10 Movies To Watch If You Love HBO’s The Chair Company
10 Movies To Watch If You Love HBO’s The Chair Company
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10 Movies To Watch If You Love HBO’s The Chair Company

🕒︎ 2025-11-09

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10 Movies To Watch If You Love HBO’s The Chair Company

HBO's The Chair Company is taking cringe comedy to new heights, and there are a slew of hilarious movies to watch after enjoying the brilliant series. Co-created by Tim Robinson, the series is yet another triumph for the outsider comic. Exploring Robinson's absurd approach to humor on a larger scale, The Chair Company is the most original comedy in years. What the show does so well is introduce seemingly normal situations and push them to their most ridiculous limits, and each episode builds the cringe-inducing suspense. Though Robinson has perfected the style in shows like I Think You Should Leave, the ongoing narrative of The Chair Company is one of the things that makes it such a unique experience. Plenty of movies have done the same thing, and there are a host of standout films that match the tone of HBO's latest hit series. While the content might differ, there are some films that are filled with hilarious embarrassment and goofy shenanigans that will keep viewers laughing after they've caught up on episodes of The Chair Company. Drop Dead Gorgeous (1999) Despite middling reviews, Drop Dead Gorgeous is one of the best comedies of the 1990s. The mockumentary concerns the contestants of a regional beauty pageant, and the absurd lengths some will go to win. With a cast of young stars like Kirsten Dunst and Brittany Murphy, the movie is very of the moment. Though the approach is wildly different, Drop Dead Gorgeous captures the same embarrassing sincerity that The Chair Company does. Both the movie and show borrow from the playbook of a thriller film, but they do so with cringey laughs. The cult classic had a clear influence on future comedic projects. After Hours (1985) Though Martin Scorsese is best known for his dramatic films, he's no stranger to comedy too. After Hours follows a bored workaholic who, through a series of unfortunate events, spends one crazy night in the city. Mixing farce and cringe, After Hours is a radical addition to the '80s comedy canon. Like The Chair Company, After Hours exploits relatively mundane situations for absurd comedy and huge laughs. Each moment builds upon the next in a rising series of unbelievable twists, and Scorsese is uniquely skilled at making the audience squirm in their seats. The fast-paced thrill-ride isn't just exhilarating, it's hilarious too. Brian And Charles (2022) Jim Archer's oddball buddy comedy film, Brian and Charles, largely went unnoticed, but it's well worth a revisit. A lonely man living in rural Wales builds a robot companion that opens him up to new life experiences. Keeping the cringe to a minimum, Brian and Charles gets laughs by being charming and goofy. There is a one-of-a-kind quality to Brian and Charles that will appeal to fans of The Chair Company. The humor comes from a different place, but both embrace the wild spirit of new comedy styles. The 2022 indie flick has a heartwarming vibe, yet it doesn't skip out on the funny moments. Shiva Baby (2020) Rachel Sennott should have won an Oscar for her comedic turn in Shiva Baby, and the movie deserves a lot more attention. While attending a funeral, a young woman finds herself in a series of awkward situations as her life converges on the event. Emma Seligman's understated comedy is hilarious in a subtle way, but very cringe-inducing. Taking a page from classic mumblecore movies from the Aughts, Shiva Baby thrives on its own awkwardness. It's quiet and contemplative when compared to The Chair Company, but just as awkward. There's also a lot of substance to the story, and it's an exploration of the foibles of young adulthood. The 40-Year-Old Virgin (2005) Helping to crown Judd Apatow as one of the kings of Aughts comedy, The 40-Year-Old Virgin remains an all-time classic. A worker at an electronic store is forced into the world of dating when it's revealed he's a 40-year-old virgin. Steve Carell gives the performance of a lifetime, and he excels at playing a likable underdog in a weird situation. The Chair Company is the opposite of The 40-Year-Old Virgin, where the main character is the oddball in a normal world, but the result is the same. The 2000s gem has plenty of cringe moments, but also has the slick production and accessible feel of an Aughts comedy. The 40-Year-Old Virgin is the best of both worlds. Lost In America (1985) Albert Brooks directed a handful of extremely underrated comedies throughout his career, and Lost in America was his best effort. A yuppie couple decide to cash out and go on the road, only to hit one speed bump after another. The '80s cult classic brilliantly skewers the decade's culture, and the Baby Boomer generation in general. By making the main characters so relatable, Lost in America is all the more hilarious when everything goes wrong for them. The cringe comes from a series of earnest, but poor decisions, which is reflective of the tone of The Chair Company. However, Brooks' approach to comedy is much more droll and understated. Death At A Funeral (2007) Frank Oz' Death at a Funeral was completely overlooked when it premiered in 2007, but it is now revered as a modern comedy classic. When one of the family members dies, a dysfunctional clan is brought back together and things fall apart immediately. With so much going on, Death at a Funeral never takes its foot off the gas. In classic farce fashion, every scene is packed with mishaps and embarrassing moments that give the viewer second-hand cringe. The bombastic comedy makes The Chair Company look tame by comparison, especially since every moment has a goofy and heightened sense of reality. It has no message, but the laughs are what matter most. Best In Show (2000) Christopher Guest's ensemble comedies are deft at using cringe comedy in subtle ways, and Best in Show stands as his greatest effort thus far. The mockumentary follows various competitors in a dog show, and explores their hopes and dreams as the competition nears. Best in Show is so sincere that it feels like a real documentary at times. Though The Chair Company is more surreal and weird, the characters in Best in Show would fit right in with Tim Robinson's band of oddballs. Guest brilliantly uses the art of film to make gags that work on so many levels, and Best in Show isn't just a funny comedy, but a well-made movie as well. The King Of Comedy (1982) Robert De Niro and Martin Scorsese did their best work together, but The King of Comedy is often overlooked. Rupert Pupkin is an aspiring stand-up comic who kidnaps a talk show host in order to get his five minutes of fame. The thrilling story puts the dark in dark comedy, and is almost too bleak to be considered strictly humorous. Like The Chair Company, The King of Comedy borrows the thriller structure and infuses it with humor. However, Scorsese's hidden gem has a lot to say about celebrity culture and what it means to be a success or failure. The movie and show are cut from the same cloth, but The King of Comedy actually has a lot to say. Friendship (2025) Tim Robinson has already built an impressive resume, and Friendship was his debut as a leading man in the movies. Robinson plays a regular suburban dad who befriends a free-spirited neighbor and becomes obsessed with impressing him. Rudd and Robinson are a match made in comedy heaven, and Friendship is just cringey enough.

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