There are certain eras in the zeitgeist when one comedian reigns supreme, riding the cultural juggernaut wave. Think the Adam Sandler, Jim Carrey, Dave Chappelle, and Will Ferrell years. We’re currently living in the age of Tim Robinson, which given a media landscape as vast as pi, is impressive.
Whether you know him from his in-limbo Netflix series I Think You Should Leave, recent box-office success Friendship with Paul Rudd, current HBO show The Chair Company, or omnipresent memes, Robinson is synonymous with uncomfortable, original, and high-energy cringe comedy. From the recently launched Amy Poehler podcast, Good Hang, to OG WTF with Marc Maron, Tim Robinson is garnering acclaim as the surrealist creator, writer, and performer he is. As someone who always loves an awkward moment that isn’t mine, I find watching him to be like getting a customized gift from a comedian god who specifically crafted Robinson for my questionable entertainment.
There’s a Tim Robinson playlist on SNL’s YouTube page, where he was briefly a featured player and staff writer. His skits range from being a 6th grader on a date with an adult woman to an employee in an M&M factory with an offensive co-worker named Jim “The Bigot.” It’s the same humor that would’ve made me laugh at thirteen, but more evolved, multifaceted, and cultivated in the most juvenile way possible. Following his departure, the Detroit native, co-created a hometown namesake Comedy Central show Detroiters with Zach Kanin, also a former Saturday Night Live writer, and the two would go on to collaborate on I Think You Should Leave and The Chair Company.
Detroiters, the Comedy Central show about a fledgling Michigan ad agency, lasted two seasons, and a few years later, Robinson reemerged on Netflix with the sketch comedy show I Think You Should Leave – think Key & Peele and Portlandia, but with much more wincing and discomfort. His chaotic, unpredictable, and hyper-specific skits about seemingly mundane everyday scenarios are driving the show’s cult following.
Robinson is also one of eight comedians on Netflix Presents: The Characters. Individual episodes serve as a variety show for alternative sketch comedians. His skits have the same unrelentingly uncomfortable vibe as nearly all his work to date. So yes, on any given day, someone in my life is receiving a Tim Robinson-related meme.
Comedians Sam Richardson and Connor O’Malley are the Richard Lewis to Larry David or David Spade to Chris Farley for Robinson. Tommy Boy, the 1995 buddy comedy movie, depicts the average, joyous, shenanigans of a Spade/Farley collab, and anyone familiar with Curb Your Enthusiasm, the long-running HBO series that ended in 2024, appreciates the art of banter David and Lewis consistently delivered. Richardson, who co-stars in Detroiters, brings the shenanigans, and O’Malley the much, much, more unhinged banter. He also makes a brief appearance in Detroiters season 2 as Tim Cramblin’s brother Trevor, a man who rock-bottoms his stepdad (and rock-bottoming being a finishing move used by professional wrestlers in the WWE). Richardson and O’Malley also both play various characters on the Emmy Award-winning I Think You Should Leave.
Now three seasons in, fans are hopeful I Think You Should Leave will get a fourth, but right now, Robinson’s focus is on The Chair Company. It’s uncomfortably funny, showing how a single awkward moment can completely derail someone’s life. The series is grittier and a little more dramatic than his usual high-energy chaos, but it carries the same gracelessness. Unnecessary lies define his characters, moments that are both painfully relatable and deliciously cringey. In tone, The Chair Company aligns more with Friendship, where Robinson perfectly captures the absurdity of making new adult friends after 35, which, especially for men, means balancing raw vulnerability with unhinged humor.
Outside of comedy, Tim Robinson appears to be a chill midwestern guy. Based on social media and press interviews, he enjoys rooting for Detroit sports’ teams, skateboarding, posting anti-ICE memes, and looking for cool bugs to send in a group chat. He’s also a dad, but keeps his personal life separate from his professional public persona.
Social discomfort is uneasy, but somehow Robinson makes it laugh-out-loud, crying hilarious. Whether he’s doubling down on gauche behavior, embodying the confidence of stupidity, or running “a bit” longer than is appropriate – he makes you look, laugh, and recoil all at once.
Welcome to the era of the wincing cringe – it’s Tim Robinson’s world, and we’re all just uncomfortably living in it.
