Funniest movies of the 90s

In no order whatsoever. Quit your complaining about 41 vs 42. Some of these movies are hybrid comedies/another genre, about 50/50%, and are still hilarious. Not a big Adam Sandler fan or Farrelly bros. fan; their movies make me chuckle, not laugh. As to whether I "know" about cinema or if I am ignorant because I do not laugh at the same, I have watched 3000 movies, from indie, to pretentious psuedo-art flicks, to B-movies and Z-movies and the MST3K-able, to mainstream blockbusters, the award nominees, and movies from every continent and most major language. Name your cult director, I've watched their film. The real question is... why take comedy seriously?
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1.
Clerks (1994)
    1 2 3 4 5 6 7 8 9 10 7.8/10 X  
A day in the lives of two convenience clerks named Dante and Randal as they annoy customers, discuss movies, and play hockey on the store roof. (92 mins.)
Director: Kevin Smith
 
2.
My Fellow Americans (1996)
    1 2 3 4 5 6 7 8 9 10 6.5/10 X  
Two former U. S. Presidents, hated rivals, join forces to expose the current, corrupt President at the risk of their lives. (101 mins.)
Director: Peter Segal
 
3.
Austin Powers: International Man of Mystery (1997)
    1 2 3 4 5 6 7 8 9 10 7.0/10 X  
A 1960s hipster secret agent is brought out of cryofreeze to oppose his greatest enemy in the 1990s, where his social attitudes are glaringly out of place. (94 mins.)
Director: Jay Roach
 
4.
South Park: Bigger Longer & Uncut (1999)
    1 2 3 4 5 6 7 8 9 10 7.8/10 X  
When the four boys see an R-rated movie featuring Canadians Terrance & Phillip, they are pronounced "corrupted", and their parents pressure the United States to wage war against Canada. (81 mins.)
Director: Trey Parker
 
5.
Scream (1996)
    1 2 3 4 5 6 7 8 9 10 7.2/10 X  
Sidney, attempting to cope with her mother's mysterious murder, and her horror movie-obsessed friends are stalked by an unknown killer who seems to have a hard time letting the past go. (111 mins.)
Director: Wes Craven
“ A hilarious satire of horror movies, while still being a straight, stylish, scary horror movie. Lillard and Kennedy provide most of the laughs, and Williamson's script is highly quotable. People laugh and scream while watching this. The hybrid angle confused critics, who gave it bad reviews upon release. A year later, after they were shown to be fools by the cult following of people who understood what it was, they gave its sequel very positive reviews. ” - demented_peruvian
 
6.
Hero (1992)
    1 2 3 4 5 6 7 8 9 10 6.5/10 X  
A not-so-nice man rescues passengers from a crashed airliner, only to see someone else take credit. (119 mins.)
Director: Stephen Frears
 
7.
Groundhog Day (1993)
    1 2 3 4 5 6 7 8 9 10 8.1/10 X  
A weatherman finds himself living the same day over and over again. (101 mins.)
Director: Harold Ramis
 
8.
The Big Lebowski (1998)
    1 2 3 4 5 6 7 8 9 10 8.2/10 X  
"The Dude" Lebowski, mistaken for a millionaire Lebowski, seeks restitution for his ruined rug and enlists his bowling buddies to help get it. (117 mins.)
Director: Joel Coen
 
9.
The Naked Gun 2½: The Smell of Fear (1991)
    1 2 3 4 5 6 7 8 9 10 6.8/10 X  
Lieutenant Drebin discovers that his ex-girlfriend's new beau is involved in a plot to kidnap a scientist who advocates solar energy. (85 mins.)
Director: David Zucker
 
10.
Hot Shots! (1991)
    1 2 3 4 5 6 7 8 9 10 6.7/10 X  
A parody of Top Gun in which a talented but unstable fighter pilot must overcome the ghosts of his father and save a mission sabotaged by greedy weapons manufacturers. (84 mins.)
Director: Jim Abrahams
 
11.
Tommy Boy (1995)
    1 2 3 4 5 6 7 8 9 10 7.0/10 X  
An incompetent, immature, and dimwitted heir to an auto parts factory must save the business to keep it out of the hands of his new, con-artist relatives and big business. (97 mins.)
Director: Peter Segal
 
12.
Hot Shots! Part Deux (1993)
    1 2 3 4 5 6 7 8 9 10 6.6/10 X  
"Rambo" parody in which Topper Harley leads a rescue team into Iraq to save Iraqi war prisoners and all of their previous rescue teams. (86 mins.)
Director: Jim Abrahams
 
13.
Mallrats (1995)
    1 2 3 4 5 6 7 8 9 10 7.2/10 X  
Both dumped by their girlfriends, two best friends seek refuge in the local mall. (94 mins.)
Director: Kevin Smith
 
14.
Robin Hood: Men in Tights (1993)
    1 2 3 4 5 6 7 8 9 10 6.7/10 X  
A spoof of Robin Hood in general and Robin Hood: Prince of Thieves in particular. (104 mins.)
Director: Mel Brooks
 
15.
Ed Wood (1994)
    1 2 3 4 5 6 7 8 9 10 7.9/10 X  
An ambitious but troubled movie director tries his best to fulfill his dream, despite his lack of support. (127 mins.)
Director: Tim Burton
“ Yes, it has dramatic moments, but it is mostly played as a sweet comedy. ” - demented_peruvian
 
16.
Dazed and Confused (1993)
    1 2 3 4 5 6 7 8 9 10 7.7/10 X  
The adventures of high school and junior high students on the last day of school in May 1976. (102 mins.)
“ Mostly comedy, some drama about coming of age, still hilarious overall. ” - demented_peruvian
 
17.
Mrs. Doubtfire (1993)
    1 2 3 4 5 6 7 8 9 10 6.9/10 X  
After a bitter divorce, an actor disguises himself as a female housekeeper to spend time with his children held in custody by his former wife. (125 mins.)
Director: Chris Columbus
 
18.
Chasing Amy (1997)
    1 2 3 4 5 6 7 8 9 10 7.4/10 X  
Holden and Banky are comic book artists. Everything's going good for them until they meet Alyssa, also a comic book artist. Holden falls for her, but his hopes are crushed when he finds out she's gay. (113 mins.)
Director: Kevin Smith
 
19.
Clueless (1995)
    1 2 3 4 5 6 7 8 9 10 6.8/10 X  
A rich high school student tries to boost a new pupil's popularity, but reckons without affairs of the heart getting in the way. (97 mins.)
Director: Amy Heckerling
 
20.
Boogie Nights (1997)
    1 2 3 4 5 6 7 8 9 10 7.9/10 X  
The story of a young man's adventures in the Californian pornography industry of the late 1970s and early 1980s. (155 mins.)
“ Yes, there's drama and suspense, but also a lot of very dark humor. Audiences would alternate between laughing and being stunned. ” - demented_peruvian
 
21.
Sister Act (1992)
    1 2 3 4 5 6 7 8 9 10 6.2/10 X  
When a worldly singer witnesses a mob crime, the police hide her as a nun in a traditional convent where she has trouble fitting in. (100 mins.)
Director: Emile Ardolino
 
22.
City Slickers (1991)
    1 2 3 4 5 6 7 8 9 10 6.7/10 X  
On the verge of turning 40, an unhappy Manhattan yuppie is roped into joining his two friends on a cattle drive in the southwest. (113 mins.)
Director: Ron Underwood
 
23.
Dave (1993)
    1 2 3 4 5 6 7 8 9 10 6.8/10 X  
To avoid a potentially explosive scandal when the U.S. President goes into a coma, an affable temp agency owner with an uncanny resemblance, is put in his place. (110 mins.)
Director: Ivan Reitman
 
24.
The Mask (1994)
    1 2 3 4 5 6 7 8 9 10 6.9/10 X  
Bank clerk Stanley Ipkiss is transformed into a manic superhero when he wears a mysterious mask. (101 mins.)
Director: Charles Russell
 
25.
Ace Ventura: Pet Detective (1994)
    1 2 3 4 5 6 7 8 9 10 6.9/10 X  
A goofy detective specializing in animals goes in search of a missing dolphin mascot of a football team. (86 mins.)
Director: Tom Shadyac
 
26.
Bowfinger (1999)
    1 2 3 4 5 6 7 8 9 10 6.4/10 X  
When a desperate movie producer fails to get a major star for his bargain basement film, he decides to shoot the film secretly around him. (97 mins.)
Director: Frank Oz
 
27.
As Good as It Gets (1997)
    1 2 3 4 5 6 7 8 9 10 7.7/10 X  
A single mother/waitress, a misanthropic author, and a gay artist form an unlikely friendship after the artist is assaulted in a robbery. (139 mins.)
Director: James L. Brooks
 
28.
American Beauty (1999)
    1 2 3 4 5 6 7 8 9 10 8.4/10 X  
A sexually frustrated suburban father has a mid-life crisis after becoming infatuated with his daughter's best friend. (122 mins.)
Director: Sam Mendes
“ Hilarious how people now consider this a drama, just because it won Oscars. Remember that it also won comedy awards? Audiences cried at the end, but laughed all the way through Kevin Spacey's opening monologue, boss blackmail, suburban satire, and "Re-Animator" references. ” - demented_peruvian
 
29.
American Pie (1999)
    1 2 3 4 5 6 7 8 9 10 7.0/10 X  
Four teenage boys enter a pact to lose their virginity by prom night. (95 mins.)
Director: Paul Weitz
 
30.
Rush Hour (1998)
    1 2 3 4 5 6 7 8 9 10 6.9/10 X  
Two cops team up to get back a kidnapped daughter. (98 mins.)
Director: Brett Ratner
“ It's an action movie done by comedians. ” - demented_peruvian
 
31.
Class Act (1992)
    1 2 3 4 5 6 7 8 9 10 6.0/10 X  
Duncan is a genius straight A student, Blade is juvenile delinquent. But because of a mix up with their school records... (98 mins.)
Director: Randall Miller
 
32.
Loaded Weapon 1 (1993)
    1 2 3 4 5 6 7 8 9 10 6.1/10 X  
An LA detective is murdered because she has microfilm with the recipe to make cocaine cookies. A "Lethal... (84 mins.)
Director: Gene Quintano
 
33.
Oscar (1991)
    1 2 3 4 5 6 7 8 9 10 6.4/10 X  
A gangster attempts to keep the promise he made to his dying father: that he would give up his life of crime and "go straight". (109 mins.)
Director: John Landis
“ It got a bad rep due to Stallone haters, mocking his turn to comedy. Actually, it is one of John Landis' funniest; a throwback to classic movie comedy. ” - demented_peruvian
 
34.
Fight Club (1999)
    1 2 3 4 5 6 7 8 9 10 8.8/10 X  
An insomniac office worker, looking for a way to change his life, crosses paths with a alter-ego devil-may-care soap maker, forming an underground fight club that evolves into something much, much more... (139 mins.)
Director: David Fincher
 
35.
Wayne's World 2 (1993)
    1 2 3 4 5 6 7 8 9 10 6.1/10 X  
The inseparable duo try to organize a rock concert while Wayne must fend off a record producer who has an eye for his girlfriend. (95 mins.)
Director: Stephen Surjik
 
36.
Wayne's World (1992)
    1 2 3 4 5 6 7 8 9 10 7.0/10 X  
Two slacker friends try to promote their public-access cable show. (94 mins.)
 
37.
So I Married an Axe Murderer (1993)
    1 2 3 4 5 6 7 8 9 10 6.4/10 X  
A San Francisco poet who fears commitment has a girlfriend who he suspects may not be who she appears. (93 mins.)
Director: Thomas Schlamme
 
38.
Singles (1992)
    1 2 3 4 5 6 7 8 9 10 6.7/10 X  
A group of twenty-something friends, most of whom live in the same apartment complex, search for love and success in grunge-era Seattle. (99 mins.)
Director: Cameron Crowe
 
39.
Office Space (1999)
    1 2 3 4 5 6 7 8 9 10 7.8/10 X  
Three company workers who hate their jobs decide to rebel against their greedy boss. (89 mins.)
Director: Mike Judge
 
40.
True Lies (1994)
    1 2 3 4 5 6 7 8 9 10 7.2/10 X  
A fearless, globe-trotting, terrorist-battling secret agent has his life turned upside down when he discovers his wife might be having an affair with a used car salesman. (141 mins.)
Director: James Cameron
“ It's an all-out comedy (a remake of a French farce!) with guns and planes thrown in the mix. Even the action sequences are so outrageous that they are funny. ” - demented_peruvian
 
41.
Stay Tuned (1992)
    1 2 3 4 5 6 7 8 9 10 6.0/10 X  
A husband and wife are sucked into a hellish TV and have to survive a gauntlet of twisted versions of TV shows they find themselves in. (88 mins.)
Director: Peter Hyams
 
42.
Delirious (1991)
    1 2 3 4 5 6 7 8 9 10 5.7/10 X  
A soap opera writer gets hit on the head and wakes up as a character in his own show. (96 mins.)
Director: Tom Mankiewicz
 
43.
Cannibal! The Musical (1993)
    1 2 3 4 5 6 7 8 9 10 7.2/10 X  
The sole survivor of an ill-fated mining expedition tells how his taste for gold was replaced by that of human flesh. (95 mins.)
Director: Trey Parker
 
44.
Orgazmo (1997)
    1 2 3 4 5 6 7 8 9 10 6.2/10 X  
Naive young Mormon Joe Young is recruited to act in porn movies. (94 mins.)
Director: Trey Parker
 
45.
Beavis and Butt-Head Do America (1996)
    1 2 3 4 5 6 7 8 9 10 6.8/10 X  
The dim-witted teen duo of Beavis and Butt-Head travel across America in search of their stolen television set. (81 mins.)
 
46.
Forrest Gump (1994)
    1 2 3 4 5 6 7 8 9 10 8.8/10 X  
Forrest Gump, while not intelligent, has accidentally been present at many historic moments, but his true love, Jenny Curran, eludes him. (142 mins.)
Director: Robert Zemeckis
 
47.
Private Parts (1997)
    1 2 3 4 5 6 7 8 9 10 6.8/10 X  
The autobiographical story of Howard Stern, the radio rebel who is now also a TV personality, an author and a movie star. (109 mins.)
Director: Betty Thomas
 
48.
Being John Malkovich (1999)
    1 2 3 4 5 6 7 8 9 10 7.8/10 X  
A puppeteer discovers a portal that leads literally into the head of movie star John Malkovich. (112 mins.)
Director: Spike Jonze
 
49.
Living in Oblivion (1995)
    1 2 3 4 5 6 7 8 9 10 7.6/10 X  
Film about filmmaking. It takes place during one day on set of non-budget movie. Ultimate tribute to all independent filmmakers. (90 mins.)
Director: Tom DiCillo
 
50.
Flirting with Disaster (1996)
    1 2 3 4 5 6 7 8 9 10 6.8/10 X  
A young man, his wife, and his incompetent case worker travel across country to find his birth parents. (92 mins.)
 
51.
Swingers (1996)
    1 2 3 4 5 6 7 8 9 10 7.4/10 X  
Wannabe actors become regulars in the stylish neo-lounge scene; Trent teaches his friend Mike the unwritten rules of the scene. (96 mins.)
Director: Doug Liman
 
52.
Maverick (1994)
    1 2 3 4 5 6 7 8 9 10 7.0/10 X  
Bret Maverick, needing money for a poker tournament, faces various comic mishaps and challenges, including a charming woman thief. (127 mins.)
Director: Richard Donner
 
53.
Man on the Moon (1999)
    1 2 3 4 5 6 7 8 9 10 7.4/10 X  
The life and career of a legendary comedian, Andy Kaufman. (118 mins.)
Director: Milos Forman
 
54.
Bill & Ted's Bogus Journey (1991)
    1 2 3 4 5 6 7 8 9 10 6.2/10 X  
A tyrant from the future creates evil android doubles of Bill and Ted and sends them back to eliminate the originals. (93 mins.)
Director: Pete Hewitt
 
55.
PCU (1994)
    1 2 3 4 5 6 7 8 9 10 6.5/10 X  
A high school senior visits college for the weekend, and stays at the wildest house on campus in this classic tale of anti-political-correctness. (79 mins.)
Director: Hart Bochner
 
56.
If Looks Could Kill (1991)
    1 2 3 4 5 6 7 8 9 10 5.7/10 X  
When Michael Corben, along with the rest of his high-school French class, set out for a trip to France... (88 mins.)
Director: William Dear
 
57.
Go (1999)
    1 2 3 4 5 6 7 8 9 10 7.3/10 X  
Go! tells the story of the events after a drug deal, told from three different points of view. (102 mins.)
Director: Doug Liman
 
58.
Six-String Samurai (1998)
    1 2 3 4 5 6 7 8 9 10 6.7/10 X  
In the post-apocalyptic world of 1960s Nevada, a rock 'n' roll samurai takes a young boy under his protection. (91 mins.)
Director: Lance Mungia
 
59.
Mystery Science Theater 3000: The Movie (1996)
    1 2 3 4 5 6 7 8 9 10 7.4/10 X  
Mike Nelson and his robot companions watch and give their comments about This Island Earth. (73 mins.)
Director: Jim Mallon
 
60.
Erik the Viking (1989)
    1 2 3 4 5 6 7 8 9 10 6.2/10 X  
Erik the Viking and his men travel across the sea to find Valhalla to ask the gods to end the Age of Ragnarok. (107 mins.)
Director: Terry Jones
 
61.
Waiting for Guffman (1996)
    1 2 3 4 5 6 7 8 9 10 7.6/10 X  
An aspiring director and the marginally talented amateur cast of a hokey small-town Missouri musical production go overboard when they learn that someone from Broadway will be in attendance. (84 mins.)
“ The last hour was so-so, but the first 30 minutes were hilarious. ” - demented_peruvian
 
62.
The Full Monty (1997)
    1 2 3 4 5 6 7 8 9 10 7.2/10 X  
Six unemployed steel workers form a male striptease act. The women cheer them on to go for "the full monty" - total nudity. (91 mins.)
Director: Peter Cattaneo
“ A funny movie about depressing circumstances. ” - demented_peruvian