan Flashes could stock it after all.

One of three sketches in which Cecily Strong and Bobby Moynihan play retail workers who jump to the premature conclusion that they’re being fired during staff meetings and take the opportunity to scorch the earth and roast all their coworkers. Robinson stars in two of them as Carl, a seemingly good-natured older man whose happy-go-lucky energy is the perfect foil for Strong and Moynihan. “Oh boy, here we go,” he says enthusiastically when they finally turn their sights on him. He doesn’t get a ton to do here, but he makes the most of it, making Hart break repeatedly just by slumping his shoulders and nodding his head.

Before the Twitter account I Think You Should League Pass made a national pastime of contextualizing NBA headlines using fitting I Think You Should Leave stills, “Roundball Rock” foreshadowed this synergy. In this sketch, Robinson plays Dave Tesh, the lesser-known brother and accompanying lyricist of famous composer John Tesh, in a pitch meeting for the new NBA on NBC theme song. His proposed lyrics? An earworm for the ages. It’s a shame those troglodyte NBC executives couldn’t see the vision.

Robinson was one of a number of SNL affiliates who appeared frequently in sketches produced by Lorne Michaels’s digital studio, Above Average, in the mid-2010s. Here, he stars alongside Mike O’Brien and Shelly Gossman as a trio of porn stars who need more direction than their laissez-faire director (Conner O’Malley) is willing to give them. “Improvise a few lines back and forth and get straight to the sex,” he tells them. “Don’t overthink it.” Of course, they fail to heed this advice and immediately start inventing increasingly ludicrous backstories for their characters involving hate crimes, skyscrapers, and medieval castles. “The castle is not going to work at all,” O’Malley’s character says, pointing out the modern costumes and technology that clearly indicate a contemporary setting. “Baz Luhrmann bends those rules,” counters Robinson.

What starts off as a one-note joke about how much time a television clothes-shopping montage would take without the benefit of video-editing magic morphs into something much darker as Robinson’s character rejects every one of Mike O’Brien’s proposed outfits without explanation. “A part of me thinks that nothing you would have come out with I would have said ‘yes’ to,” Robinson says many outfits and several hours later. “Yeah, I started to get that feeling,” replies O’Brien. “Like it was about some control or something.”

In this, the first of three “Cream Brothers” sketches written by John Lutz, the former 30 Rock cast member and Robinson play a pair of determined but misguided brothers who launch a doomed ice-cream-truck business in the dead of snowy winter. The promotional ice-cream song they invent, which ends with Lutz’s character grabbing Robinson by the shoulders to calm him down, is very much worth the price of admission.

If the archetypical I Think You Should Leave sketch is built around a character embarrassing themself then worsening the situation by desperately trying to save face, this sketch from The Characters may be the blueprint for the whole show. In it, Robinson plays Sammy Paradise, a suave old-school crooner who seems to be cresting on an unstoppable wave of good fortune until he experiences precisely one gambling setback and his whole façade crumbles. “I’m a dead man!” he screams, before a series of disastrous attempts to climb out of this pit. A lot of Robinson’s characters make the mistake of doubling down, but this is his only sketch literally set in a casino.

“This year we’ve got the Pointer Brothers,” says a woman to her co-workers, remarking on the featured entertainment their company has booked for their work retreat. “Do they do Pointer Sister songs?” one asks. “I would assume so,” she speculates. “Anything else would be plain stupid.” But she could’ve never predicted how stupid.

Scott Aukerman and Schaffer teamed up with power-ballad superstar Michael Bolton to create this largely forgotten but entertaining Valentine’s Day special for Netflix in 2017. It was pretty nice of them to set aside three minutes of it just to let Robinson cook. Please accept this humble plea to get chef Roy, Robinson’s wisecracking, mind-reading celebrity-baker character, on an episode of The Great British Bake Off.

Quite possibly the most I Think You Should Leave sketch that has ever been on SNL, and Robinson isn’t even in it. He did have a hand in writing it, though — the dead giveaway being the moment Jason Momoa’s character decides to search for his daughter’s boyfriend (Beck Bennett), who has decided the best way to make a good first impression on his girlfriend’s parents is to hide convincingly somewhere in the house. “Make it fair, give us a clue!” Momoa says as a look of childlike wonder creeps over his face. “We gotta find this guy if we want to see what he looks like!” Credit to Momoa for perfectly matching the energy of the completely unknown actors Robinson gravitates toward casting on I Think You Should Leave.

Putting a full Documentary Now! episode on a list of short sketches feels a bit like cheating. But if there’s ever been a person Robinson was born to spoof, it’s professional bowler Pete Weber, best known for getting too amped up after bowling a climactic strike on TV and screaming, “Who do you think you are? I am!” Here’s his character Rick Kenmore’s riff on this famous outburst: “Who’s the man of the day? I am! You guessed it! Why not? Who knows? I do! Never, never talk to me about before! This guy is! Me! That’s how I know! You know! Suck my sack!” Naturally, the latter becomes Kenmore’s catchphrase.

This sketch has a lot working against it. Part of a promotional campaign the legendary record label Sub Pop participated in to promote voting in the 2020 presidential election, it takes place on Zoom, instantly recalling the horrors of pandemic-era entertainment. Against all odds, it has stood the test of time. Robinson, as band manager Frank Schøttendt, is confident that the missing ingredient in the Postal Service’s live show is his 18-person band filled with “roughnecks” who don’t get along with each other. Unfortunately, despite the urgency he conveys by sitting way too close to his camera, the band is not sold. It’s their loss! “Mike Steaks,” in spite of being a bully, can really shred.

The first clue Robinson wrote this sketch? The name “Jack Flatts.” It’s a perfect Robinson-ism, a clear brainwave from the mind that brought the world “Tammy Craps.” The second clue? The sketch, about a group of desperate men who are irate that their favorite restaurant, “where the waiters make fun of you,” is not open at the height of the pandemic, is a clear offshoot of this bit Robinson did on Tim Heidecker’s podcast Office Hours earlier in 2020 in which he complains on the local news that COVID-19 restrictions are stopping him from buying his “Halloween stuff.”

Robinson is a skateboarding enthusiast who knows his way around a board, so it was only a matter of time before his two passions collided. In this promotional video he filmed for the California-based clothing brand Brain Dead, he plays the manager of a skate team featuring a new member named “Concrete Halloween” who skates in a monster mask, “goes as fast as he can toward curbs with no trick in mind,” and used to be an executioner but “got fired because he kept laughing and fucking around during the deaths.” The world must have this guy as a playable character in the next Tony Hawk’s Pro Skater game.