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25 Offbeat Comedies That Still Holds Up To This Day

While comedy films can become instant classics and box office blockbusters, there are always outliers that were too strange or gloomy for their time’s audiences.

Most comedy films age like milk due to changing sensibilities and outdated cultural references. But in some rare instances, a comedy film, no matter how strange can controversial, may be able to find a new wave of critical acclaim, as well as a loyal cult fanbase.

As a result, I’ve compiled a list of 25 remarkable (and unusual) comedies that have endured the test of time and are worth seeing right away! These amusing films have the potential to distort your mind if they don’t first break your funny bone.

#1 Idiocracy

Source: 20th Century Fox / Courtesy Everett Collection

First off is Mike Judge’s unmistakably hilarious satire of the future of American culture. It may have been misinterpreted by its studio during its initial release, but it has since become a stone-cold cult classic that gets more prescient as time passes.

#2 Black Dynamite

Source: Apparition / Courtesy Everett Collection

A wickedly amusing parody of a blaxploitation action picture. Michael Jai White packs a powerful comedy punch as he follows a Kung fu-savvy vigilante who encounters drug traffickers, ninjas, and a vast government conspiracy while defending his community.

#3 Serial Mom

Source: Universal Pictures / Courtesy Everett Collection

John Waters’ spectacular and gruesome comedy is about a housewife and mother who chooses to keep up with the Joneses by murdering everyone who threatens her happy household. Kathleen Turner is an absolute delight.

#4 Four Lions

Source: Film4 Productions / Courtesy Everett Collection

In this button-pushing satire comedy about inept suicide bombers, British shock master Chris Morris had spectators gasping in between spurts of screaming laughter. It features stunning early performances from The Night Of’s Riz Ahmed and What We Do in the Shadows’ Kayvan Novak.

#5 Rubin & Ed

Source: IRS Releasing / Courtesy Everett Collection

Trent Harris’ weird and zany buddy comedy is about two misfits who travel into the desert to bury a frozen cat. Crispin Glover, and Howard Hesseman make an incredibly entertaining match.

#6 Kingpin

Source: MGM / Courtesy Everett Collection

Following the massive success of Dumb and Dumber, the Farrelly brothers delivered another comedic tour de force about a crippled former bowler (Woody Harrelson) who decides to mentor an Amish bowling prodigy (Randy Quaid). The pair is brought into conflict with the sleazy yet esteemed bowler (Bill Murray) responsible for the former’s accident.

#7 Romy and Michele’s High School Reunion

Source: Buena Vista Pictures / Courtesy Everett Collection

David Mirkin’s brilliantly unconventional comedy follows a couple of snooty underachievers. Starring Mira Sorvino and Lisa Kudrow, the pair plan to transform their lives by telling a big lie at their high school reunion.

#8 Freddy Got Fingered

Source: 20th Century Fox / Courtesy Everett Collection

The title should tell you if Tom Green’s transgressive feature film debut is for you. If you enjoy jaw-dropping shock humor grounded by real good-natured optimism about life and family values, you might be the perfect audience for this cult masterpiece.

#9 Welcome to the Dollhouse

Source: Suburban Pictures / Entertainment Pictures / Alamy

Todd Solondz made an impression on the independent film scene with this incisive coming-of-age comedy. It’s about a seventh-grade girl trying to find her place in the world among her dysfunctional family, demeaning classmates, and bothersome objects of her devotion.

#10 The Ten

Source: Think Film / Courtesy Everett Collection

David Wain’s sophomore movie, Wet Hot American Summer, is a star-studded comedic anthology with ten interconnected episodes, each of which revolves around one of the Ten Commandments.

#11 Dirty Work

Source: Universal / Courtesy Everett Collection

The late, great Bob Saget and Norm Macdonald collaborated on this unforgettable twisted film about two brothers who launch a vengeance-for-hire business to pay for their father’s emergency heart surgery.

#12 Hot Rod

Source: Paramount / Courtesy Everett Collection

The Lonely Island’s underappreciated debut picture is a side-splitting display of nonstop laughter. It showcases the emerging comedic abilities of costars Bill Hader and Danny McBride, as well as a scene-stealing Ian McShane.

#13 Jawbreaker

Source: Tristar Pictures / Courtesy Everett Collection

Rose McGowan, Judy Greer, Rebecca Gayheart, Julie Benz, and Pam Grier are all excellent in Darren Stein’s insane dark comedy. The plot revolves around a clique of adolescent socialites attempting to cover up an unintentional murder caused by a prank gone bad.

#14 Shakes the Clown

Source: IRS Media / Courtesy Everett Collection

A habitually drunk party clown must clear his name after being framed for the death of his boss by a group of felonious competitors. The film was a passion project for director and performer Bobcat Goldthwait.

#15 Tucker & Dale vs. Evil

Source: Maple Pictures / Courtesy Everett Collection

In Eli Craig’s spot-on slasher movie parody, Alan Tudyk and Tyler Labine dazzle as two well-meaning backwoods boys who are mistakenly branded as bloodthirsty rednecks after rescuing an injured young woman.

#16 Used Cars

Source: Columbia Pictures / Courtesy Everett Collection

Kurt Russell is the front-runner. The great 1980 ensemble comedy by Robert Zemeckis is about competing used car dealerships. They fall to new lows to destroy and embarrass one another through underhanded promotional practices.

#17 Grosse Pointe Blank

Source: Buena Vista Pictures / Courtesy Everett Collection

George Armitage’s deliciously wicked romantic comedy. It’s about an unfocused professional assassin (John Cusack) accepts a job near his 10-year high school reunion. He soon rediscovers an old flame (Minnie Driver) while fretting about a slew of new foes.

#18 Cannibal! The Musical

Source: Troma Entertainment / Prod.DB / EAvenging Conscience / Alamy

The debut feature film from South Park founders Matt Stone and Trey Parker is a wildly strange musical. It’s a retelling of Alferd Packer’s tragic and brutal real story of desperation and death in the Colorado mountains.

#19 Best in Show

Source: Warner Bros / Courtesy Everett Collection

In this satirical mockumentary made by Christopher Guest, numerous bizarre people compete in the famous Mayflower Dog Show. It has earned a cult audience across decades.

#20 Drop Dead Gorgeous

Source: New Line Cinema / Courtesy Everett Collection

This macabre mockumentary follows a small-town beauty pageant in which the candidates begin to die in increasingly strange circumstances. It stars Ellen Barkin, Allison Janney, Denise Richards, Kirsten Dunst, and Brittany Murphy It’s directed by The State’s Michael Patrick Jann.

#21 Eagle vs. Shark

Source: Miramax / Courtesy Everett Collection

Taika Waititi’s directorial debut is a dry and bizarre romantic comedy. It revolves around a miserable gamer and an aspiring musician who foster a growing romance despite their increasingly ludicrous existence.

#22 Kids in the Hall: Brain Candy

Source: Paramount / Courtesy Everett Collection

The Kids in the Hall made their first (and only) big-screen appearance with this film about a pharmaceutical business that develops a revolutionary anti-depressant with a frightening side effect.

#23 Young Adult

Source: Paramount Pictures / Courtesy Everett Collection

Diablo Cody and Jason Reitman reunited for this cringe masterpiece about an alcoholic YA writer who tries to court her old high school flame at his newborn daughter’s party.

#24 Freaked

Source: 20th Century Fox Film Corp / Courtesy Everett Collection

This provocative, over-the-top film stars Alex Winter as a self-centered celebrity publicist who goes on a publicity stunt. It soon lands him in the clutches of a mad scientist hell-bent on adding him to his zoo of monstrosities.

#25 Harold and Maude

Source: Paramount Pictures / Courtesy Everett Collection

Hal Ashby’s cult classic from 1971 depicts a death-obsessed 20-year-old who finds a new lease on life when he falls in love with an eccentric 80-year-old widow.

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