"One reason Robinson’s sketches feel so fit to the political moment is that so many of them are about the violation of norms," says James Poniewozik. "What happens if you just decide to brazen your way out of situations by lying and counterattacking and daring people to point out your hot-dog suit? Why admit defeat when you can declare victory? (That this usually turns out badly for Robinson’s characters may be the show’s most optimistic aspect.)" In Season 2, Poniewozik adds, "the new episodes don’t feel tired, because there is no shortage of ways to overstep social boundaries... The new season is as bizarrely funny as the first, but it can also shade bittersweet, even poignant. Over and over, the sketches find a twisted path to pathos, whether the subject is a man on an 'adult' haunted house tour, confused and hurt that his obscene questions about ghosts’ habits are ruled out of line, or a sad-sack community-theater actor tormented by a scene partner who steals his lines." Poniewozik adds that I Think You Should Leave is more than blisteringly funny. "The most resonant TV comedies identify types of conflicts and characters that we may not even have realized existed," says Poniewozik. "This was practically why Seinfeld was created; it seems there’s a Simpsons reference for just about every human foible. And Robinson, who created the series with Zach Kanin, has given us That One Weird Guy served up dozens of ways. The characters populating his sketches are midlevel drones in chinos and novelty shirts who haven’t completely grown up. They have unrealistic ideas of their abilities and how the world works. (Many sketches have the rambling momentum of a preschooler’s story, such as an injury-lawyer commercial that spins into a tale about a man bullied by exterminators who install a novelty toilet in his bathroom.) They have the childlike belief that if they deny reality, they can change it. They don’t read social cues well. They try too hard to be liked. They nurse weirdly specific grievances. They feel pressure to be confident and tough, and it scares them. They break rules, yet are obsessed with what is and isn’t 'allowed.' They get mad. They get really mad!"
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No show embodies our "Main Character Syndrome" like I Think You Should Leave: Tim Robinson's Netflix series is, says Craig Jenkins, "a show about the kinks in the human condition, about the desperate thoughts and feelings we bottle and the odd behaviors we hide in order to look and sound just like everyone else. We all keep up appearances. We curate cool, affable public selves for the benefit of seeming more agreeable to friends, co-workers, and onlookers to avoid arousing suspicion. The goal of a day online is never to be the 'main character.' Offline, it’s to stay away from the business end of a camera phone recording a viral video. Attention is nice, but scrutiny is not; we pursue the former and evade the latter. Success is no one noticing this struggle, no one grasping how much of our self-worth is tied up in this elaborate theater of niceties. I Think You Should Leave is a world where everyone sees every gear turning, every bead of sweat trickling down your forehead, in 4K. Just as The Twilight Zone tells us stories about people slowly coming to painful realizations that science (or magic or spirituality) is less predictable and more dangerous than they’d been led to believe, I Think You Should Leave teases a subtle horror out of everyday people bombing exquisitely as they attempt a high-stakes performance of normalcy in public."
What is so mindblowingly delightful about I Think You Should Leave is how it takes frequent turns down the lesser-travelled route to hilarity: "Tim Robinson looks like any old generic, middle-aged American white guy you might see shopping the aisles of Walmart or chugging bottled beer in a sports bar, while cheering on the Cincinnati Bearcats," says Ellen E Jones. "That’s a kind of superpower for a sketch comedian. In fact, he’s the aberrant talent behind I Think You Should Leave, the breakout sketch comedy hit of 2019, now back on Netflix for a second season." Jones adds: "I Think You Should Leave is among the freshest and funniest TV comedies of recent years, but it isn’t that the premises are particularly innovative – pop culture parodies, office etiquette and bad dinner dates are all mainstays of sketch comedy. Its style of humor, while frequently labelled 'wacky' or 'out there,' also isn’t so far out that its lineage can’t be traced – indeed, Mr Show’s Bob Odenkirk and Tim & Eric’s Tim Heidecker both guest star. Yet most comedy that dares to stray from the beaten track does so at the risk of getting lost in the weeds. Fans learn to accept a certain hit-to-miss ratio. What is so mindblowingly delightful about I Think You Should Leave is how it takes frequent turns down the lesser-travelled route to hilarity, and unerringly reaches its destination. In good time, too: most episodes come in around the 16-minute mark."
I Think You Should Leave homes in on the elements people loved about the series in Season 2, rather than any specific characters or setups: "If the show can be said to have anything like a formula, it’s this: Something in the world of the show is always going tremendously, catastrophically awry, but everybody treats it like just another one of life’s little quirks," says Joe Berkowitz. "Maybe they even come to embrace it. Contrary to the title, people in each situation tend to take great pains not to kick out whomever is making things weird, but instead offer every chance for them to hang around. Nobody is beyond redemption in this world, because nothing really matters. It’s an ideal antidote to the actual world, where everything is always breaking down but the stakes couldn’t be higher."
I Think You Should Leave is weirder and more ambitious in Season 2: "Season 2 keeps those grand curveballs coming," says Ben Travers. "Maintaining the 15-to-17-minute episodes and bringing back many favorite guest stars (Sam Richardson, Patti Harrison, and Tim Heidecker among them), I Think You Should Leave still bucks expectations with every new sketch, while stretching its structure in refreshing new ways. One episode features a nine-minute sketch — nine minutes! — and it comes soon after an opening short (featuring Paul Walter Hauser) that’s so sweet and innocent, I’m not sure it’s meant to be funny. Similar questions of tone and intent pop up in the first episode, when Tim plays a prank comic whose inhuman latex disguise sends him spiraling into depression (though there’s still an unmistakably hilarious closer)."
I Think You Should Leave is more chaotic and somber in Season 2: "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," says Jourdain Searles. "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."
The best compliment you could pay about I Think You Should Leave Season 2 is that it doesn’t feel like a Season 2: "This is not the same crew trying to recapture the magic of what made their first season so great. Instead, it feels like a Volume 2 – it’s simply more original, insane comedy sketches that are uproarously funny," says Adam Chitwood. "Save for one exception, none of these sketches try to revisit territory covered in the first season, and the one that does – while admirable and understandable – doesn’t quite hit the mark the same way its predecessor did."
Corncob TV's "Coffin Flop" reality show could actually happen in real life: "This is dumb humor, and it is hilarious, but 'Coffin Flop' also manages to make some points about certain kinds of reality TV shows and how they’re produced," says Andy Dehnart of Season 2 sketch. "Let’s be clear: I completely lost my sh*t—crying and hyperventilating— while watching this not because of the satire or cultural commentary, but because of the shock value of the footage: body after body falling out of coffins. One rolls down a hill, another falls out of the back of a hearse. At one funeral, a kid is knocked over backwards with surprise."
Keegan-Michael Key recalls being one of Tim Robinson's first improv teachers at Second City Detroit: Key remembers Robinson as “an extremely eager student, always wanted to push, always wanted to figure out a little more.” Key adds: "He’s very adept at playing that weird guy at the bus stop. But what makes him special, this ineffable quality he has, is that he really believes his point of view, and he doesn’t understand why you don’t understand his point of view. As opposed to, Your opinion be damned. He wants the other people in the sketch to understand where he’s coming from, but they don’t. It heightens it in a worse and worse way. That’s one of the qualities that I remember seeing in Detroit.” Like everything Robinson has done, I Think You Should Leave is born out of unease, the source of his comic genius -- which is why he couldn't imagine doing SNL now, at age 40. “As I’ve gotten older, my anxiety has gotten so much worse. I don’t think I could go on live TV,” says Robinson. “Just the spinning out of ‘You’re on live TV right now’ would freeze me up.”