Whether you're feeling nostalgic for the days when comedies were a little less PG-13 or just curious to see how far the 90s really went, this list has got you covered.
20. "Deuce Bigalow: Male Gigolo" (1999)
Rotten Tomatoes score: 22%
An awkward fish tank cleaner becomes a male gigolo to earn quick cash after wrecking the house of a gigolo, leading him through a series of comical and bizarre encounters with his clients.
19. "Half Baked" (1998)
Rotten Tomatoes score: 28%
Four stoner friends come up with ridiculous schemes to bail their friend out of jail after he accidentally kills a police horse while high, leading to a series of misadventures involving a medical marijuana heist.
18. "The Waterboy" (1998)
Rotten Tomatoes score: 33%
A socially awkward, waterboy for a college football team discovers he has a unique tackling ability and becomes a member of the team, leading to newfound confidence, success, and confrontations with his overprotective mother.
17. "Tommy Boy" (1995)
Rotten Tomatoes score: 39%
After his father's sudden death, an inept and clumsy son must save the family auto parts factory from bankruptcy, teaming up with his father's savvy assistant on a cross-country sales trip full of misadventures.
16. "Very Bad Things" (1998)
Rotten Tomatoes score: 41%
A Las Vegas bachelor party goes horribly wrong when a prostitute is accidentally killed, leading the attendees into a downward spiral of panic, cover-up, and increasingly poor decisions.
15. "BASEketball" (1998)
Rotten Tomatoes score: 41%
Two childhood friends invent a game combining basketball and baseball, which becomes a national sport, leading them to deal with fame, fortune, and the threat of their sport being corrupted by corporate interests.
14. "Orgazmo" (1997)
Rotten Tomatoes score: 48%
A naïve Mormon missionary gets roped into the pornographic film industry but becomes a superhero in a pornographic movie, leading to unexpected fame and a conflict with his moral values and newfound career.
13. "Kingpin" (1996)
Rotten Tomatoes score: 49%
A once-promising bowler who loses his hand turns to a naive Amish prodigy to win a national bowling tournament, leading them both through a series of humorous and heartwarming misadventures in the professional bowling world.
12. "The Cable Guy" (1996)
Rotten Tomatoes score: 55%
A lonely, odd cable guy with a murky past befriends a customer, leading to a bizarre and increasingly obsessive relationship that spirals out of control as the cable guy's true nature is revealed.
11. "Mallrats" (1995)
Rotten Tomatoes score: 58%
Two recently dumped friends seek solace and revenge in a local mall, encountering a series of eccentric characters, leading to an absurd series of events including a dating game show, comic book artists, and a mall security chase.
10. "American Pie" (1999)
Rotten Tomatoes score: 61%
In this coming-of-age comedy, four high school boys enter a pact to lose their virginity by prom night, leading them through a series of hilarious, often embarrassing, and revealing experiences that challenge their understanding of friendship, love, and sex.
9. "Happy Gilmore" (1996)
Rotten Tomatoes score: 62%
A failed hockey player with a powerful golf swing joins the professional golf tour to save his grandmother's house, bringing his unconventional style and temper to the staid world of golf.
8. "Dogma" (1999)
Rotten Tomatoes score: 68%
Two fallen angels manipulate a religious loophole to re-enter Heaven, potentially undoing existence, prompting an abortion clinic worker with a special lineage to stop them with the help of various unconventional allies, including a muse, two prophets, and the thirteenth apostle.
7. "Dumb and Dumber" (1994)
Rotten Tomatoes score: 68%
Two well-meaning but incredibly dimwitted friends embark on a cross-country road trip to return a briefcase full of money to its owner, unaware it is connected to a kidnapping, leading to absurd situations and unintentional heroics.
6. "Austin Powers: International Man of Mystery" (1997)
Rotten Tomatoes score: 73%
In a spoof of 1960s spy films, the flamboyant and quirky British secret agent Austin Powers is thawed from his cryogenic state to battle his nemesis Dr. Evil in the 1990s, leading to a comedic clash of cultural and temporal differences.
5. "South Park: Bigger, Longer & Uncut" (1999)
Rotten Tomatoes score: 80%
When the children of South Park see a controversial R-rated Canadian film, their parents' outrage sparks a global conflict with Canada, leading to an outrageous musical satire that tackles issues of censorship, war, and adolescence.
4. "The Big Lebowski" (1998)
Rotten Tomatoes score: 80%
The story of "The Dude" Lebowski, a laid-back, easygoing burnout who gets entangled in a convoluted kidnapping plot involving mistaken identity, a millionaire, nihilists, and a missing ransom, all while just trying to get his beloved rug replaced.
3. "Office Space" (1999)
Rotten Tomatoes score: 80%
A disillusioned office worker frustrated with his mundane job and his obnoxious boss undergoes a life-changing epiphany and conspires with his co-workers to embezzle money from the company, leading to a series of comedic and unexpected consequences.
2. "There's Something About Mary" (1998)
Rotten Tomatoes score: 84%
A man still smitten with his high school crush hires a private detective to track her down, only to have the detective fall for her too, leading to a series of comedic misunderstandings and rivalries, all centered around the charming and oblivious Mary.
1. "Clerks" (1994)
Rotten Tomatoes score: 90%
A day in the life of two store clerks, Dante and Randal, as they converse about life, deal with eccentric customers, and question their life choices, all the while showcasing the banality and absurdity of retail work.