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 of2000s 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.

It’s fair to say thatShakes the Clownis not amovie from the 1990s that’s considered a masterpiece. Despite this, the high concept ofShakes the Clownand 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 navigatesthe 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 ofShakes 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 ofShakes the Clown, almost transforming the movie into a drama by the end. Despite the comedic tone,Shakes the Clowntakes 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 inShakes the Clown, and the audience will feel for him even as the narrative spirals into chaos.
Shakes the Clown (1991)

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Audiences familiar withDrop Dead Fredmight feel nostalgic for the offbeat comedy, as it’s all about how imaginary friends are a vital escape for children. However, inDrop 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 followDrop Dead Fred.
Elizabeth and Fred take center stage, butthe supporting cast helps anchor the story in some sort of reality.Though her work inDrop Dead Fredisn’t remembered as one ofCarrie Fisher’s best roles outside ofStar Wars, she’s hilarious and a breath of fresh air throughout the project, as always. Looking atDrop Dead Fredthrough the lens of magical realism and childhood trauma allows the viewer to understand the story, but it doesn’t make it less bizarre.

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Despite the success of the “Conehead” sketches onSNL, transforming these short skits into a feature-length movie didn’t work out well. The 1993Coneheadsmovie has some fun jokes and throw-away moments that are reminiscent of the iconic sketch show, but part of the reason theConeheadsworked in this short form is that there’s really only one essential joke to make about aliens living on Earth.RevisitingConeheadstoday is even stranger,as audiences aren’t familiar with the sketch and don’t know the premise ofConeheads.
It’s too bad thatConeheadscouldn’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 thatConeheadscouldn’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 aboutConeheads. ThoughConeheadsdoes make some commentary about the experience of being an immigrant in America, the story is too goofy to tackle this subject with grace.
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Theodore Rexis a comedicfantasy movie that goes off the railsand isnot an addition to Whoopi Goldberg’s filmography that fans of the actress are likely to remember.Blending the cop genre, sci-fi, and elements of fantasy,Theodore Rexcovers 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 Rexdoesn’t make good use of her talents, making her play off a giant Tyrannosaurus puppet.
Universally panned by critics and audiences,Theodore Rexuses 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 saveTheodore Rex.
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Alex Winter, best known for his work in theBill & Tedfranchise, partnered with Tom Stern to make the grotesque comedyFreakedin 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 watchingFreaked.An over-the-top allegory about the dangers of chemical experimentation,environmental protection, and the mistreatment of people who are different,Freakedis too unusual to let its points hit home.
The conspiracy at the heart ofFreakedgrows larger with every passing 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 ofFreakedgrows larger with every passing 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.
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A few years after being catapulted to fame for his role as Joey inFriends, Matt LeBlanc tried to break out into the film sphere with his offbeat twist on the buddy comedyEd. LeBlanc plays opposite a chimpanzee inEd, and while there have been instances when human-animal collaborations have worked onscreen,Edwas not one of them. Set against the backdrop of a minor league baseball team,Edsees Jack “Deuce” (LeBlanc) join 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 thatEdjust doesn’t make sense. It relies on cheap laughs to keep the audience interested.Edlacks a clear vision andtakes itself too seriously for the audience to believe that the film is in on the jokeof how bizarre the premise is.
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As time has progressed,Mystery Menhas come to be known as a cult classicthanks to the work of the star-studded ensemble cast. Ben Stiller leadsMystery Menas 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 ofMystery Men, as many of the invented powers are funny but very unusual.
While the plot ofMystery Menisn’t the strongest, the charm of the lead actors helps propel the story, even when it starts to get out of control.Mystery Menpokes fun at the tropes and pitfalls of the superhero genreand examines a world where more normal people have powers and don’t always know what to do with them. However, this sometimes creates confusion, asMystery Menwill overdo the individual jokes and lose sight of the overarching cohesion of the narrative.
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Out ofevery John Waters movie,Serial Momis one of the director’s projects that has the most mainstream appeal. It stars Kathleen Turner as Beverly and Sam Waterston ofLaw & Orderas 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 killerviewers 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 Momgets extremely violent and includes plenty of unexpected plot twists. Ending in a trial scene that upends audience expectations of the narrative,Serial Momis a movie that has to be seen to be believed.
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