22 items
A witty modernization of Shakespeare's The Taming of the Shrew transplanted to a Seattle-area high school, starring Julia Stiles and Heath Ledger. A modest hit in theaters, it grew into a generational classic and launched the breakout careers of its three young leads.
![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 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.
The everyman action hero who proved you didn't need muscles the size of tree trunks to save the day. Bruce Willis went from TV comedy to Die Hard's John McClane, rewriting what a blockbuster lead could be—and spent the next decade proving it with an eclectic run of '90s classics that kept him in the conversation.
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.
A sharp, seductive update of Laclos' 1782 novel Les Liaisons dangereuses transplanted to Manhattan's prep-school elite, starring Sarah Michelle Gellar and Ryan Phillippe. Written and directed by Roger Kumble, it became a defining late-90s teen drama with genuine cultural impact.
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.
Left at a ranch while their family is away — and convinced they've been abandoned — two dogs and a cat set out across the wilderness to get home. Chance, the reckless young American Bulldog; Sassy, the imperious Himalayan cat; and Shadow, the wise old Golden Retriever, against the Sierras. Disney's remake of its own 1963 classic earns every tear it takes from you.
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.
The hands-on-cheeks scream that launched a thousand parodies. As Kevin McCallister in Home Alone, Culkin became the most famous child star on Earth — and, briefly, the highest-paid kid in Hollywood.
A classically trained dancer from Canada who became the scream queen of the '90s. Party of Five made her a household name; The Craft proved she could anchor a cult phenomenon. By Scream 3, Sidney Prescott was her definitive role—the rare horror heroine who could carry an entire franchise. In the 2000s, she stepped back to pursue her own creative vision.
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.
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.
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.
From the daytime soap to teen idol, Ryan Phillippe was the smirking heartthrob who could play both the innocent and the seducer. I Know What You Did Last Summer introduced him; Cruel Intentions cemented him as the defining rich, dangerous charmer of his moment. He married Reese Witherspoon in 1999 and became one of the era's most visible celebrity couples before their 2006 separation.
A modern Pygmalion: class president bets he can turn an art-nerd girl into prom queen in six weeks. Released January 29, 1999, directed by Robert Iscove, it became the surprise smash that crowned the entire late-90s teen-movie wave. A staircase reveal, a perfect song, and one of the era's most-rewatched moments.
![Video thumbnail — STARSHIP TROOPERS [1997]– Official Trailer (HD)](https://i.ytimg.com/vi/zPYuV_jGk7M/maxresdefault.jpg)
Paul Verhoeven's militaristic sci-fi satire based on Robert A. Heinlein's 1959 novel, starring Casper Van Dien as a young soldier fighting giant bugs in a fascistic future society. A visual spectacle that was widely misunderstood upon release but has become a celebrated cult classic.
The film that taught you to roar and made you cry at a father's death—all before your tenth birthday. Disney's juggernaut — Hamlet with lions — dominated the box office and pop culture like nothing before it, a phenomenon that didn't fade with the VHS but exploded into merchandise, video games, and eventually Broadway's best-grossing production ever.
Jim Carrey's first great dramatic turn: Truman Burbank is an ordinary insurance salesman who slowly realizes his entire hometown is a giant TV set and everyone he knows is an actor — his whole life broadcast 24/7 to the world. Directed by Peter Weir from an Andrew Niccol script, it turned a high-concept nightmare into a tender, unsettling fable that only looked more prophetic as reality TV took over.
![Video thumbnail — Rookie of the Year (1993) Theatrical Trailer [4K] [FTD-1393]](https://i.ytimg.com/vi/gUAoirkeaVE/maxresdefault.jpg)
Las Vegas native who became the face of two defining family-movie fantasies—and then grew up into American Pie. From Rookie of the Year's 100-mph kid pitcher to King Arthur's time-traveling Calvin to Kevin in the American Pie gang, his roles bookend an entire decade of growing up.
Two storm-chasing exes and an experimental sensor pod named Dorothy, racing a corporate rival — and the sky itself — across the Plains. It gave the world a CGI flying cow, "We got cows," a near-$500 million gross, and, quietly, one of the first movies ever released on DVD in America.
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.