27 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 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.
A tech-industry thriller starring Ryan Phillippe as a young programmer recruited by a charming but sinister software CEO (Tim Robbins) who steals code and eliminates threats. Released with Microsoft's real antitrust battle still in the headlines, it became a cult artifact of the dot-com era despite critical and commercial failure.
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.
Tim Burton's warmest film: a dying father who has always told his life as a series of tall tales — a giant, a witch who shows your death in her eye, a perfect hidden town called Spectre — and the grown son trying to sort truth from myth before it's too late. Ewan McGregor plays the young father in the fables, Albert Finney the old man telling them.
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.
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.
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.
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.
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.
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 church-family daughter from 7th Heaven who shed her wholesome image and fought her way into 2000s movie stardom. Cast at fourteen as Mary Camden, she became one of The WB's defining faces—and by her early twenties she was headlining studio films like The Texas Chainsaw Massacre and Blade: Trinity.
Denzel Washington as a working father who takes an emergency room hostage when his insurance won't cover his young son's life-saving heart transplant. A blunt, angry drama that critics panned and audiences turned into a hit — and that landed as a lightning rod in America's healthcare debate.
A Minnesota kid who exploded into stardom in 2001 with Pearl Harbor and Black Hawk Down, then famously stepped away. Josh Hartnett was the rare leading man who'd had enough of the machinery by 2006, turning down Superman and Batman to reclaim his life. His withdrawal was deliberate—a quiet rejection of what the moment demanded.
Born 1981, she was the teen-Shakespeare queen of the late 90s and early 2000s—flinty and wry where others were bubbly, older-souled than the wave around her. From Kat Stratford's taming to Ophelia to Desdemona to a ballerina's breakthrough, she was the thinking kid's teen-movie star.
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.
Tim Blake Nelson's modern Othello, relocated to an elite Southern prep school where basketball replaces Venice's wars. Mekhi Phifer as the only Black student and star athlete, Josh Hartnett as the jealous rival, Julia Stiles as Desdemona. It was made to be released in 1999—but held from the world for two years after Columbine.
The teenager with a critic's favorite first kiss who grew into the 2000s' defining star. Southern charm and comic precision built through the '90s—Fear, Freeway, Election—but then Legally Blonde detonated, and she owned the decade. Walk the Line proved she could do Oscar-worthy dramatic work. Married and divorced Ryan Phillippe in a trajectory as public as her career was inescapable.
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.
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.
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.
Alexandre Dumas' revenge classic played gloriously straight: betrayal, a hidden fortune, sword fights, and vengeance served exquisitely cold. A January sleeper in 2002 that grew into dad-canon — the cable movie you'd catch on a Sunday afternoon and watch to the end, every single time.
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.
Roger Avary's savage adaptation of Bret Easton Ellis's novel, following three self-destructive Camden College students through a haze of parties, drugs, and cross-wired desire. James Van Der Beek torched his wholesome Dawson's Creek image as the dealer Sean Bateman — younger brother, in Ellis's world, of American Psycho's Patrick Bateman. A box-office flop that became a cult object.
Wolfgang Petersen's big-budget take on Homer's Iliad, with Brad Pitt as the near-invincible warrior Achilles and Eric Bana as the doomed Trojan prince Hector. Gods and all, the myth was stripped down to human politics and combat — a sword-and-sandal epic that was a modest performer at home but a giant hit overseas.
A K2 rescue thriller where the only way up is with nitroglycerin. Chris O'Donnell carries explosives up a frozen mountain while Bill Paxton schemes below, and it's all kicked off by an opening scene in Monument Valley that burns itself into your brain: a father orders his son to cut the rope. It's December 2000 popcorn cinema in its most visceral form.