The Top 100+ Funniest Movies of All Time

Looking for a laugh? Check our picks for the best cinematic comedies.

slickersThe Funniest Movies of 1990-2000:
CITY SLICKERS (1991) Afflicted by various midlife crises, three urbanites (Billy Crystal, Bruno Kirby, Daniel Stern) try to sort things out on a cattle drive. The complications are unfailingly merry, and Jack Palance–as the rough-hewn, straight-faced head drover–makes John Wayne look like Shirley Temple.

SOAPDISH (1991) Daytime soap operas make an easy target. However, thanks to fine performances by Kevin Kline as an aging ham, and Sally Field as his ex, there’s a lot to think about and laugh at. Whoopi Goldberg, Garry Marshall. Robert Downey, Jr., and Elisabeth Shue add deliciously to the mix.

A LEAGUE OF THEIR OWN (1992) Penny Marshall’s valentine to a women’s hardball league during WWII when male players were in the service. Terrific performances by Geena Davis, Madonna (!), Rosie O’Donnell and Tom Hanks. (“There’s no crying in baseball.”)

MY COUSIN VINNY (1992) Joe Pesci, a Brooklyn loudmouthpiece heads to Wazoo, Alabama, to defend his innocent cousin (Ralph Macchio) in a murder trial. Ba-da-bing farce, with a star turn by Marisa Tomei as Joe’s amusing side-of-da-mouth girlfriend.

GROUNDHOG DAY (1993) Egomaniacal weatherman Bill Murray spends a night in Punxsutawney, Pa., where the local groundhog is supposed to see his shadow and predict how long winter will last. Trouble is, Murray gets caught in a time trap, and keeps repeating the day, minute by minute, day after day. Scrooge becomes saint, but not before some funny and wise interludes, supervised by director Harold Ramis.

FOUR WEDDINGS AND A FUNERAL (1994) Blithe British comedy about a young man (Hugh Grant) who can’t commit until he meets an unattainable woman (Andie MacDowell). With a choice supporting cast, under Mike Newell’s direction.

DUMB AND DUMBER (1994) Jim Carrey and Jeff Daniels bring respect back to the buddy road trip genre by debasing themselves entirely. As kindred morons cut from the same whoopee cushion, Carrey and Daniels embark cross-country for love, become social elites for a weekend, accidentally thwart a kidnapping, and frustrate the bejeesus out of everyone they meet along the way. Wanna hear the most annoying sound in the world? Look no further.

CLERKS (1994) Through black-and-white vignettes set in a New Jersey Quick Stop, director Kevin Smith’s first film captures the funny, the raunchy, the horrible, and occasionally the sublime moments of life at a terrible day job. Most of the comedy wasn’t even a stretch; Smith wrote and shot the film for about $27,000 in the convenience store where he worked, making Clerks the first major cult comedy success of the ‘90s home movie era. Not to brag, but it’s also the most stolen American VHS tape of all time.

ACE VENTURE: PET DETECTIVE (1994) As Miami’s Sherlock Holmes of animal-related crimes, Ace Venture must break up a dolphin-smuggling ring to save the Super Bowl. Don’t knock the script for being unoriginal! Beyond the menagerie of quips and physical comedy set pieces, this outlandish caper transformed character actor James Carrey into the limb-flailing Jim of legend, beginning an era where Carrey could do no wrong—even while, literally, talking out of his behind.

BABE (1995) That rarity of rarities, an authentic family comedy, about an orphaned piglet growing up on a farm in the company of dogs, sheep and people, all of whom can talk–except that only the animals can understand one another. Exceptional animatronic effects.

TOY STORY (1995) One of the most important movies ever made about friendship stars Tim Allen as a plastic space man—and no, we’re not talking about Galaxy Quest. The first of many excellent Disney-Pixar feature film collaborations, Toy Story set a new standard for computer animation, and family-friendly comedy strong enough to crack the hardest polyurethane hearts.

BILLY MADISON (1995) Fresh out of Saturday Night Live, Adam Sandler finds himself back in elementary school to prove he’s mature enough to manage his father’s fortune. Chris Farley, Norm MacDonald, Robert Smigel, and Steve Buscemi help plot the supremely juvenile, perpetually quotable curriculum. Silly voices ensue.

JERRY MAGUIRE (1996) The social commentary never loses its sense of humor in this full-length portrait of a venal sports agent (Tom Cruise) whose client lives by the slogan, “Show me the money.” Adroit backup by Cuba Gooding, Renée Zellweger and some actual athletes.

THE FULL MONTY (1997) Unemployed steelworkers try a new line of work–they become male strippers. Surprisingly sensitive and unfailingly witty presentation of underclass Britain by director Peter Cattaneo. Anne Dudley’s score won an Oscar.

MEN IN BLACK (1997) Alien conspiracy culture takes some good-natured ribbing in this sci-fi farce. Will Smith and Tommy Lee Jones are the titular men sent to save us from space invaders. Fantastic special effects.

AS GOOD AS IT GETS (1997) Jack Nicholson plays an obsessive-compulsive author who can’t get through the day without the help of his favorite waitress, Helen Hunt. Great cast, great lines, and Nicholson meets his match in a tiny little dog, who is as crazy as he is.

AUSTIN POWERS: INTERNATIONAL MAN OF MYSTERY (1997) The trilogy may blur into a randy, psychedelic cocktail of inept espionage and poor dental hygiene, but Mike Myers’ debut performances as Dr. Evil and Austin Danger Powers easily rank as his best roles in the post-Wayne’s World world. Armed with a cameo cast of Will Ferrell, Carrie Fisher, Tom Arnold, Rob Lowe, Christian Slater, and Burt “Frickin’” Bacharach, Powers infiltrates its way into the parody pantheon. Non-believers, we have one word for you: Shhh.

THE BIG LEBOWSKI (1998) After he’s mistaken for a millionaire of the same name, Jeffrey “The Dude” Lebowski and his bowling buddies enter a world of pain. Part Western folk legend, part Buddhism-via-bowling parable, part hard-boiled trip down the rabbit hole to L.A.’s darkest, weirdest crannies, the Coen Brothers’ Big Lebowski is a brilliant, bizarre, and endlessly quotable universe unto itself. The Dude abides—and the world abides with him.

YOU’VE GOT MAIL (1998) An elegant update of The Shop Around the Corner (1940), this time with two competitive bookstore owners sending each other anonymous, hostile e-mails. Tom Hanks and Meg Ryan shine under the direction of Nora Ephron, who is singlehandedly reviving the spirit of classic cinema comedy-romance.

SHAKESPEARE IN LOVE (1998) Writers Tom Stoppard and Marc Norman see the Bard of Avon (Joseph Fiennes) not as a sublime poet/playwright, but simply and amusingly as a writer on deadline, trying to bat out Romeo and Ethel, the Pirate’s Daughter, before the creditors close in. Anachronistic yet effective situations abound, along with some tasty cross-dressing by Gwyneth Paltrow. The amiable cast includes Simon Callow, Geoffrey Rush and Judi Dench.

THERE’S SOMETHING ABOUT MARY (1998) Indeed there is, as played by Cameron Diaz, and Ben Stiller has craved it since high school. Now that she’s a lady every other man does, too. Sophomoric? Yes. Hilarious? Absolutely. Matt Dillon helps.

AMERICAN PIE (1999) Familiar story of young men trying to lose their virginity and being thwarted at every turn. Unlike earlier teenflicks, however, this farce doesn’t put down grownups, and gives some of its best lines to female characters. Ultimately, however, what gives this Pie its tart sweetness is an endearing cast, led by Jason Biggs, Eugene Levy and Alyson Hannigan.

OFFICE SPACE (1999) Mike Judge offers the most hysterical movie to ever feature the word “TPS report” in this painfully accurate satire of white-collar woe. We’ve all known droning bosses and pathetically stapler-obsessed cubicle-mates—but a set piece where three disgruntled office heroes beat the crap out of an uncooperative desktop printer is a reward that’s even worth coming in on a Sunday for.

ANALYZE THIS (1999) A mob capo (Robert De Niro) suddenly begins to suffer from panic attacks. Distressed, his bodyguard (Joe Viterelli) seeks out a shrink (Billy Crystal). and the complications begin. The doctor is a family psychiatrist, but this is definitely not the kind of family he had in mind. De Niro displays a great gift for comedy, and a very funny Crystal doesn’t make the obvious choices. Even so, Viterelli practically steals this surprisingly well-made picture.

TOPSY-TURVY (1999) Backstage lives of those 19th-century masters of operetta, W. S. Gilbert and Arthur Sullivan. Richly detailed direction by Mike Leigh, with persuasive performances by Jim Broadbent, Allan Corduner and supporting players.

NEXT: 1980-1990

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