While the 1990s had a fair share of average rom-coms that were comfort films for many viewers, there’s a huge catalog of comedies from the era that were anything but average in terms of story, reception by audiences and critics, and resulting legacy. Properly categorized as cult comedies, some of them were released under clunky studio conditions, and others just didn’t have enough backup from distribution companies. They deserved more exposure because they were the black sheep that were often funnier than their formulaic peers.
Yet this doesn’t make all of them classics. Only a few survived from years of revisits and reconsiderations, and today, they’re seen as more than just nostalgic products of one of cinema’s most peculiar decades. We took a trip down the turn of the century and made a list of the best cult classic comedies from the 1990s that are available to stream today (some for free).
10 Flawless (1999)
Available to Stream on Tubi
Flawless is the story of Walter Koontz, a retired security guard who lives in an apartment building where he doesn’t get along with anyone, especially with Rusty, a drag queen who lives next door. When Walter suffers a stroke trying to protect the building, he’s paralyzed and loses his ability to speak properly. The grumpy and foul-mouthed man is forced to hire Rusty to give him singing lessons for a quicker recovery.
Written and directed by Joel Schumacher, Flawless is one of the few “sober” films he ever did. It stars Robert De Niro and Philip Seymour Hoffman in two powerhouse performances, and their presence probably made for half the production budget. This box office bomb is very underrated and very funny; it carries a lot of heart in its formula-based turning of character for the conservative Walter.
9 Office Space (1999)
Available to Stream on Hulu
- Release Date
- February 19, 1999
Office Space follows Peter, a frustrated programmer working for a software company who’s very unhappy with his job. His relationship with his girlfriend is a bit rusty, and his co-workers don’t make it easy for him. Every day is an ordeal for Peter, until one day he decides to fight back against everything that’s wrong with the office system.
Mike Judge’s memorable satire of the office world is a film that doesn’t feel dated at all. However, back in 1999, it wasn’t very popular (even with the presence of Friends‘ Jennifer Aniston), and it wasn’t until it was released on home video that it got the cult following it deserved. Today, it’s regarded as one of the finest and smartest comedies ever made.
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8 Galaxy Quest (1999)
Available to Stream on PlutoTV
- Release Date
- December 23, 1999
In Galaxy Quest, the cast of the Star Trek-esque show Galaxy Quest constantly meet at conventions. Jason, the faded lead of the show, one day meets a group of fans who take Galaxy Quest too seriously. When they prove they are real aliens, Jason decides to gather the rest of the cast to convince him they now have a real mission in a galaxy far, far away.
Galaxy Quest is an extremely funny comedy that plays as a spoof on the entertainment industry, toxic fandom, and sci-fi in general. It stars a great ensemble cast that includes Sigourney Weaver, Alan Rickman, Tim Allen, Sam Rockwell, Daryl Mitchell, and Tony Shalhoub. It had a modest box office performance, but throughout the years, it earned cult status that made it a memorable film for sci-fi fans who didn’t have a problem laughing about themselves.
7 Clerks (1994)
Available to Stream on PlutoTV
- Release Date
- September 13, 1994
Clerks is the story of the very unhappy Dante Hicks, an employee working in a convenience store who constantly gets harassed by unsatisfied clients, but also by his boss who keeps assigning him shifts. Dante and his friend Randal, who works at the video rental store next door, face the hardships of young age while having to stay trapped in very disheartening jobs.
Kevin Smith’s small experiment made for less than $30,000 is a beautiful piece of independent cinema. Clerks is Smith’s debut, and a very solid introduction to a world he would revisit many times because it seemed to click from a generational standpoint. The original ending was very bleak and bold when compared to the comedic elements of the film, so it was changed, and it paved the way for an entire franchise.
6 The Big Lebowski (1998)
Available to Stream on Prime Video
The Big Lebowski
In The Big Lebowski, Jeffrey Lebowski has the same name as a very powerful man. “The Dude,” as he calls himself, is mistaken for the other guy with the name and beaten by thugs. When the wife of the rich Jeff Lebowski gets kidnapped, The Dude jumps on board to deliver ransom money and earn some cash, but his very peculiar friends have another plan.
This box office flop by Joel and Ethan Coen is a strange case of a movie with a great cast and a funny story which wasn’t very well-received upon release. As time passed, audiences and critics revisited it, and eventually, it became the classic it is today. A current score of 80% on Rotten Tomatoes is no match for the cultural impact The Big Lebowski has had in recent years, with many considering it the Coens’ funniest and most bizarre film.
5 The Cable Guy (1996)
Available to Stream on Hulu
The Cable Guy follows Steven, a successful man having to move to an apartment alone because his marriage proposal didn’t have a good result. Steven gets cable service and the installer, Chip Douglas, is a bit too… nosy. However, he insists it’s all out of love and friendship. When Chip really gets into Steven’s life, he realizes his cable deal came with more than he bargained for.
Directed by Ben Stiller, The Cable Guy is a great example of dark comedy in the hands of a comedian who always seemed to be out of control in all his movies. But Jim Carrey gives one of his best restrained performances, albeit with his trademark physicality. Although it wasn’t a very successful film with critics, the very eerie comedy obtained a well-earned cult status from audiences who revisit it constantly.
4 Singles (1992)
Available to Stream on Tubi
- Release Date
- September 18, 1992
In Singles, a group of young people from a Seattle suburb try to survive the tribulations that their lives throw at them. Janet, Steve, Linda, Cliff, and Debbie go through several stages of all kinds of relationships, and the apartment block where they hang out seems to be the center of the universe for these transitioning, but sometimes immature, adults. This is how grunge was born.
Cameron Crowe’s depiction of the music scene in early ’90s Seattle is a beautiful and relaxed blend of romance and comedy, all seen through well-designed characters. They’re reflections of a broader sentiment that was very particular and even served as the backdrop for an entire genre of music. The film had a good reception back then, but most remember it solely because it features cameos by members from bands like Pearl Jam, Soundgarden, and Alice in Chains.
3 Clueless (1995)
Available to Stream on Prime Video
Cher is a typical teenager living in Beverly Hills in the 1990s. Her friends share her posh lifestyle, but when a new transfer student arrives at her high school, Cher doesn’t get all the attention she’s used to. This sends her into a spiral that’ll make her change her priorities and see things in an entirely different way.
Amy Heckerling adapts a Jane Austen classic remodeled for modern times and achieves an entertaining film starring Alicia Silverstone during her Hollywood arrival. While its legacy wasn’t visible until years later, Clueless is a classic coming-of-age movie with enough shallowness and materialism to represent a great balance that makes it a not-so-serious film.
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2 Romy and Michele’s High School Reunion (1997)
Available to Stream on Hulu
- Release Date
- April 25, 1997
Romy and Michele’s High School Reunion is the story of two young women living together in California who have been friends since high school but who are not very successful today. Romy works at a car dealership, but Michele is unemployed. When they find out about a 10-year high school reunion, Romy and Michele get the opportunity to turn their lives around, at least in the eyes of their former classmates.
The film wasn’t very successful back in the day, but after a home video release and TV airings, it got a cult status that’s alive to this day (there were even talks of a sequel at one point). It’s undoubtedly a showcase for Lisa Kudrow and Mira Sorvino, who play the lead characters and who managed to make an impact with a relatively obscure comedy.
1 Four Rooms (1995)
Available to Stream on Hoopla or Kanopy
- Release Date
- December 9, 1995
Four Rooms is an anthology composition of many genres. Nevertheless, comedy is at the center of it: Ted, a bellhop at the Hotel Mon Signor, becomes the witness to very strange guests and their bizarre stories that range from the darkly hilarious to the supernatural.
Featuring segments by Quentin Tarantino and Robert Rodriguez during their prime and performances by Tim Roth, Madonna, Antonio Banderas, Marisa Tomei, and Jennifer Beals, you would have thought Four Rooms would have more success. But the film was a box office bomb and critically panned. Nevertheless, in retrospect, it’s a very interesting exercise of screwball comedy tropes mixed with horror.