Tim Robinson has had a big year between his new show The Chair Company (2025) airing on HBO Max and the film Friendship (2025) releasing in theaters and on streaming. The comedian, who started out as a cast member on Saturday Night Live (1975) before really breaking out as creator and star of his own shows, is best known for his absurd, awkward, often cringeworthy sense of humor.
No one does cringe comedy quite like Tim Robinson. And while the genre isn’t everyone’s cup of tea, Robinson’s work is perfect for those who find humor in social faux pas and uncomfortable situations. Whether you’re a fan or just enjoy things that make you laugh and squirm, this list will rank Tim Robinson’s comedies by how uncomfortable you’ll probably be watching them, as well as where to find them on streaming services like HBO Max and Netflix.
5. Saturday Night Live (1975-Present)
Tim Robinson started out as part of the Saturday Night Live cast, appearing as a featured player in Season 38 and working as a writer for Seasons 39 through 41. Sadly, Robinson never really got to shine on SNL, with his only recurring character being an elderly man who gets verbally abused by Bobby Moynihan and Cecily Strong. There are a few sketches where his signature humor shines through, including “Z-Shirt” with Kevin Hart and “Real Estate Agents” with Nasim Pedrad and Joseph Gordon-Levitt, the latter of which was unfortunately cut short due to the live nature of the show.
Everything Robinson has done in the past decade has made it clear that his unique brand of humor just wasn’t a good fit for SNL. As someone who watched the show religiously in that era, I’m thrilled to see Robinson thrive in movies and shows where he can embrace the cringe. If you want to see where Robinson started out, though, check out his SNL work, just don’t expect these sketches to be as outrageous and weird as his newer material.
4. Detroiters (2017-2018)
Underappreciated sitcom Detroiters is about two best friends who make low-budget ads for local businesses, pairing Tim Robinson with real-life friend and fellow Detroit native Sam Richardson, best known for his role on Veep (2012). Tim and Sam—the characters, not the actors—might not be good at their jobs, even if they think they’re Don Draper in Mad Men (2007), but they make up for that with their clear love for each other.
Detroiters is more absurdist than cringe, which is why it’s ranked low on this list. But that certainly isn’t a reason to not watch the show. If anything, the difference in humor and tone means it should appeal to a wider audience than Robinson’s more niche projects. If you like quirky, off-kilter comedies like Community (2009) and Nathan for You (2013), give Detroiters a chance. You’ll probably end up among the many, including Seth Meyers, who think the show deserved more than two seasons on Comedy Central.
3. I Think You Should Leave with Tim Robinson (2019-2023)
Tim Robinson may have been underutilized on SNL, but I Think You Should Leave with Tim Robinson makes it clear that he’s great at sketch comedy. What the show lacks in connective tissue or overarching themes—other than people acting inappropriately or being confidently wrong—it makes up for in bizarre humor, a fantastic lineup of guest stars, and quotable moments.
I Think You Should Leave is absurdist, silly, and occasionally insightful in a way that fans of The Lonely Island will recognize. (Andy Samberg, Akiva Schaffer, and Jorma Taccone are actually executive producers on the show.) It certainly excels in the cringe department, though the nature of sketch and the series’ short episodes mean it’s not quite as uncomfortable a watch as other Robinson comedies.
2. The Chair Company (2025-Present)
Robinson’s newest show is just getting started, but The Chair Company already looks to be another hit. It follows a man named Ron Trosper (Robinson) who begins obsessing over a chair manufacturer after an embarrassing incident with a defective product, only to discover there’s a vast conspiracy to investigate. Simultaneously a comedy, thriller, and horror series, The Chair Company turns the kind of persistently loud character Robinson is known for into a relatable character you can root for by presenting him with real stakes and a compelling mystery.
The Chair Company shares the same kind of divisive humor as other Robinson comedies, though it mixes it with more explicit social commentary, diving into issues of mistrust and isolation in the digital age. If you enjoy thrillers that leave you thinking like Severance (2022) and can handle heavy doses of cringe comedy, give The Chair Company a watch.
1. Friendship (2025)
Nothing was going to top Friendship as the most uncomfortable Tim Robinson comedy yet, and I say that as someone who loves this movie. In his first lead role in a feature film, Robinson plays Craig Waterman, a lonely and socially awkward man whose friendship with a new neighbor (Paul Rudd) turns into unhealthy obsession and a dramatic downward spiral. While it’s billed as a dark comedy, I’d describe Friendship as a horror movie where the monsters are uncomfortable social situations and the jump scares are shifts in tone so sudden you’ll feel the whiplash.
But while it’s an incredibly awkward movie full of the cringe comedy Robinson fans expect, Friendship is also a powerful statement about loneliness and the challenges of making friends, especially for adult men. Stay far away from this movie if cringe comedy isn’t your thing, but for me, Friendship is the most I’ve ever enjoyed feeling completely uncomfortable.
