62 items
A romantic comedy built on a very 2002 premise: a heartbroken San Francisco web designer swears off all sexual contact for the 40 days of Lent — right as he meets the perfect woman. Josh Hartnett at the peak of his heartthrob moment, opposite Shannyn Sossamon.
The SNL goofball who became a box-office machine — Billy Madison, Happy Gilmore, The Wedding Singer, The Waterboy. In the '90s his man-child comedies and shouty voices made him one of the most bankable comedians alive.
The teen comedy that launched a thousand locker-room chants and made 'MILF' a dinner-table word—whether your parents were ready or not. A crew of high schoolers make a pact, and the resulting chaos defined the 2000s comedy formula. You either rented this VHS or pretended you didn't watch it on cable.
"Stay classy, San Diego." Will Ferrell's mustachioed 1970s news anchor Ron Burgundy and his idiot news team gave the 2000s an endlessly quotable comedy — "I love lamp," "60% of the time, it works every time."
The manic variety cartoon that slipped jokes for adults past kids and a geography lesson past everyone. Yakko, Wakko and Dot burst out of the Warner Bros. water tower alongside Pinky and the Brain, Slappy Squirrel, and a cast of oddballs — fast, smart, and endlessly quotable.
![Video thumbnail — Beavis and Butthead Do America (1996) Theatrical Trailer [4K] [5.1] [FTD-1015]](https://i.ytimg.com/vi/RzYWKWtRmzQ/maxresdefault.jpg)
MTV's cackling couch potatoes trade their couch for a cross-country road trip when their TV gets stolen. It's chaotic, it's vulgar, and it opened #1 with the biggest December weekend any film had ever managed at the time. Mike Judge's feature debut turned a controversial TV phenomenon into a theatrical event that felt impossibly big.
An international drinking competition disguised as a sports movie. Two brothers spread their grandfather's ashes at Oktoberfest and accidentally stumble into Beerfest—a secret underground tournament where nations compete in beer games—then return home to assemble an American dream team. Like Super Troopers before it, its cult life was lived on DVD, in dorm rooms and at beer-soaked parties.
Martin Lawrence as an FBI agent who goes undercover as a gun-toting Southern grandmother, prosthetics and fat suit and all. Critics groaned, but the one-joke premise turned into a $170-million summer smash and launched a franchise.
The 2001 Martin Lawrence comedy where a modern theme-park worker falls in a moat and wakes up in medieval England, fish-out-of-water antics ensuing. A critical flop that a whole generation still somehow watched on cable a dozen times.
An 11-year-old writes a blank check for a million dollars and actually cashes it—a premise every kid dreamed of but only this movie let them live out. Critics hated it; CinemaScore gave it an A−; and every child of the 90s rented it anyway, because fantasy was the whole point.
Sacha Baron Cohen's mockumentary phenomenon: his clueless Kazakh TV journalist Borat rampages across America interviewing real, unsuspecting people, exposing what they'll say to a "foreigner." Spun off from Da Ali G Show, it was a critical smash, a quoting machine ("Very nice!"), and a diplomatic incident all at once.
The decade's most likable leading man: caveman in Encino Man, gentleman in School Ties, jungle king in George of the Jungle, and finally the revolver-twirling hero of The Mummy. Hollywood's nicest action star — and the comeback story the whole internet rooted for.
One high-school graduation night, one undelivered letter, and four years of bottled feelings ready to spill. Preston Meyers has spent his high-school career invisibly loving Amanda Beckett, and in the chaos of a packed house party, he's got one last shot to tell her before everyone scatters for good. An ensemble of misfits, jocks, goofballs, and dreamers—each chasing their own moment—makes it the whole 90s teen-movie yearbook in one house.
The odd-couple sitcom that dominated Nickelodeon screens in the early 2000s. Drake Bell and Josh Peck as mismatched step-brothers—one cool and laid-back, one neurotic and anxious—got into schemes that escalated from household mishaps to ridiculous chaos, and it was impossible not to laugh along.
The Farrelly brothers' breakout comedy starred Jim Carrey and Jeff Daniels as two hopelessly incompetent best friends on a cross-country road trip. Dumb and Dumber capped Carrey's historically unprecedented 1994—the year he also starred in Ace Ventura and The Mask—and grossed nearly $250 million worldwide on a modest budget.
A profane, darkly funny HBO series about a washed-up baseball pitcher who returns to his hometown with nothing but a mullet and monumental delusions. Created by Danny McBride (who also stars), it turned small-town mediocrity into comedy gold.
Three kids with the same name and one unstoppable goal: scam the neighborhood kids out of quarters for jawbreakers. Ed, Edd n Eddy ran a full decade on Cartoon Network and turned suburban con artistry into an art form.
Elf (2003) is the Christmas comedy directed by Jon Favreau starring Will Ferrell as Buddy, a human raised by elves at the North Pole who travels to New York City to find his real father. Buddy's childlike wonder and confusion about human culture—from his syrup-on-spaghetti diet to iconic lines like "Buddy the Elf, what's your favorite color?"—made it an instant, endlessly-rewatched holiday classic.
One movie star, his three guys from Queens, and the super-agent screaming them all toward the top. Entourage was HBO's mid-2000s fantasy of Hollywood — Maseratis, premieres, Malibu — and Jeremy Piven's Ari Gold turned "let's hug it out" into the decade's boardroom catchphrase. Aspiration as entertainment, and for a few years it absolutely worked.
A post-graduation beer-fueled romp across Europe in search of a German pen pal who turns out to be a girl. The premise is thin and the plot is chaos, but it left behind "Scotty Doesn't Know"—a breakup anthem so infectious it outgrew the movie—and earned itself a permanent slot in the dorm-room DVD rotation.
Flight of the Conchords stars Bret McKenzie and Jemaine Clement as fictionalized versions of themselves—a deadpan New Zealand musical-comedy duo struggling to break into the NYC music scene while writing and performing original songs. Created by James Bobin, Jemaine Clement, and Bret McKenzie, the show aired on HBO from 2007 to 2009 with a small but devoted cult following. Their oddball manager Murray Hewitt (Rhys Darby) and their lone superfan Mel (Kristen Schaal) round out their world. Signature songs like 'Business Time' and 'Hiphopopotamus vs. Rhymenoceros' became instant cult classics.
The washed-up cast of a canceled space show gets abducted by aliens who watched the reruns and thought they were documentaries. "Never give up, never surrender!" The Star Trek parody so good that actual Trek fans voted it one of the best Star Trek films — and it isn't one.
A 36-year-old video-game tester gets evicted and moves in with his grandma and her roommates, where he's surrounded by pajama-wearing grandmothers, a dealer named Dante with a pet chimp, and the crushing weight of being a grown man living with his grandma. Critics absolutely eviscerated it. Then the DVD turned it into a canonical stoner comedy.
Adam Sandler as a failed hockey player with a 400-yard running drive and a grandmother in trouble with the IRS — somehow this became a 1996 classic. Christopher McDonald's smug Shooter McGavin, Carl Weathers' one-handed mentor Chubbs, and a Bob Barker brawl that won MTV's Best Fight. You've attempted the Happy Gilmore swing at least once.
The world's most famous exhibition basketball team didn't come from Harlem and almost never loses. Born on Chicago's South Side in the 1920s, they've spent a century mixing trick-shot artistry with comedy routines in packed arenas—their whistled theme "Sweet Georgia Brown" is as iconic as the alley-oop that made you jump out of your seat.
Two best friends, one impossible late-night craving, and an obstacle course of absurdity standing between them and White Castle sliders. A modest $9 million theatrical release that became a genuine DVD phenomenon — and a quietly groundbreaking one: a mainstream studio comedy carried by two Asian-American leads, at a time when the industry insisted that couldn't work.
Kevin boards the wrong plane and lands in New York with his dad's bag and credit card — cue the Plaza Hotel, the pigeon lady, and traps somehow crueler than the first movie's. The rare sequel kids argued was better than the original.
![Video thumbnail — Home Alone - Official® Trailer [HD]](https://i.ytimg.com/vi/Fmih-zWIjGY/maxresdefault.jpg)
Kevin McCallister is accidentally left behind when his family flies out for the holidays — and when two bumbling burglars invade, the eight-year-old's creative defenses (ice, tar, paint cans, and a very hot doorknob) turn the house into a gauntlet of booby traps. It became the defining Christmas movie of a generation, making Macaulay Culkin the most famous kid on the planet.
Tim Allen's 'Tool Man' ruled the suburban garage with more power and less wisdom than any homeowner should wield. Home Improvement was a blue-collar sitcom about mishaps, masculinity, and the perpetual mystery behind Wilson's always-hidden fence.
The prehistoric buddy comedy that put Blue Sky Studios on the map: a woolly mammoth, a sloth, and a saber-toothed tiger reluctantly team up to return a lost human baby to its tribe, while a nut-obsessed squirrel named Scrat wages an eternal, silent war against a single acorn. A surprise blockbuster that launched one of animation's biggest franchises.
The Playmate who snort-laughed at the glamour game. As MTV's Singled Out co-host she buried the pin-up script under googly faces and gross-out physical comedy — and proved a bombshell could be the funniest person in the room.
The Canadian comic who became the biggest movie star on the planet in a single calendar year. In 1994, Ace Ventura, The Mask, and Dumb and Dumber made Jim Carrey the hyperkinetic face of the decade — rubber-faced, fearless, and everywhere.
A mullet-wearing janitor drifts across America searching for the parents who lost him at the Grand Canyon. Panned by critics but reborn as a cable classic, Joe Dirt proved that weird comedies find their people eventually—they just needed TBS and a Saturday night.
A one-night stand with immediate, life-rearranging consequences. Judd Apatow's follow-up to The 40-Year-Old Virgin crashed slacker comedy into romantic comedy and somehow made you believe both. Seth Rogen graduated from stoner sidekick to leading man in real time, opposite Katherine Heigl as the career-focused woman suddenly sharing a future with him.
Reese Witherspoon as Elle Woods, the pink-clad sorority queen who follows her ex to Harvard Law and out-lawyers everyone. A 2001 sleeper hit that made "bend and snap" a catchphrase and launched a franchise.
A fast-talking lawyer who lies for a living is magically cursed to tell only the truth for 24 hours after his neglected son blows out his birthday candles with a single wish. Peak rubber-faced Jim Carrey, physically at war with his own mouth. Directed by Tom Shadyac, it was one of 1997's biggest comedies.
A shape-shifting comedy force. On Martin he played a Detroit radio DJ—and an entire neighborhood of other characters: Sheneneh, Mama Payne, Jerome, Dragonfly Jones. The show was one of Fox's highest-rated and made him a star; stand-up and movies (Bad Boys, Big Momma's House) carried the run into the 2000s.
The teen comedy that defined 2000s school social hierarchies — cliques, calculation, and the crushing realization that you might be the problem. Mean Girls premiered in April 2004, written by SNL's Tina Fey, and immediately became the movie every middle and high school student quoted obsessively for the next decade.
Robin Williams, four hours in the makeup chair every morning, running through a restaurant quick-change like his life depended on it. The film that proved you could make a comedy about a family falling apart and still have it be genuinely touching—a rare balance the 90s got right, and a comfort object ever since.
A deadpan indie comedy about an awkward teenager in small-town Idaho navigating high school, family chaos, and his own social ineptitude. Released in 2004, the low-budget film became a quotable phenomenon with unforgettable moments — "Gosh!", "Vote for Pedro", tetherball showdowns — and spawned endless merchandise and T-shirt catchphrases.
Robin Williams as the real Dr. Hunter "Patch" Adams — a medical student who prescribes laughter, wears a clown nose on the children's ward, and dreams of a free hospital. Audiences packed theaters and cried; critics savaged it; the real Patch Adams hated it. A defining late-90s Robin Williams memory either way.
Nickelodeon's cult-favorite series about two red-haired brothers, both named Pete, navigating a suburbia that was equal parts mundane and magical. Between the deadpan narration, the indie-rock soundtrack, and Artie, the Strongest Man in the World, it was a kids' show smart enough for adults.
A handheld COPS parody that never broke character. The hapless deputies of a fictional Reno Sheriff's Department stumbled through investigations with the deadpan energy of a mockumentary, mixing inspired improvisation with the comfort of a familiar ensemble—short-shorts, bad judgment, and the weird alchemy of characters who felt like actual people. Six seasons of controlled chaos.
Macaulay Culkin as the richest kid in the world in a mansion with a working McDonald's inside it—a fantasy of 90s excess that hit a little different for a generation of latchkey kids. The film was panned and underperformed at the box office, and yet Richie Rich became a cultural touchstone for a very specific kind of 90s wish fulfillment.
A college kid's one-night mistake gets caught on tape—and the tape gets mailed to his long-distance girlfriend. Cue an 1,800-mile scramble to intercept it, with Tom Green's unhinged campus tour guide narrating the whole saga as local legend. Depraved and stupid exactly as intended, it rode the post-American Pie wave into dorm-room immortality.
Stand-up comic turned Hollywood golden boy whose late-80s-to-90s run defined a generation's movie shelf. From Good Morning, Vietnam (1987) through Good Will Hunting's 1998 Oscar win, Williams embodied the comedic-yet-sensitive everyman that shaped 90s cinema.
Rocko the wallaby and friends stumbled through suburban absurdism in a show that smuggled adult satire past Nickelodeon's censors. Crude, weird, and weirdly brilliant — the launching pad for future SpongeBob creators.
Nickelodeon's 1991 animated series gave the world the Pickles household — a group of talking babies narrating their daily adventures and misadventures with brilliant, absurdist humor. Rugrats proved that cartoons for kids didn't need to be dumbed down; the show's clever writing and wild imagination made it appointment TV for 90s kids and their parents.
The buddy-cop smash that paired Hong Kong action legend Jackie Chan with motormouth comedian Chris Tucker as mismatched cops forced to team up on a kidnapping case in Los Angeles. Chan's stunt-comedy and Tucker's nonstop riffing turned culture-clash friction into one of 1998's biggest hits — and launched a franchise.
A deadpan dog detective in a suit and his "hyperkinetic rabbity thing" partner road-trip across America's tackiest tourist traps chasing an escaped carnival bigfoot. LucasArts' 1993 point-and-click classic was sharp, absurd, and voiced by the actual voice of Disney's Goofy.
The hospital show that could cut from a surreal daydream about a floating head to genuine grief—all in one episode. Scrubs proved that comedies could be funny and devastating, that a laugh track wasn't required when your writing was this sharp, and that TV bromance could hit as hard as any drama.
"A show about nothing" created by Jerry Seinfeld and Larry David became everything. NBC's quirky hit turned observational humor about minutiae—shirt buttons, parking spots, the mechanics of social obligation—into the decade's most quotable comedy.
Jack Black gets hypnotized by Tony Robbins (yes, really, playing himself) to see only inner beauty, and falls for the woman of his dreams—who happens to be wearing a 25-pound fat suit. It's a broad comedy that made a lot of money and aged like milk left in the sun. Modern rewatching is complicated by the fact that the actors who wore that suit lived through genuine hurt.
The grumpy ogre who just wanted to be left alone, dragged into a quest to rescue a princess and discover his own capacity for love. Shrek arrived in May 2001 as a subversive fairy-tale comedy from DreamWorks, won the first Academy Award for Best Animated Feature, and spawned a franchise that defined early-2000s family cinema.
A low-budget indie that became a word-of-mouth empire. Five Vermont state troopers prank their way through a dead stretch of highway—the all-'meow' traffic stop, the maple-syrup chug, Farva's immortal 'liter of cola'—while feuding with the local cops. Theaters shrugged; the DVD made it a generation's comedy bible.
A last-week-of-high-school panic attack disguised as a party movie. Two best friends on a doomed one-night quest to buy alcohol, and a fake ID bearing a single name — McLovin — that instantly became the decade's most famous prop. This was the R-rated teen comedy that felt like watching your own friends instead of a movie.
A Disney Channel hit (2003–2007) starring Raven-Symoné as Raven Baxter, a San Francisco teen who experiences brief psychic visions of the future. The show's running gag: Raven's attempts to change what she's foreseen inevitably cause the very chaos she was trying to prevent. One of the network's biggest comedies of the era, it was among the first Disney Channel sitcoms led by a Black female lead.
A mistaken-identity bowling noir built on White Russians, nihilists, and the definitive 90s character: the Dude, a Los Angeles pot-smoking bowling bum who stumbles into a kidnapping plot. Its theatrical run was modest and critics were lukewarm. Then something strange happened: it became THE cult film of its generation, spawning a religion and a traveling film festival dedicated entirely to its worship.
A straight-arrow high-school senior, a gorgeous new neighbor with a secret past, and the eternal question: "is the juice worth the squeeze?" It underperformed in theaters — then found its real audience on DVD and late-night cable, where it quietly became one of the 2000s' most rewatched teen comedies.
A Canadian comedian and prankster whose MTV show turned everyday chaos into absurdist performance art. Tom Green built a cult following by harassing his own parents on camera, hitting No. 1 on TRL with a song about putting his bum on things, and turning a testicular cancer diagnosis into a shockingly honest TV special. He was unhinged before unhinged was a brand.
Two guys broadcasting a cable-access show from a basement in Aurora, Illinois became a $183 million blockbuster — still the biggest movie ever made from an SNL sketch. "Schwing!", "…NOT!", "We're not worthy!" colonized every hallway in America, and one headbanging scene in an AMC Pacer sent Bohemian Rhapsody back up the charts seventeen years after its release.
The king of musical parody, Alfred Matthew Yankovic turned accordion jokes and lyrical hijinks into a decade-long MTV empire. He made fun of the songs everyone loved—and everyone watched him do it.