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Was the last decade of the 20th Century its funniest? The greatest comedies of the 1990s certainly make a compelling—and side-splitting—case. This was an era when audiences would turn out in droves to have their funny bones tickled at the cineplex, and the comedies frequently topped the box office.
There was a wide variety of comedies in the '90s, too. Gross-out teen comedies played alongside riffs on other genres, like sci-fi parodies or silly sports tales. Rom-coms were arguably never better than they were in this decade, and you had stars like Jim Carrey, Mike Myers, Robin Williams, Adam Sandler, and Julia Roberts providing audiences with reliable laughs—and, on occasion, maybe even some well-earned tears, too.
So get ready to giggle, guffaw, and chortle at the 32 best comedy movies of the 1990s.
32. The Mask
Year: 1994
Director: Chuck Russell
"Somebody Stop Me!" No actor defined '90s comedies as much as Jim Carrey, who in 1994 alone starred in three iconic romps; Ace Ventura: Pet Detective, Dumber and Dumber, and The Mask. The Mask might be Carrey at his most unhinged, as the enchanted mask that turns him into the titular green horndog swing enthusiast lets him really fly his freak flag. The Mask is a "smokin'!" comedy that really could've only been made in the mid-'90s, for better or worse.
31. Robin Hood Men in Tights
Year: 1993
Director: Mel Brooks
A lesser Mel Brooks comedy is still better than most movies, and his take on the Robin Hood legend, starring Cary Elwes as the emerald archer, is a charmingly silly—occasionally dumb—good time. Men in Tights is at its best when it leans into that goofiness, gleefully inviting anachronisms or making the whole thing into a farce, such as when Robin checks the script (of the movie he's currently in) to confirm that he's not supposed to lose an archery contest. A young Dave Chappelle co-stars as one of Robin's Merry Men.
30. Arachnophobia
Year: 1990
Director: Frank Marshall
Horror-comedies are deceptively tricky to pull off, as far too often a movie will either be too far in one direction or the other; either too silly to take the scares seriously or so spooky that the jokes feel out of place. Much like Jeff Daniels with a nail gun during the film's climax, Arachnophobia nails it. The spiders are legitimately creepy crawlies, but there are tons of laughs to be found in its portrayal of American suburbia—and especially John Goodman's over-the-top exterminator character.
29. Happy Gilmore
Year: 1996
Director: Dennis Dugan
He's gone on to bigger and better things, but for anybody who was around in the '90s, this is the decade that will always be Adam Sandler's peak. The Sandman starred in a lot of comedies at the start of his career, where he played a boisterous loudmouth who was sort of a dummy but had a heart of gold. Happy Gilmore, where he plays a failed hockey player who discovers he has an unorthodox knack for golf, is a beloved cult classic—and it's not a bad sports movie, either.
28. American Pie
Year: 1999
Director: Paul Weitz
This teen coming-of-age flick revived a whole raunchy comedy subgenre, following a group of high school students who are all trying to lose their virginity before they graduate and go off to college. Gross out gags, lusty discussions about Stifler's Mom, the desecration of a baked good, and a surprising amount of sentimentality ensue. American Pie spawned a ton of sequels, but despite the consistent presence of Eugene Levy in most of 'em, none approached the heights of the original.
27. Death Becomes Her
Year: 1992
Director: Robert Zemeckis
Meryl Streep and Goldie Hawn star as a pair of frenemies who, after an ugly falling out, attempt to one-up and outdo each other. A contest that culminates in both of them drinking a potion that makes them immortal ensues… but it turns out that being a walking zombie has some downsides. Death Becomes Her is an incredible achievement in special effects (scenes where Streep's head is twisted backwards or Hawn has a big hole in the middle of her body look simple now, but were, in fact, wildly advanced for the time), and it's also a darkly funny morality tale.
26. Billy Madison
Year: 1995
Director: Tamra Davis
Adam Sandler's first movie as the lead and main character is arguably the best of his beloved '90s output. In Billy Madison, Sandler plays the title character, a very immature man who stands to inherit his father's company and vast wealth—but only if he can grow up a little bit and prove himself by completing grades 1 through 12. Right off the bat, Sandler's boorish charm is in full display, and he benefits from playing opposite Bradley Whitford, who, as Billy's rival for the inheritance, is one of the all-time movie snobs.
25. Mystery Men
Year: 1999
Director: Kinka Usher
A parody of superheroes that arrived several years before superheroes became the hottest thing at the box office, Mystery Men stars Ben Stiller, Hank Azaria, and William H. Macy as trio of Z-list crime fighters who suddenly become Champion City's only hope after the supervillain Casanova Frankenstein (Geoffrey Rush) bests the egotistical top dog superhero, Captain Amazingly (Greg Kinnear). Extremely clever, Mystery Men probably holds up better today than it did back in '99. (Fun fact: Although associated with Shrek, Smash Mouth's "All Star" made its film debut in Mystery Men, and clips from the movie featured in the official music video.)
24. A League of Their Own
Year: 1992
Director: Penny Marshall
"There's no crying in baseball!" One of the best sports movies, Penny Marshall's A League of Their Own, follows the fictionalized tale of the Rockford Peaches, an all-girls baseball team that competed during World War II while most of the men were overseas fighting in the war. Anchored by a winning performance by Geena Davis and featuring scene-stealing (and base-stealing, literally) turns from Lori Petti, Rosie O'Donnell, and Madonna, plus Tom Hanks as their manager, it's an all-time classic.
23. Dumb and Dumber
Year: 1994
Director: Peter Farrelly
You've got to love the '90s, an era when the premise "what if two friends were really dumb?" was enough to greenlight a movie and to have it be a smash hit. Jim Carrey and Jeff Daniels star as Lloyd and Harry, a pair of dopes who set out for Aspen in the hopes of doing a good deed and returning a briefcase full of money they found—but they have no clue that they've actually gotten themselves wrapped up in a ransom situation. It's not the most intellectual comedy of the '90s, but with a name like that… would you want it to be?
22. Clerks
Year: 1994
Director: Kevin Smith
Jay and Silent Bob (Jason Mewes and director Kevin Smith) make their debut in Clerks, the start of Smith's View Askewniverse and one of the most celebrated indie comedies of the decade. Dante Hicks (Brian O'Halloran) and Randal Graves (Jeff Anderson) work as clerks in a New Jersey mall, and the movie follows them and a few of their friends throughout a day—much of which is spent doing things like arguing which Star Wars movie has the better ending. Witty, scrappy, and relatable, Clerks is an icon of slacker cinema.
21. Toy Story
Year: 1995
Director: John Lasseter
The first Pixar movie is known for revolutionizing animation, but in addition to being a breakthrough in computer animation, Toy Story is also really funny on a level that kids and adults alike can enjoy. Starring the voice talents of Tom Hanks as the cowboy doll Woody and Tim Allen as the space ranger action figure Buzz Lightyear—who doesn't believe he's a toy at all —Toy Story's short 81-minute runtime is overflowing with funny visuals, charming characters, and killer line deliveries ("You! Are a child's! Plaything!").
20. Home Alone
Year: 1990
Director: Chris Columbus
As one of the best Christmas movies that many people watch every single year when the holidays come around, it's nice that Home Alone is legitimately very funny even once you've lost count of what number rewatch you're on. Macaulay Culkin stars as Kevin, a kid who has been accidentally left behind on Christmas but is making the best of it—until the Wet Bandits (Joe Pesci and Daniel Stern) target his house. There's Christmas magic and comical violence, as watching Harry and Marv get bonked in the head yet or suffer multiple injuries in a row that could all be fatal, never gets old.
19. Pretty Woman
Year: 1990
Director: Garry Marshall
Would Pretty Woman have become the runaway success and blockbuster smash it was had it been a darker story about the escort business, as was the original pitch? Probably not, and everyone is better off with the lighthearted rom-com we got that showcases Julia Roberts' dazzling charm and charisma, playing a lady of the night who develops a real relationship with Richard Gere's executive after he hires her for a week. Pretty Woman cemented Roberts' stardom, and it's easy to see why.
18. Bowfinger
Year: 1999
Director: Frank Oz
One of the great (if underappreciated) movies about Hollywood, Bowfingers stars Steve Martin as Bobby Bowfinger, a low-rent filmmaker who is trying to make a low-budget sci-fi movie featuring big movie star Kit Ramsey (Eddie Murphy) in the lead role. The catch is that Ramsey didn't agree to be in the movie and doesn't know they're making it, so Bowfinger and his team must try to shoot the film around Ramsey without him knowing. A spot-on celebration of the scrappy side of the movie industry, Bowfinger should be an outright classic rather than a cult classic.
17. Liar Liar
Year: 1997
Director: Tom Shadyac
Comedies in the '90s were full of workaholic dads who needed to go through a crazy experience to learn how to reconnect with their kids (see also: Hook, and Mrs. Doubtfire). Jim Carrey stars as one in Liar Liar, playing Fletcher Reede, a Los Angeles divorce attorney who becomes unable to lie for 24 hours after his son makes a birthday wish. Carrey has an innate ability to contort his face like a live-action cartoon, and Liar Liar puts this talent to great use as an increasingly flustered Fletcher tries and fails to fib.
16. Dogma
Year: 1999
Director: Kevin Smith
The fourth movie in Kevin Smith's View Askewniverse is a huge escalation from the earlier ones, which mostly followed groups of slackers. There are still slackers in Dogma, but now they're finding themselves caught up in a mess of biblical proportions—literally—as they need to stop two fallen angels (Ben Affleck and Matt Damon) from entering a church and, in doing so, regaining access to heaven, undoing all of creation. Though epic in its premise, Dogma still radiates Smith's off-beat humor. Controversial when it was first released, Dogma's reputation only grew when, for many years, rights issues made it essentially impossible to watch.
15. Mars Attacks!
Year: 1996
Director: Tim Burton
A feature film adaptation of an enthusiastically violent and gory trading card series from the '60s about an alien invasion, Mars Attacks! is an irrelevant celebration of retro sci-fi with a heavy dose of kitsch and an appetite for destruction. Boasting grotesque chattering martians, comical body horror, a star-studded cast that boasts Jack Nicholson playing not one but two unrelated roles for some reason, and a satirical spin on well-worn genre tropes, Mars Attacks! is one of Tim Burton's most under-sung films.
14. She's All That
Year: 1999
Director: Robert Iscove
George Bernard Shaw's play Pygmalion, previously adapted into a movie as My Fair Lady, gets a SoCal high school makeover in She's All That, starring Freddie Prinze Jr. and Rachael Leigh Cook as a pair of students. Zack (Prinze) is the most popular kid in school, and he makes a bet that he can turn the lamest girl in the class, Laney Boggs (Cook), into a prom queen in just six weeks. Naturally, in addition to laughs, some real feelings between them emerge. She's All That is full of tropes that you've seen countless times before in high school movies before and since, but it pulls them off really, really well.
13. Men in Black
Year: 1997
Director: Barry Sonnenfeld
Here's a hot take: Men in Black is a better movie than Ghostbusters. Both films have similar premises, following a group of people who deal with strange phenomenons in New York City—while most New Yorkers don't really bat an eye. Rather than ghosts, Tommy Lee Jones and Will Smith's Agents K and J are members of the top-secret, ultra-classified agency that monitors and polices the many aliens that come to Earth. There's action, good special effects, Smith's undeniable charisma, and an absolutely incredible turn from Vincent D'Onofrio as a bug alien who inhabits the body of a farmer. "Sugar water."
12. My Cousin Vinny
Year: 1992
Director: Jonathan Lynn
In addition to having lots of great comedies, the '90s were full of fantastic legal dramas, and My Cousin Vinny just so happens to be both. Joe Pesci stars as the titular Vinny, a loud-mouth New Yorker who has just passed the bar, who, along with his wife Mona Lisa (a delightful Marisa Tomei), comes to rural Alabama to help his cousin and his friend try to avoid being wrongfully convicted of a murder they didn't commit. It's a great fish-out-of-water story with laughs and captivating courtroom scenes.
11. The Truman Show
Year: 1998
Director: Peter Weir
Jim Carrey plays Truman Burbank, a man who doesn't realize that his entire life has been a live-broadcast reality show documenting his every move in one of the decade's most prescient and most philosophical films—that also happens to be quite funny, too. Carrey, playing in a more serious register than a lot of his other '90s credits like Ace Ventura or The Mask, but still getting chances to be goofy, is stellar. Laura Linney, who plays Truman's wife (or really plays an actor who is playing the role of Truman's wife), might be the comedy standout for the ways she's tasked with inserting product placement into normal everyday conversations.
10. Notting Hill
Year: 1999
Director: Roger Michell
Julia Roberts and Hugh Grant star in one of the most beloved rom-coms of the decade, which follows a book shop owner (Grant) in London's Notting Hill district who unexpectedly begins a relationship with a famous American actress (Roberts) after they have a meet-cute when she pops into his store. An absolutely charming fairy tale, Notting Hill explores the meeting of fame and feelings, and Grant and Roberts are both as charismatic and likeable as they've ever been—which is saying something.
9. Mrs. Doubtfire
Year: 1993
Director: Chris Columbus
The best of the many comedies of the era to deal with divorce, Mrs. Doubtfire stars Robin Williams as an actor who, wanting to spend more time with his kids, adopts the identity of Euphegenia Doubtfire, an elderly British woman whom his ex-wife (Sally Field) hires as a nanny. Beyond just the comedy of seeing Williams dress in drag and do silly voices, Mrs. Doubtfire has zany antics as he tries to keep up the ruse. Still, there's ultimately a very heartfelt message about the enduring—if changing—nature of families behind the deception.
8. Gremlins 2: The New Batch
Year: 1992
Director: Joe Dante
Gremlins 2: The New Batch is a triumph of cinema. Director Joe Dante took the essentially blank creative check he'd been given to make a sequel to his '80s horror flick (that had some comedy elements) and used it to make a gonzo commentary on the nature of sequels themselves. Moving the action from a picturesque suburb to the Big Apple, Gremlins 2 is full of all sorts of different types of monsters and mayhem; the uniting aspect of all the chaos being a voracious desire to tear down tropes.
7. South Park: Bigger, Longer, and Uncut
Year: 1999
Director: Trey Parker
The best musical of the 1990s, South Park: Bigger, Longer, and Uncut, is foul-mouthed and funny as heck. A big screen take on Matt Stone and Trey Parker's Comedy Central cartoon, the South Park movie followed Stan, Kyle, Cartman, and Kenny after a Canadian movie prompts them to start using curse words, setting off a chain of events that lead to a war with their neighbors to the north and the Devil and his lover, Sadam Hussein, trying to conquer the world. Proudly profane and full of great songs in addition to its great jokes (like the Oscar-nominated "Blame Canada"), the movie is a high point for the long-running series.
6. Galaxy Quest
Year: 1999
Director: Dean Parisot
With all due respect to Wrath of Khan, Galaxy Quest is the best Star Trek movie despite not technically being, well, a Star Trek movie. It might as well be, though, as it's a hysterical and exciting love letter to Trekkies and fandom. Tim Allen stars as a very Shatner-like actor who use to star in a cult classic sci-fi TV series, but when he and his co-stars (including Sigourney Weaver and Alan Rickman) find themselves in outer space on a real spaceship dealing with real aliens, they've got to do it for real… and there are some hiccups at the start. A fun adventure and humorous homage to the genre and show business, Galaxy Quest is darn-near perfect.
5. Clueless
Year: 1995
Director: Amy Heckerling
"As if!" A loose adaptation of Jane Austen's novel Emma, Clueless is one of the great '90s comedies and valley girl movies. Clueless stars Alicia Silverstone as Cher Horowitz, a popular girl at a Beverly Hills high school who decides she wants to better herself. A parade of incredible fashions, iconic lines, and gentle satire of materialism, the classic comedy captures a slice of the decade better than just about any other movie could hope to. It's also great to watch if you want to see how Paul Rudd basically looks the same in this movie as he does 30 years later. It's like he doesn't age!
4. Groundhog Day
Year: 1993
Director: Harold Ramis
Bill Murray stars as Phil Connors, a weatherman who goes to the Punxsutawney, Pennsylvania to cover the town's Groundhog Day festivities only to wake up the next morning and find that it's somehow still February 2 and he has to live the whole day all over again… and again… and again and again. The ultimate time loop movie gets a lot of praise of its philosophical interpretations, but it's tremendously funny as a straight-up comedy, too, getting a lot of mileage out of Phil's frustration and escalating efforts to escape the loop—or at least cause a little chaos before "I Got You Babe" starts playing once more.
3. Austin Powers: International Man of Mystery
Year: 1997
Director: Jay Roach
One of the funniest and certainly the most shagadelic comedies of the '90s, Austin Powers: International Man of Mystery is a spoof of James Bond movies, starring Mike Myers as the titular spy. A man of the swingin' '60s, Austin is cryogenically frozen so that he can be there to stop his archnemesis, Dr. Evil (also played by Myers), should he ever return. But when he's thawed out in 1997, Austin finds that this decade is very different from the free love era he hailed from. Extremely quotable (ask anybody who was alive when it came out if they have a favorite quote and chances are you'll get a "yeah baby" in response), Austin Powers is a cleverly nostalgic romp—one that's gaining new resonance as the '90s are increasingly as distant as the '60s were to this movie's release.
2. Office Space
Year: 1999
Director: Mike Judge
Ron Livingston stars as Peter Gibbons, a white collar worker who has no passion for his programming job, and after being hypnotized, he simply stops caring or trying to apply himself." To his bemusement, checking out does wonders for his career. When he and his co-worker friends decide to try to get what they think the company owes them, complications ensue. Despite (or perhaps because of) how dry much of its humor is, Office Space is a blisteringly accurate takedown of corporate culture, one that anybody who has worked in an office will be able to laugh at because, well, it's either that or cry.
1. The Big Lebowski
Year: 1998
Directors: Joel and Ethan Coen
The competition is fierce, but The Big Lebowski, Joel and Ethan Coen's crime comedy about a slacker, just might be the brothers' best—and funniest—film. Jeffrey "The Dude" Lebowski (Jeff Bridges) lives an exceedingly chill life in Los Angeles, which he mostly spends bowling and drinking White Russians, until he's assaulted by some goons who mistook him for a millionaire with the same name (the titular "Big" Lebowski). The Dude soon finds himself in the midst of a ransom plot, the complexities of which don't matter because the mystery is just a framework for odd laughs and supreme vibes.
