The comedy movies of the 1990s include some of the most iconic additions to the genre and some of the most bizarre. Experimentation and exploration were a large part of filmmaking in the '90s, and while this can be exciting, it also can be off-putting for audiences who watched these projects. The tone, visuals, and scattered storytelling styles of these films all contributed to their reputations as unusual and confusing works that lost their sense of humor. However, even though they're considered more weird than hilarious, many of them have become cult classics.

There are also plenty of 2000s comedy movies that were strange, as every decade features films that take big risks and test out new forms of comedy. It's interesting to look back at these projects since so many feature big stars. Though not every movie that's considered out there is a critical and box office failure, many of these projects were panned and ended up making little to no money in theaters. While this isn't the only way to measure the quality of a movie, it does show that viewers didn't immediately connect with the uncanny tone of these films.

8 Shakes The Clown (1991)

Directed by Bobcat Goldthwait

It's fair to say that Shakes the Clown is not a movie from the 1990s that's considered a masterpiece. Despite this, the high concept of Shakes the Clown and its exploration of the tropes and stereotypes that surround both clown performers and the comedy scene in general make it an interesting, if strange, watch. The film follows Shakes (Bobcat Goldthwait) as he navigates the clowning community, which is rife with corruption, substance abuse, and eventually murder.

The juxtaposition between the humor and silliness of clowning and the darkness of the story comes to the forefront of Shakes the Clown, almost transforming the movie into a drama by the end.

The juxtaposition between the humor and silliness of clowning and the darkness of the story comes to the forefront of Shakes the Clown, almost transforming the movie into a drama by the end. Despite the comedic tone, Shakes the Clown takes a serious look at its heavy subject matter, but this tonal shift can be jarring for viewers who were expecting a different kind of clown movie. Shakes is a troubled protagonist who goes through a lot in Shakes the Clown​​​​​​, and the audience will feel for him even as the narrative spirals into chaos.

7 Drop Dead Fred (1991)

Directed by Ate de Jong

Audiences familiar with Drop Dead Fred might feel nostalgic for the offbeat comedy, as it's all about how imaginary friends are a vital escape for children. However, in Drop Dead Fred, Elizabeth's (Phoebe Cates) imaginary friend, the titular Fred (Rik Mayall), comes back with a vengeance in adulthood. Through lots of mayhem and hijinks, Fred slowly helps Elizabeth work through the problems in her life and assert her independence. While this is a nice premise, the surreal visual style and haphazard story make it difficult to follow Drop Dead Fred​​​​​​.

Elizabeth and Fred take center stage, but the ing cast helps anchor the story in some sort of reality. Though her work in Drop Dead Fred isn't ed as one of Carrie Fisher's best roles outside of Star Wars, she's hilarious and a breath of fresh air throughout the project, as always. Looking at Drop Dead Fred through the lens of magical realism and childhood trauma allows the viewer to understand the story, but it doesn't make it less bizarre.

6 Coneheads (1993)

Directed by Steve Barron

Despite the success of the "Conehead" sketches on SNL, transforming these short skits into a feature-length movie didn't work out well. The 1993 Coneheads movie has some fun jokes and throw-away moments that are reminiscent of the iconic sketch show, but part of the reason the Coneheads worked in this short form is that there's really only one essential joke to make about aliens living on Earth. Revisiting Coneheads today is even stranger, as audiences aren't familiar with the sketch and don't know the premise of Coneheads​​​​​​.

It's too bad that Coneheads couldn't naturally expand its premise, as Dan Aykroyd, Jane Curtin, and Michelle Burke all work hard to make the audience care about the story.

It's too bad that Coneheads couldn't naturally expand its premise, as Dan Aykroyd, Jane Curtin, and Michelle Burke all work hard to make the audience care about the story. While there are plenty of sci-fi films that blend comedy into their plots, and it isn't uncommon to see aliens coming to Earth in the movies, there's something off about Coneheads. Though Coneheads does make some commentary about the experience of being an immigrant in America, the story is too goofy to tackle this subject with grace.

5 Theodore Rex (1995)

Directed by Jonathan R. Betuel

Theodore Rex is a comedic fantasy movie that goes off the rails and is not an addition to Whoopi Goldberg's filmography that fans of the actress are likely to . Blending the cop genre, sci-fi, and elements of fantasy, Theodore Rex covers a lot of ground, but the premise might make audiences wonder how the project got made. While Goldberg was a big enough name in the '90s to appeal to audiences, Theodore Rex doesn't make good use of her talents, making her play off a giant Tyrannosaurus puppet.

Universally panned by critics and audiences, Theodore Rex uses a formula of pairing a seasoned cop, Kaite (Goldberg), with a partner they don't initially get along with, the dinosaur, Theodore Rex. However, even though this structure is tried and true, there's little way that pairing a dinosaur with a human can work. The use of puppetry is visually interesting, and the design of Theodore isn't terrible, but this isn't enough to save Theodore Rex​​​​​​.

4 Freaked (1993)

Directed by Alex Winter & Tom Stern

Alex Winter, best known for his work in the Bill & Ted franchise, partnered with Tom Stern to make the grotesque comedy Freaked in the early '90s. Winter stars as Ricky, the film's protagonist who goes on a nightmarish adventure that will keep audiences up at night for weeks after watching Freaked. An over-the-top allegory about the dangers of chemical experimentation, environmental protection, and the mistreatment of people who are different, Freaked is too unusual to let its points hit home.

The conspiracy at the heart of Freaked grows larger with every ing moment, and the plight of the characters comes off as too dark and dangerous to be funny.

Most of the story revolves around a dangerous compound that turns people into "freaks," which is visually represented with vivid prosthetics and practical effects that can be hard to watch. The conspiracy at the heart of Freaked grows larger with every ing moment, and the plight of the characters comes off as too dark and dangerous to be funny. Though it's interesting to look back on the movie, it's an off-putting project that will shock audiences.

3 Ed (1996)

Directed by Bill Couturié

A few years after being catapulted to fame for his role as Joey in Friends, Matt LeBlanc tried to break out into the film sphere with his offbeat twist on the buddy comedy Ed. LeBlanc plays opposite a chimpanzee in Ed, and while there have been instances when human-animal collaborations have worked onscreen, Ed was not one of them. Set against the backdrop of a minor league baseball team, Ed sees Jack "Deuce" (LeBlanc) the team and strike up a friendship with the mascot, Ed.

It's almost uncanny how many issues and hijinxs Ed gets into throughout the film's runtime and how quickly Deuce accepts that his new roommate is a chimp. Though LeBlanc still lends his charisma to the story, this doesn't make up for the fact that Ed just doesn't make sense. It relies on cheap laughs to keep the audience interested. Ed lacks a clear vision and takes itself too seriously for the audience to believe that the film is in on the joke of how bizarre the premise is.

2 Mystery Men (1999)

Directed by Kinka Usher

As time has progressed, Mystery Men has come to be known as a cult classic thanks to the work of the star-studded ensemble cast. Ben Stiller leads Mystery Men as Roy, one of the superheroes who attempt to save the day and achieve fame in the film. Roy and his ragtag team of slightly lesser superheroes with more unassuming powers fuel the humor of Mystery Men, as many of the invented powers are funny but very unusual.

While the plot of Mystery Men isn't the strongest, the charm of the lead actors helps propel the story, even when it starts to get out of control. Mystery Men pokes fun at the tropes and pitfalls of the superhero genre and examines a world where more normal people have powers and don't always know what to do with them. However, this sometimes creates confusion, as Mystery Men will overdo the individual jokes and lose sight of the overarching cohesion of the narrative.

1 Serial Mom (1994)

Directed by John Waters

Out of every John Waters movie, Serial Mom is one of the director's projects that has the most mainstream appeal. It stars Kathleen Turner as Beverly and Sam Waterston of Law & Order as her husband, Eugene. The dark comedy film gets increasingly violent and over-the-top as the story progresses. Waters is well-known for his use of satire to critique the concept of the American Dream and the nuclear family, which he does by making Beverly a mild-mannered housewife who's secretly a bloodthirsty serial killer.

Beverly doesn't look like the typical serial killer viewers associate with these roles. However, she handles the work effectively and outwits everyone who tries to bring her down at every turn. While the juxtaposition between Beverly's archetypal role and her actions is funny, Serial Mom gets extremely violent and includes plenty of unexpected plot twists. Ending in a trial scene that upends audience expectations of the narrative, Serial Mom is a movie that has to be seen to be believed.