When I Think You Should Leave With Tim Robinson premiered in 2019, it was like a breath of fresh air. Each episode of Tim Robinson and Zach Kanin’s sketch comedy series, co-written by John Solomon and produced by The Lonely Island, clocked in at under 20 minutes, and was packed with hilarious guest stars like erstwhile Detroiter Sam Richardson, alt comedy legend Tim Heidecker, and Saturday Night Live alums Andy Samberg, Will Forte, and Vanessa Bayer.
Every I Think You Should Leave sketch goes only as long as it needs to, with no filler. The jokes are quick and don’t pull punches, allowing things to escalate in the most dramatic ways possible. A man nearly pulls a door off its hinges in front of a potential employer. He chokes on a gift receipt to prove to himself that his friend liked the birthday present he bought. He makes a fake video so that he’ll have something to show his coworkers. Each centers around a social menace—often played by Robinson—who is both desperate to belong and unable to maintain even the guise of normalcy. This style of comedy is reminiscent of the character-driven studio comedies of the 1990s, popularized by the likes of Chris Farley and Adam Sandler. Much like these comedy legends, Robinson plays characters that have all the privilege necessary to succeed in society, but none of the social graces.
In season two of I Think You Should Leave, Robinson plays another collection of emotionally volatile male characters, all set off by the slightest inconvenience. Many of the sketches begin in mundane situations—baby showers, work meetings, birthday parties—heightened by Robinson acting as an agent of social chaos. A Robinson character takes everything personally and literally, barely able to function around other adults. He lies constantly, destroys property, and throws a tantrum whenever anyone tells him “no.” And even after being reprimanded, a Robinson character is sure to take away absolutely the wrong message.
These qualities are exemplified in season two’s opening sketch, where Robinson plays an office worker dismayed by having to attend a conference during lunchtime. He then puts his hot dog up his sleeve and tries to eat it covertly. Of course, everyone notices and before long, he’s choking on the hot dog in front of all his coworkers. Later, in episode three, the character returns in a commercial selling “hot dog vacuums,” a device that uses suction to pull out a hot dog while you’re choking. It’s no solution for the real problem (his inability to wait until after the meeting), but it is one for the problem he created for himself. Now, when he covertly eats a hot dog at his next job, he won’t choke again. Problem solved.
So much of the brilliance of the series lies in its ability to break social rules we didn’t even know we had. In the final sketch of the first episode, a man (Robinson) is told on a ghost tour that he is free to swear. Delighted, he begins to talk about cumshots and horse cocks. When the tour guide asks him to think more before he speaks, the man is confused: “I thought you said we could curse?” In episode three, a man (Robinson, again) watches helplessly as his former professor takes the food off his plate and eats it in front of him. Later in that same episode, Santa Claus nearly walks out of a junket after being asked about Christmas. Surly old men are a staple of I Think You Should Leave, giving each episode an injection of odd, masculine pathos. One sketch inserts an old man into a Claire’s ear piercing video, juxtaposing the sunny testimony of a little girl with that of someone much older, looking back on his unhappy life. Another has Bob Odenkirk playing a sad man who recruits Robinson into his delusions. There’s even a sketch that consists mostly of an old man dressed as Johnny Carson slapping people at a birthday party. Often these sketches feel like a twisted form of group therapy, as people are driven to their emotional limits by the chaotic men intruding on their gatherings.
But mostly, it’s a show about losing it, as Robinson’s characters succumb to their own insecurities, culminating in public spiraling. This is done masterfully in the final sketch of the second episode, where Robinson takes a baby’s rejection of him as an indication that the infant knows all about his past. This leads him to utter the season’s funniest line: “I’m worried the baby thinks people can’t change.” In another sketch, Robinson’s failed attempt to lighten up a party leads to a defiant declaration: “I’ve never fought for anything in my life—I’m keeping this hat.” Later in the season, a heated altercation in a parking lot leads Robinson to a shocking admission: He can’t actually drive and is terrified of his car.
The series’ guest stars also get their chance to go berserk. In one sketch, Richard Jewell’s Paul Walter Hauser plays a man who can’t even joke about hating his wife without being immediately filled with regret. In another, a mulletted Tim Heidecker heckles a comedian doing crowd work at a science fiction- styled bar. This season also treats us to the chaotic presence of writer and comedian Conner O’Malley, last seen on Hulu’s Shrill, appearing alongside his real-life wife Aidy Bryant. In sketches, O’Malley and Robinson act as a chaotic tag team, terrorizing everyone around them.
I Think You Should Leave also provides a showcase for another Shrill alum: rising star Patti Harrison. Harrison, who appeared in the first season, returns this year as a writer and performer, inserting her special brand of cringe comedy effortlessly into Robinson’s house style. Right on the heels of her Sundance success Together Together, Harrison continues to prove her comedic prowess, playing characters that rival Robinson in their strangeness and volatility. However, with the exception of Harrison, this season is lacking in noticeable female faces in comedy. But it does have Once Upon A Time in Hollywood… breakout star Julia Butters, who exhibits All That-worthy comedy chops.
Overall, season two of I Think You Should Leave is a touch on the somber side, leaning heavily into narratives about sad men who feel isolated from the world around them. It’s a show full of retro weirdos, obsessed with past glory days, casual male fashion, and seeming like a fun guy at the office. With this season, Robinson and Kanin have populated a modern world with 1950s sitcom characters—all scared, confused, and wondering how they got here.