Ken W. Hanley 
25 Demented Cult Comedies That Hold Up To This Day
While comedy movies can become instant classics and box office sensations, there are always the outliers that were too weird or dark for the audiences of their time.
Ironically, while time is often detrimental to comedies due to changing sensibilities and outdated cultural references, these absurd and controversial comedies will often find appreciation and a loyal cult audience in the years that follow. As such, I’ve put together a list of 25 exceptional (and strange) comedies that have stood the test of time and are worthy of checking out ASAP!
1. Harold and Maude
Paramount Pictures / Courtesy Everett CollectionJuno collaborators Diablo Cody and Jason Reitman reunited for this cringe masterpiece about an alcoholic YA writer who attempts to woo her old high school flame at a party for his newborn daughter.
Where to Watch: HBO Max
If you like this, you might also enjoy: Jody Hill’s Observe and Report
4. Kids in the Hall: Brain Candy
Paramount / Courtesy Everett CollectionSketch comedy legends The Kids in the Hall made their first (and to date, only) impression on the big screen with this flick about a pharmaceutical company that creates an innovative anti-depressant that carries a shocking side-effect.
Where to Watch: Xfinity Stream
If you like this, you might also enjoy: John Patrick Shanley’s Joe Versus the Volcano
5. Eagle vs. Shark
Miramax / Courtesy Everett CollectionThe directorial debut of Taika Waititi, this dry and strange romantic comedy surrounds a depressed gamer and an aspiring musician who foster a blossoming romance during their increasingly ridiculous existence.
Where to Watch: Video-on-Demand
If you like this, you might also enjoy: Colin Trevorrow’s Safety Not Guaranteed
6. Drop Dead Gorgeous
New Line Cinema / Courtesy Everett CollectionDirected by The State‘s Michael Patrick Jann, this dark mockumentary starring Ellen Barkin, Allison Janney, Denise Richards, Kirsten Dunst, and Brittany Murphy follows a small town beauty competition in which the contestants begin to die in increasingly suspicious circumstances.
Where to Watch: DVD/Blu-ray
If you like this, you might also enjoy: Robert Zemeckis’ Death Becomes Her
7. Best in Show
Warner Bros / Courtesy Everett CollectionChristopher Guest’s satirical mockumentary about the myriad absurd personalities participating in the esteemed Mayflower Dog Show garnered a vocal audience across a number of generations after becoming an unwavering staple of cable television.
Where to Watch: HBO Max
If you like this, you might also enjoy: Rusty Cundieff’s Fear of a Black Hat
8. Cannibal! The Musical
Troma Entertainment / Prod.DB / EAvenging Conscience / AlamySouth Park creators Matt Stone and Trey Parker’s inaugural feature film is a hysterically bizarre musical retelling of Alferd Packer’s disastrous and gruesome true story of desperation and death in the mountains of Colorado.
Where to Watch: Video-on-Demand
If you like this, you might also enjoy: Peter Jackson’s Meet the Feebles
9. Grosse Pointe Blank
Buena Vista Pictures / Courtesy Everett CollectionGeorge Armitage’s wonderfully wicked romantic comedy follows an unfocused professional assassin (John Cusack) who accepts a job adjacent to his 10-year high school reunion, prompting him to revisit an old flame (Minnie Driver) while worrying about a number of new enemies.
Where to Watch: Paramount+ & Tubi
If you like this, you might also enjoy: Thomas Schlamme’s So I Married an Axe Murderer
10. Used Cars
Columbia Pictures / Courtesy Everett CollectionKurt Russell headlines Robert Zemeckis’ superb 1980 ensemble comedy about competing used car dealerships that stoop to new outrageous lows to sabotage and embarrass one another through underhanded promotional tactics.
Where to Watch: Pluto TV
If you like this, you might also enjoy: Ron Howard’s Night Shift
11. Tucker & Dale vs. Evil
Maple Pictures / Courtesy Everett CollectionAlan Tudyk and Tyler Labine shine as two well-meaning backwoods boys who are erroneously painted as murderous rednecks after rescuing an injured young woman in Eli Craig’s spot-on send-up of slasher movies.
Where to Watch: Tubi
If you like this, you might also enjoy: Christopher Landon’s Freaky
12. Shakes the Clown
IRS Media / Courtesy Everett CollectionIn this passion project for director and star Bobcat Goldthwait, a habitually drunk party clown must clear his name after he is framed for the murder of his boss by a gang of felonious rivals.
Where to Watch: Video-on-Demand
If you like this, you might also enjoy: Danny DeVito’s Death to Smoochy
13. Jawbreaker
Tristar Pictures / Courtesy Everett CollectionRose McGowan, Judy Greer, Rebecca Gayheart, Julie Benz, and Pam Grier are all on point in Darren Stein’s demented dark comedy about a clique of teenage socialites who attempt to cover up an accidental murder as a result of a prank gone wrong.
Where to Watch: Tubi
If you like this, you might also enjoy: Michael Lehmann’s Heathers
14. Hot Rod
Paramount / Courtesy Everett CollectionThe Lonely Island’s underrated first film is not only a side-splitting exhibition of non-stop laughs but displayed the burgeoning comedic talents of costars Bill Hader and Danny McBride as well as a scene-stealing Ian McShane.
Where to Watch: Pluto TV
If you like this, you might also enjoy: Jorma Taccone’s MacGruber
15. Dirty Work
Universal / Courtesy Everett CollectionThe late, great Bob Saget and Norm Macdonald teamed up for this unforgettably twisted movie about two brothers who start a revenge-for-hire business in order to pay for their father’s emergency heart surgery.
Where to Watch: Tubi, YouTube, and the Roku Channel
If you like this, you might also enjoy: Evan Morgan’s The Kid Detective
16. The Ten
Think Film / Courtesy Everett CollectionWet Hot American Summer director David Wain’s sophomore feature is a raucous, star-studded comedy anthology featuring 10 intertwined stories, each of which surrounds one of the Ten Commandments.
Where to Watch: DVD/Blu-ray
If you like this, you might also enjoy: David Wain’s They Came Together
17. Welcome to the Dollhouse
Suburban Pictures / Entertainment Pictures / AlamyComedic provocateur Todd Solondz made an impact on the independent film scene with this biting coming-of-age comedy about a seventh grade girl who tries to find her place in the world among her wayward family, her degrading classmates, and the troublesome objects of her affection.
Where to Watch: HBO Max
If you like this, you might also enjoy: Bo Burnham’s Eighth Grade
18. Freddy Got Fingered
20th Century Fox / Courtesy Everett CollectionThe title alone should let you know if Tom Green’s transgressive feature film debut is your cup of tea, but if you think you’d love jaw-dropping shock humor underpinned by genuine good-natured optimism about life and family values, you just might be the perfect audience for this cult classic.
Where to Watch: Starz
If you like this, you might also enjoy: Kitao Sakurai’s Bad Trip
19. Romy and Michele’s High School Reunion
Buena Vista Pictures / Courtesy Everett CollectionDavid Mirkin’s gloriously unorthodox comedy follows a pair of aloof underachievers, played to hilarious perfection by Mira Sorvino and Lisa Kudrow, who decide that they want to change their lives around by perpetuating a giant lie at their high school reunion.
Where to Watch: Video-on-Demand
If you like this, you might also enjoy: Josh Greenbaum’s Barb and Star Go to Vista Del Mar
20. Kingpin
MGM / Courtesy Everett CollectionAfter the massive hit that was Dumb and Dumber, the Farrelly brothers delivered another comedic tour de force about a maimed former bowler (Woody Harrelson) that decides to mentor an Amish bowling prodigy (Randy Quaid), which puts the pair on the collision course with the sleazy yet esteemed bowler (Bill Murray) responsible for the former’s disfigurement.
Where to Watch: Showtime
If you like this, you might also enjoy: Jason Bateman’s Bad Words
21. Rubin & Ed
IRS Releasing / Courtesy Everett CollectionCrispin Glover and Howard Hesseman are an utterly delightful pairing in Trent Harris’ surreal and wacky buddy comedy about two misfits who journey into the desert to bury a frozen cat.
Where to Watch: DVD/Blu-ray
If you like this, you might also enjoy: Jocelyn DeBoer & Dawn Luebbe’s Greener Grass
22. Four Lions
Film4 Productions / Courtesy Everett CollectionBritish shockmaster Chris Morris had audiences gasping in between bursts of howling laughter in this button-pushing satirical comedy about bumbling suicide bombers featuring amazing early performances from The Night Of‘s Riz Ahmed and What We Do in the Shadows‘ Kayvan Novak.
Where to Watch: YouTube, Tubi and Amazon Prime
If you like this, you might also enjoy: Riley Stearns’ The Art of Self-Defense
23. Serial Mom
Universal Pictures / Courtesy Everett CollectionKathleen Turner is an absolute marvel in John Waters’ brilliant and bloody comedy about a housewife and mother who decides to keep up with the Joneses by murdering anyone who dare threaten her happy household.
Where to Watch: Starz
If you like this, you might also enjoy: Joe Dante’s The ‘Burbs
24. Black Dynamite
Apparition / Courtesy Everett CollectionMichael Jai White packs a heavy comedic punch in this painfully funny parody of blaxploitation action cinema that follows a kung fu-savvy vigilante who encounters drug dealers, ninjas, and a far-reaching government conspiracy while defending his community.
Where to Watch: Amazon Prime and the Roku Channel
If you like this, you might also enjoy: Keenen Ivory Wayans’ I’m Gonna Git You Sucka
25. Idiocracy
20th Century Fox / Courtesy Everett CollectionMike Judge’s unquestionably uproarious takedown of the future of American society may have been misunderstood by its studio upon its initial release, but has since become a stone-cold cult classic that becomes sadly more prescient as time goes on.
Where to Watch: YouTube and Tubi
If you like this, you might also enjoy: Don Coscarelli’s John Dies at the End
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