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

HBO’s The Chair Company is a brilliantly funny and awkward comedy series, and it’s sure to leave you wanting more laughs. Created by Tim Robinson, the show is a standout for its unique and offbeat humor. The Chair Company takes Robinson’s signature absurd style and expands on it, making it one of the most original comedies in recent years.

The show excels at taking everyday scenarios and escalating them to absurd levels, creating a wonderfully awkward and suspenseful atmosphere. While Tim Robinson has mastered this comedic style in shows like I Think You Should Leave, the continuous storyline of The Chair Company is what truly sets it apart.

Many movies share a similar vibe to HBO’s new series. Though the stories are different, several films offer the same kind of funny, awkward, and lighthearted moments that will leave you chuckling long after you finish watching The Chair Company.

Drop Dead Gorgeous (1999)

Even though it didn’t receive great reviews, Drop Dead Gorgeous is considered one of the funniest movies from the 1990s. This mockumentary follows the quirky contestants in a local beauty pageant and how far they’ll go to win. Featuring rising stars like Kirsten Dunst and Brittany Murphy, the film really captures the spirit of the time.

Despite being very different in style, Drop Dead Gorgeous and The Chair Company both have that same awkward, heartfelt honesty. They both use elements of thriller movies, but deliver the suspense with uncomfortable humor. Drop Dead Gorgeous was a clear inspiration for many comedies that followed.

After Hours (1985)

As a big movie fan, I always associate Martin Scorsese with his intense dramas, but he’s surprisingly funny too! One of my favorites is After Hours. It’s about this really stressed-out guy who just wants to escape work, and ends up having the most unbelievably wild night in New York City. It’s a really unique comedy – it’s both hilariously over-the-top and makes you squirm with embarrassment, and it totally stands out as one of the best comedies of the 80s.

I absolutely love how After Hours takes these totally normal, everyday situations and cranks up the absurdity to eleven – it’s just laugh-out-loud funny, kind of like The Chair Company. What really gets me is how Scorsese builds the tension; each scene feels like it’s escalating into something even crazier, and he’s a master at making you feel totally uneasy while you’re watching. It’s a really fast-paced movie, but it’s not just thrilling, it’s genuinely hilarious too.

Brian And Charles (2022)

The quirky comedy Brian and Charles, directed by Jim Archer, didn’t get much attention when it came out, but it’s definitely worth watching. The film tells the story of a solitary man in Wales who builds a robot friend, and how that robot helps him connect with the world. Rather than relying on awkward humor, Brian and Charles is funny because it’s genuinely sweet and silly.

If you enjoyed The Chair Company, you’ll likely love Brian and Charles. While the humor is different, both share a playful and inventive approach to comedy. This 2022 film is both funny and genuinely heartwarming.

Shiva Baby (2020)

Rachel Sennott delivered an Oscar-worthy comedic performance in Shiva Baby, a film that deserves wider recognition. The movie centers on a young woman who unexpectedly encounters people from different parts of her life while attending a funeral, leading to a series of uncomfortable and funny moments. Emma Seligman’s comedy is hilariously awkward and subtly brilliant.

Like the low-budget, character-driven films of the 2000s, Shiva Baby leans into uncomfortable moments and makes them work. While more subdued than The Chair Company, it’s equally awkward and surprisingly insightful, offering a relatable look at the challenges of being a young adult.

The 40-Year-Old Virgin (2005)

Considered a defining comedy of the 2000s, The 40-Year-Old Virgin is still a hugely popular film. It follows a man who, at age 40, has never been in a relationship and is suddenly pushed into the world of dating. Steve Carell delivers an unforgettable performance as a sympathetic and endearing character in a truly awkward situation.

Okay, so The Chair Company is kind of the flip side of The 40-Year-Old Virgin. In that movie, the guy’s the weird one, but here, it’s… well, it creates a similar vibe. Honestly, The Chair Company has its share of awkward scenes, but it still feels like a classic early 2000s comedy – it’s got that polished look and easygoing energy. But for me, The 40-Year-Old Virgin just nails it – it’s funny and relatable, the perfect mix.

Lost In America (1985)

Albert Brooks made several fantastic comedies that didn’t get enough attention, and Lost in America is arguably his masterpiece. The film follows a young, professional couple who sell everything to travel the country, but their trip quickly becomes a series of unfortunate events. This ’80s favorite cleverly satirizes the trends and values of that decade, as well as the Baby Boomer generation as a whole.

I have to say, what really makes Lost in America work is how much you connect with the main characters. It’s precisely because they feel so real that it’s so funny when things start to fall apart for them. A lot of the humor comes from watching them make genuinely well-intentioned, but terrible choices – it reminded me a bit of the vibe in The Chair Company. But where that film was broader, Brooks delivers his comedy with a much drier, more subtle touch. It’s a really clever approach.

Death At A Funeral (2007)

Frank Oz’s Death at a Funeral didn’t get much attention when it first came out in 2007, but it’s now considered a hilarious and beloved comedy. The movie follows a quirky family brought together by a death, and chaos quickly ensues. It’s a fast-paced comedy that never lets up.

As a comedy fan, I was completely hooked! This movie is a total whirlwind of hilarious accidents and awkward situations – you can’t help but squirm in your seat! Honestly, compared to something like The Chair Company, it’s just so much bolder and over-the-top. It doesn’t try to be profound or make a big statement, and you know what? That’s perfectly fine. It’s pure, unadulterated fun, and the laughs are what really count.

Best In Show (2000)

Christopher Guest is known for his funny and awkward comedies, and Best in Show is widely considered his best film. This mockumentary playfully follows people competing in a dog show, highlighting their ambitions and what motivates them. It’s so realistically made that it often feels like a genuine documentary.

While The Chair Company leans into the surreal, the characters from Best in Show feel like they’d easily fit into the world created by Tim Robinson and his eccentric characters. Director Christopher Guest is a master of filmmaking, crafting jokes that are clever and layered, and Best in Show is not only hilarious but also a genuinely well-made film.

The King Of Comedy (1982)

Robert De Niro and Martin Scorsese created some of their most memorable films together, but The King of Comedy doesn’t always get the attention it deserves. The film follows Rupert Pupkin, a struggling comedian who resorts to kidnapping a talk show host in a desperate attempt to become famous. It’s a gripping story that leans heavily into dark humor, and is so unsettling it’s hard to consider it purely funny.

Similar to The Chair Company, The King of Comedy uses the framework of a thriller but adds comedic elements. However, Scorsese’s film is more than just funny – it offers a sharp commentary on celebrity culture and what defines success and failure. While both works share similarities, The King of Comedy ultimately delivers a more meaningful message.

Friendship (2025)

Tim Robinson is already known for his great work, and Friendship marks his first starring role in a film. He plays an average dad who becomes determined to win over a new, outgoing neighbor. Paul Rudd and Tim Robinson have fantastic chemistry, and Friendship strikes the perfect balance between funny and awkward.

Like Tim Robinson’s earlier web series, The Chair Company, his new show Friendship is full of uncomfortable and bizarre humor. Given Robinson’s distinct comedic style, it’s fitting that his first leading role would result in something so similar to his well-known online work.

2025-11-09 21:41