As social media probably reminds you every time you look at it, the second season of I Think You Should Leave with Tim Robinson came out on Netflix earlier this week. The sketch comedy’s first season was a word-of-mouth hit in 2019, gradually turning into one of society’s more prolific meme factories as more and more people discovered it and Robinson’s idiosyncratic approach to comedy. If the first season’s ascent to meme godhead was a slow burn, season two’s was a supernova; within minutes of its 3 a.m. ET release, Twitter was already full of screenshots, GIFs, and references. Who knows how many actually watch the show—Netflix keeps those numbers locked up tight—but it’s undeniable that Robinson and his show is a viral sensation, and a well-earned one, after over a decade of working in the comedy trenches.
If you’re a I Think You Should Leave superfan who is somehow unfamiliar with Robinson’s earlier work, well, let us help fill in those gaps. Many of Robinson’s collaborators from I Think You Should Leave have worked with him throughout his career, notably including co-writer Zach Kanin and actors Sam Richardson and Conner O’Malley. Robinson and his colleagues have constructed their own weird but instantly recognizable little comedy world over the last decade plus. Hopefully you’ve heard about Detroiters by now; if not, read on, and learn about that and a few other Robinson projects you need to watch.
Originally on Comedy Central
Now Streaming on Paramount+
Let’s move backwards through time. Robinson’s most prominent project before I Think You Should Leave was Detroiters, a fantastic sitcom that co-starred Sam Richardson and ran for two seasons on Comedy Central. We’ve written extensively about Detroiters here at Paste, and every word of it is as true today as it was when it was published. Detroiters packed the absurdity and embarrassment you expect from Robinson into the sitcom format, while also presenting one of the sweetest and strongest male friendships seen on TV. As a sketch show I Think You Should Leave is fragmentary in nature, with many sketches ending abruptly; Detroiters proves that Robinson and his co-writers Richardson and Kanin can maintain their instantly recognizable comic voice in a longer-form narrative.
Streaming on Netflix
Netflix’s eight episode sketch experiment from 2016 is very hit or miss. That’s baked into the concept, though; each half-hour episode spotlights a single comedian, with little repetition or crossover between episodes. Robinson’s episode is the best, and is the closest thing to I Think You Should Leave you’ll find on this list. You could almost view it as a pilot for that later sketch show; Robinson co-wrote it with Kanin, who appears alongside O’Malley in a corporate retreat sketch. If you haven’t watched Robinson’s episode of The Characters, you’re basically missing out on one-and-a-half episodes of I Think You Should Leave. Any sketch from this episode would fit perfectly into the later series.
Years: 2012-2013; writer from 2013 to 2017.
Streaming on Peacock and YouTube
Robinson had a weird stint on SNL. He debuted as a featured player in the fall of 2012, and after that one season he left the cast and was transitioned to the writing staff. During his one season in the cast he fell into a standard role all too familiar to SNL viewers—he was one of those cast members who almost never makes it onto the air. He did star in at least two sketches that bear the hallmarks of his writing, though. The more famous of the two, “Roundball Rock,” co-starred future Detroiters producer Jason Sudeikis, and features an unhinged Robinson performance right out of I Think You Should Leave. He also co-starred with Kevin Hart in one of the very few SNL sketches to actually break the show’s staid format; even though Hart doesn’t make it all the way to Z in the pretaped commercial parody “Z-Shirt,” there was no reason to think the gag would be continued in the live sketch ”90’s Funeral.”
Unaired Pilot for Comedy Central
Now Streaming on YouTube
Before SNL, Robinson came up through the Chicago improv scene, performing at both The Second City and iO Theater. He was part of a comedy team with Mark Raterman and Andy Miara, performing under the name My Mans; with the help of Bob Odenkirk, they got a deal for a pilot with Comedy Central, and you can see most of that pilot today on YouTube. The network passed on the pilot (because why would Comedy Central want to air good comedy?) and in less than a year Robinson was working on SNL. Raterman later showed up in an episode of I Think You Should Leave.
Outside of his major projects, Robinson has popped up in all manner of TV shows and YouTube videos. Here’s a quick rundown of some of the more notable ones.
In 2015 Robinson and Mike O’Brien wrote and starred in an excellent short for Above Average called “Unique Hospital: The Surgery Results.” It costars Amber Ruffin and Laura Grey and I don’t want to say any more than that because you need to let this one just unfold for you on its own. It’s up there with The Characters in terms of how perfectly it would fit into I Think You Should Leave.
Early in Seth Meyers’ run on Late Night, Robinson made a handful of appearances as Dale, an emergency sidekick brought out whenever Meyers needed his own Ed McMahon. The first couple minutes of this video from 2014 are basically setup, with an intentionally lame and unfunny late night bit leading up to Robinson taking the spotlight for his expected brand of discomfort.
Last year Robinson was one of several comedians who appeared in an original video promoting The Postal Service’s “get out the vote” campaign. It’s a callback to a similar video the band made almost a decade ago, only now done entirely through Zoom. Thankfully they released Robinson’s entire video as a standalone on YouTube; it’s over six minutes long, and although it’s very shaggy, it’s still hilarious.
Senior editor Garrett Martin writes about videogames, comedy, travel, theme parks, wrestling, and anything else that gets in his way. He’s also on Twitter @grmartin.