1. Will Smith
The multi-talented Will Smith came to us on The Fresh Prince of Bel-Air by way of his musical duo, DJ Jazzy Jeff & the Fresh Prince. A goofball with a heart of gold, Smith went on to star in a slew of 90s flicks (Six Degrees of Separation, Bad Boys, Independence Day, Men in Black, Enemy of the State, and Wild Wild West), as well as keeping Bel-Air on the air for six years. Fresh Prince fact: Smith turned down the leading role in The Matrix. Oh well, he already has more money than God anyway. What’s one more blockbuster?
2. Tom Cruise
Tom Cruise kicked off the 90s with the movie Days of Thunder, an unofficial–and terrible–revamping of his 1986 Top Gun role with race cars instead of fighter jets. His choice in performances improved as the decade went on, however, with roles in Interview with the Vampire, the Mission: Impossible franchise, Jerry Maguire, Eyes Wide Shut, and Magnolia.
3. Brad Pitt
What wasn’t Brad Pitt in during the 90s? Pitt had roles in memorable flicks such as Thelma & Lousie, A River Runs Through It, True Romance, Interview with the Vampire, Legends of the Fall, Seven, 12 Monkeys, Sleepers, Meet Joe Black, and, capping off his 90s tenure, the lead role in the movie adaptation Chuck Palahniuk’s infamous novel Fight Club.
4. Jared Leto
If you were a heterosexual teenage girl in the 90s, you most certainly had a fantasy or two about Jordan Catalano, Leto’s role on MTV’s My So-Called Life. His career had a little more oomph than being a teen heartthrob, though, with roles in a number of 90s movies: How to Make an American Quilt, The Last of the High Kings, Prefontaine, The Thin Red Line, Fight Club, and the regrettable horror flick Urban Legend, among others.
5. Freddie Prinze, Jr.
Though he had some minor acting roles prior, the I Know What You Did Last Summer thriller franchise is what really launched his acting career in the late 90s. He went on to play the male lead in 1999’s She’s All That, a tried-and-true teen story of the ugly duckling taking off her glasses to reveal that she was hot all along.
6. Joshua Jackson
Joshua Jackson is best known to 90s kids for his roles of Charlie in The Mighty Ducks, and as Pacey in the pseudo-groundbreaking teen drama Dawson’s Creek, where he appeared in various softcore make-out scenes with young women way out of his league. He also had roles in several movies, most notably Cruel Intentions.
7. Keanu Reeves
Keanu Reeves spent the 90s era of his career trying to live down his Bill & Ted-borne derpiness. In 1994’s Speed, he solidified his place in the limelight. Throughout the rest of the decade, he made a name for himself in a handful of non-comedic movies that were largely flops until he landed the leading role in the sci-fi epic The Matrix.
8 & 9. Matt Damon & Ben Affleck
Good Will Hunting writers Matt Damon & Ben Affleck launched their careers like a rocket with the 1997 film, in which both actors played characters. The film was a critical and commercial success, placing these two squarely in the spotlight and poised to become two of the most successful actors to begin their careers in the 90s.
10. Ben Stiller
Ben Stiller is probably best known to 90s kids for writing, directing and acting in the coming-of-age film Reality Bites. Throughout the decade, he took part in a number of other successful movies: Heavyweights, Happy Gilmore, Flirting with Disaster, The Cable Guy, and There’s Something About Mary, the comedy that broke the most hairstyling barriers since Hairspray.
11. Johnny Depp
Johnny Depp was already a maturing heartthrob by the time the 90s rolled around, but no one could argue that he was still sexy. To boot, he had roles in some pretty infamous films of the decade: Edward Scissorhands, What’s Eating Gilbert Grape and Fear and Loathing in Las Vegas being the major highlights.
12. Bruce Willis
The 90s were filled with epic blockbusters, and it seemed like Bruce Willis was in most of them. Pulp Fiction, 12 Monkeys, The Fifth Element, Armageddon, and The Sixth Sense. There were a few flops in there, too, but Willis probably financed all of his future great great great great great great grandchildren’s college funds with Die Hard sequels alone.
13. Arnold Schwarzenegger
Austrian action star-turned-politician Arnold Schwarzenegger spent the 90s busy, with nearly 11 roles in a ten-year span. Highlights were the 1990’s awkward Kindergarten Cop, True Lies, and the most painful Christmas movie to not star Tim Allen, Jingle All the Way.
14. Brendan Fraser
Encino Man. ‘Nuff said.
15. Robert Downey, Jr.
Robert Downey, Jr. may have had a few good moments in the 90s (specifically with portrayal of Charlie Chaplin in 1992’s Chaplin), but he made the most headlines because of drug use. Or drug possession. Or failure to appear for a drug test.
16. Leonardo DiCaprio
The holy grail of 90s heartthrobs, Leo was wholly inescapable. From What’s Eating Gilbert Grape to The Basketball Diaries to Titanic, DiCaprio starred in over a dozen films from 1991-98.
17. Jonathan Taylor Thomas
Nobody is arguing that Jonathan Taylor Thomas’s career was a legendary one, but it was definitely difficult to avoid his all-too-charming smile during the 90s. His most memorable appearance was a recurring role on the television series Home Improvement, but he lent his voice to the character of Simba in The Lion King, a movie that makes most 90s kids roar with nostalgia.
18. Jackie Chan
Jackie Chan’s career may have began in the 80s, but he solidified his American audience in the 1990s with comedy/action films like Rumble in the Bronx and Rush Hour.
The RuPaul Show may have had a 100-episode run, but the nation’s most iconic drag queen kept also himself busy throughout the 90s by guest starring on shows such as Sister, Sister and Hercules, among others.
20. Hank Azaria
Besides voicing damn near every non-Simpson character on The Simpsons, Hank Azaria was the quintessential sitcom guest star of the decade. He played Phoebe’s scientist boyfriend on Friends, the dog walker on Mad About You, and even a one-episode role on The Fresh Prince of Bel-Air as a cop.
The Fresh Prince of Bel-Air
My So-Called Life