The 1990s will always stand out as a notable transitional period in the film industry, marked by advancements in CGI and a shift from analog to digital technology. At the same time, the DVD market opened up numerous possibilities for distribution in the late 1990s, shifting interest back to home media and offering a high-quality product that could be enjoyed at home. As such, the decade is also one of the most pronounced for having surprise success stories and failures, with the box office being notably unpredictable.
When it comes to comedy, there is no shortage of films that got the short end of the stick and ended up becoming a blip during the decade, coming and going with little fanfare. Of course, the next significant advancement for the film industry, VOD and streaming, has allowed many to revisit and rediscover films from the past, championing once-maligned titles to cult status. These ten films would have flopped at the box office, but they have earned appreciation with a dedicated fandom.
10
‘The Wrong Guy’ (1997)
The Wrong Guy
- Release Date
-
August 1, 1997
- Runtime
-
92 minutes
- Director
-
David Steinberg
- Producers
-
Jon Slan
Cast
-
-
David Anthony Higgins
Det. Arlen
-
Jennifer Tilly
Lynn Holden
-
Nelson Hibbert (Dave Foley) is doing everything he can to climb the corporate ladder, going so far as to marry his boss’s daughter. Yet, when he is once again turned down, he lashes out and is seen by others stating that he wants to kill his father-in-law. So, when the boss ends up dead, with Nelson being the one to find the body, he instantly assumes he is the prime suspect. Fleeing, Nelson manages to take the same path as the real killers, and ends up becoming intertwined with police who don’t suspect him, and killers who believe he is some counter-agent.
On the Run From No One
The Canadian dark comedy was a box office failure, following the decision to skip a theatrical run and release it directly to DVD in the United States. The Wrong Guy was intended to be a launching point for actor Dave Foley to expand beyond his work with the comedy troupe Kids in the Hall, but it was dead on arrival. Still, much of the movie’s cult status remains in Canada because of David Foley being such an adored comedic figure in the country. The Wrong Guy has also captured a fan base outside of the Great White North, as it is a wonderfully absurd comedy of errors with some great set-ups for Foley to bumble his way through.
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9
‘Pecker’ (1998)
Pecker (Edward Furlong) is an 18-year-old sandwich shop worker in Baltimore whose primary life interest is photography, ranging from taking candid and unglamorous pictures of those around him to documenting his friends’ petty thefts. Yet, when a New York art dealer, Rorey Wheeler, visits the sandwich shop by happenstance and sees Pecker’s photos, he is declared a genius and is soon absorbed into the art scene, which ruins his friendships and passion for photography.
The ’90s Were Not Kind to Cult Favorite John Waters at the Box Office
The skewing of the art scene and working-class culture in an offbeat manner is John Waters to a tee, yet for mainstream audiences, it showed that the famed cult director would remain an outsider despite the movie being one of his most accessible works. Essentially, the film was just a bit too niche, but it was guaranteed cult infamy just bearing the “Pope of Trash” name. John Waters struggled to break into the mainstream, and Pecker, Serial Mom, and Cry Baby were all notable ’90s flops. Now, each is a cult classic in its own right.
8
‘Citizen Ruth’ (1996)
Ruth Stoops (Laura Dern) lives on the streets, struggling with a drug addiction that has already led to four children being taken away from her care. After a recent arrest, Ruth finds out she is pregnant again. At trial, the judge makes the unprecedented decision that Ruth could have her sentence reduced if she chooses to abort her child. This incident causes an uproar, and Ruth, who wants nothing to do with anyone or has any interest in politics, finds herself and her body in the middle of a war between pro-life and pro-choice parties.
A Brilliant Satire on a Controversial Subject That the World Was Not Ready For
Offering up one of Laura Dern’s best performances, Citizen Ruth received a limited release due to its controversial subject matter and dark satirical comedic approach. The movie would become a fan favorite and maintain a dedicated cult following, both due to Dern’s performance and director Alexander Payne’s brilliant approach to crafting a film that skewered both sides to expose the hypocrisies of both. At the same time, the movie delivers an abundance of memorable dialogue through Dern’s wicked tongue and the delusions of others who try to dictate her existence for their cause, which she gives zero f***s about; there is something quite punk-rock to her performance.
7
‘Freeway’ (1996)
Freeway
- Release Date
-
August 23, 1996
- Runtime
-
105 Minutes
- Director
-
Matthew Bright
- Writers
-
Matthew Bright
A modern and gritty take on the classic Little Red Riding Hood story, Freeway follows Vanessa Lutz (Reese Witherspoon), who leaves her drug-addicted mother and her perverted stepdad behind to start a new life. She decides to seek out her estranged grandmother as a starting point, but along the way she is abducted by a serial killer on the loose, Bob Wolverton (Kiefer Sutherland). Managing to shoot him and make an escape, Vanessa is later captured and put on trial. In prison, she plans her escape so she can exact her revenge.
Heavy Cuts and Censorship Killed ‘Freeway’
Freeway’s controversial subject matter led to multiple edits and censorship issues, and by the time it reached theaters, the soul of the film had been entirely stripped from what director Matthew Bright had anticipated. Yet, when audiences were finally able to see the movie in its full uncut glory, its satirical humor and dark themes instantly made it a cult hit.
Freeway would have a brush with pop culture, as the meme featuring Kiether Sutherland, all beaten-up and wheelchair-bound, is from the film. Despite being a flop, its subsequent infamy led to a sequel also worth checking out for those who love dark humor: Freeway II: Confessions of a Trickbaby, starring Natasha Leone in the lead.
6
‘Stay Tuned’ (1992)
Suburban couple Roy (John Ritter) and Helen Knable (Pam Dawber) are struggling in their marriage due to Roy’s obsession with TV. In a moment of frustration, Helen destroys the TV, which prompts a visit from a mysterious TV Salesman who offers them a state-of-the-art satellite with 666 channels. After installing the new system, Roy and Helen are teleported to the ‘hell dimension’ to entertain demons, but Roy’s knowledge allows him to navigate the dangerous world of satanic parodied programs.
From Flop to Nostalgic Favorite
Here is the odd thing about movies that parody the pop culture of their time: they can be painfully awkward and off the mark on release, but evoke nostalgia decades later. Upon release, Stay Tuned was met with critical scorn, back when such a response could sink a movie, and it did not even recoup half of its budget. Yet with time, people began to appreciate the film’s unique and imaginative premise, its love letter to 90s television. John Ritter and Eugene Levy’s performances here are also top-notch, and the movie utterly absorbs the viewer into the era in an utterly charming (and aptly repulsive) way, earning it cult status.
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5
‘The Vagrant’ (1992)
The Vagrant
- Release Date
-
May 15, 1992
- Runtime
-
91 minutes
- Director
-
Chris Walas
- Writers
-
Richard Jefferies
- Producers
-
Gillian Richardson
Graham Krakowski (Bill Paxton) is an uptight financial clerk who has finally saved up enough for his own home. Yet, when he notices an encampment next to his place where a deformed ‘vagrant’ lives, he becomes obsessed with the man and tries to find ways to get him removed. As Graham starts to have nightmares about the man, dead bodies start showing up. Graham becomes the police’s prime suspect, but he knows who the real killer is and tries to prove his innocence.
A Genre Mash-Up That Could Not Find Its Audience
The writing was on the wall for The Vagrant to fail at the box office. Despite incorporating elements of horror and comedy, it does not fit neatly into a specific genre, leaving its intended audience uncertain. The studios acted in kind, unsure of how to promote the film, and it received limited press and screenings. Poor critical ratings further pushed the film into obscurity.
Over time, the movie would experience a resurgence in popularity among home media and later online discourse. The unique genre mash-up makes The Vagrant a surprise standout in the 90s; it also features some phenomenal performances and highly quotable pieces of dialogue. The movie’s use of surreal storytelling elements, sharp social commentary, and impressive effects on a budget has only further cemented its legacy.
4
‘Shakes the Clown’ (1991)
Shakes the Clown
- Release Date
-
August 28, 1991
- Runtime
-
87 minutes
- Producers
-
Paul Colichman
-
-
-
Bruce Baum
Ty the Rodeo Clown
-
Steve Bean
Beaten Mime in Park
Set in the fictional town of Palukaville, Shakes the Clown follows the titular Shakes (Bobcat Goldthwait), a down-and-out alcoholic birthday entertainer. Shakes’ dreams of one day having his own show, but is living in the shadow of his arch-rival, a cocaine-addicted clown by the name of Binky (played by the voice of SpongeBob, Tom Kenny). Everything spirals though after a man is murdered at a local tavern frequented by the clowns, and Shakes’s rival clowns decide to pin it on him.
Clowning Around Did Not Pay Off at the Box Office
Niche and offbeat humor, as well as scathing reviews from critics, contributed to Shakes the Clown‘s flop at the box office. It wasn’t until much later that the movie gained appreciation, in part due to writer/director Bobcat Goldthwait’s later films finding a loving fan base (World’s Greatest Dad, Willow Creek, God Bless America). Of course, a supporting cast that included Adam Sandler and Tom Kinney also did not hurt its later cult viability. Ultimately, Shakes the Clown flopped at the box office because the world was not ready for the movie’s dark and subversive humor, which Goldthwait would later refine to great success in his career.
3
‘Rubin and Ed’ (1992)
Rubin & Ed
- Release Date
-
May 15, 1992
- Runtime
-
82 minutes
- Director
-
Trent Harris
- Producers
-
Paul Webster
Cast
-
-
Howard Hesseman
Ed Tuttle
-
-
Rubin Farr (Crispin Glover) is an eccentric recluse who lives in a motel run by his mother. With little contact with others, when his best friend, a cat, Rubin decides he needs to give it a proper burial. At the same time, his mother challenges him to go out and make at least one friend. Here, Rubin meets travelling salesman Ed Tuttle (Howard Hesseman), who is clueless about promoting a pyramid scheme. Rubin uses the man’s desire to sell to him to create a ‘friend’ who will also help him find a place to bury his cat.
“My Cat Can Eat a Whole Watermelon”
Rubin and Ed are most notable for Crispin Glover appearing on David Letterman and getting a lifetime ban in the process while appearing in character as Rubin. That little bit of infamy aside, the movie failed to drum up interest with its bizarre, offbeat humor and poor critical reception. However, with time, the film’s peculiar approach to humor won over a dedicated fan base, further bolstered by actor Crispin Glover’s emergence as a beloved outsider icon. Ultimately, Rubin and Ed is a wonderfully strange comedy that hinges on the award-winning pairing and Glover’s irreverent persona, along with a few amazing one-liners.
2
‘Dirty Work’ (1998)
Long-time friends, Mitch Weaver (Norm Macdonald) and Sam McKenna (Artie Lange), start a revenge-for-hire business to pay for their ‘pops’ medical bills. The duo’s business, “Dirty Works,” is a success, but when they cross paths with a corrupt politician, they are tricked into doing a job that ostracizes them from the community and lands them in prison. Once out, the down-and-out duo plan a way to get revenge for themselves.
From Flop to Favorite
Dirty Work was called many things upon release, but “funny” was not one of them; some even billed it as the worst comedy of all time in their reviews. Now, Dirty Work has become one of the most beloved ’90s comedies, boasting a dedicated fan base that has watched the movie numerous times. Part of this later renewed passion stems from an appreciation for Norm MacDonald’s comedic stylings, but what was initially perceived as ‘mean-spirited’ by critics in the ’90s is not quite as tame and charming by modern standards.
The movie also, in typical Norm Macdonald style, features some wonderfully absurd, drawn-out bits, with the infamous ‘Ridiculous!’ jail scene now infamous. Fans should note that the movie has just recently (May 2025) received a ‘dirtier cut’ release, which includes over seven minutes of previously cut footage to make it more theatrical-friendly at the time, including more on the aforementioned jail scene.
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1
‘The Frighteners’ (1996)
Frank Bannister (Michael J. Fox), once a prominent architect, now lives a life among the dead after a car accident took the life of his wife and granted him the ability to see ghosts. He uses this ability to scrape by running a business where he gets rid of ghosts for people, using his friends from the cemetery where he lives to wreak havoc on his targets. When a Grim Reaper-like entity appears in town and starts killing people, as well as other ghosts, Frank finds himself having to solve a deadly mystery to save the few left he cares about.
Peter Jackson’s Early Box Office Bomb
Given an R-rating and being released within the same timeframe as Independence Day and during the Olympics, The Frighteners did not stand a chance at the box office. Perhaps more important when considering its failure, at the time of the movie’s release, director Peter Jackson had a cult following and was yet to become a big-name draw. Of course, as Jackson became revered, many would revisit the film and see it for what it truly is: a charming horror comedy.
