I Ranked 20 Of The ’90s' Biggest Movie Stars By How Their Careers Turned Out
I Ranked 20 Of The ’90s' Biggest Movie Stars By How Their Careers Turned Out
Mike SpohrWed, August 26, 2026 at 12:31 AM UTC
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I was a 14-year-old kid at the start of the ’90s and a wizened old 24-year-old by the end, so the ’90s were definitely my decade. Back then — in those pre-internet days — my friends and I would scour Movieline and Entertainment Weekly for news about upcoming movies, and especially for anything we could learn about the biggest stars under 30. They were close enough in age to relate to — and, yes, crush on — but still older, cooler, and impossibly glamorous to us. And if there was a photo of Winona Ryder with a new haircut, I may or may not have cut it out and taped it to my binder at school. (Massively uncool in retrospect, lol.)
Ron Galella, Ltd. / Ron Galella Collection via Getty ImagesIf you’d asked me back then, I'd have told you that all the young '90s stars on this list were destined for massive careers, but that didn’t turn out to be true for all of them. So today I'm ranking them based on how their careers actually turned out, looking back from the perspective of a now 50-year-old in 2026. (Shit, where did all the time go?)Anyway, here are the 20 biggest stars under 30 from the '90s, according to moi.OK, here we go, counting down from least realized potential to the most:20. Alicia Silverstone
Archive Photos / Getty ImagesWHAT ACTUALLY HAPPENED AFTER 2000: Silverstone was the subject of vicious tabloid body-shaming in the '90s, which she said left her disillusioned with Hollywood. Maybe that played a role in her underwhelming career. While she co-starred in higher-profile movies like Scooby-Doo 2: Monsters Unleashed and Diary of a Wimpy Kid: The Long Haul, they weren't exactly prestige films, and she hasn't been the lead of a major movie this century. Still, it's not all bad news: she endeared herself to Gen Z in Netflix’s The Baby-Sitters Club, delivered a memorably strange supporting performance in The Killing of a Sacred Deer, and was in last year's Best Picture nominee Bugonia. She's a mother and animal-rights activist too. But let’s be honest: when you saw Clueless in 1995, you did not imagine Cher Horowitz would forever remain the high-water mark of her movie career.
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19. Macaulay Culkin
Vinnie Zuffante / Getty ImagesWHAT ACTUALLY HAPPENED AFTER 2000: Well, at first he basically stopped acting after years of working almost constantly as a kid. When he did do something, it was deliberately quirky and almost designed to keep a low profile: the cult favorite Party Monster, voice work on Robot Chicken, and even a comedy-rock band called the Pizza Underground that, no joke, did Velvet Underground covers with the lyrics changed to be about pizza ("Walk on the Wild Side" became "Take a Bite of the Wild Slice"). More recently he had a well-received turn on American Horror Story: Double Feature, and even received a star on the Hollywood Walk of Fame in 2023. Did Culkin fulfill his potential? As an adult movie star, obviously not. But this is a weird one to judge, because it feels like Culkin did exactly what he wanted to do.
Amy Sussman / Getty Images18. Uma Thurman
Rolf Konow / Getty ImagesWHAT ACTUALLY HAPPENED AFTER 2000: Thurman reunited with Tarantino for Kill Bill: Volume 1 and Volume 2 and gave what is probably the defining performance of her career as the Bride. But things got surprisingly uneven after that, with movies like Be Cool, Prime, My Super Ex-Girlfriend, The Producers, and The Accidental Husband. Soon high-profile lead roles dried up, although she has continued working steadily, including playing a sword-wielding villain opposite Charlize Theron in 2025’s The Old Guard 2. She’s also had success on TV, earning an Emmy nomination for her part in NBC’s Smash and appearing on Dexter: Resurrection. In the end, though, it does feel a bit like unrealized potential. To me, the actor capable of knocking Mia Wallace and the Bride out of the park deserved more great roles than she got.
Frazer Harrison / Getty Images for Epic Games17. Gwyneth Paltrow
Steve Granitz / WireImageWHAT ACTUALLY HAPPENED AFTER 2000: Paltrow has remained an ever-present celebrity largely thanks to her wellness and lifestyle Goop brand, even as it drew criticism over some of its health claims. But if we’re looking strictly at her acting career, it certainly fell well below the promise of the ’90s. The 2000s started well enough with her near-iconic performance in The Royal Tenenbaums, but her next film, Shallow Hal, looks incredibly uncomfortable 25 years later. Paltrow played an overweight woman in a fat suit, and the movie was full of cruel jokes about her character's body. From then on she starred in a number of box office underperformers, and she was extremely fortunate to land the role of Pepper Potts in the Marvel universe, as it kept her connected to high-profile movies. Kudos to her, though, for 2025’s hit Marty Supreme, which reminded people that she could still be a compelling screen presence.
Stephane Cardinale - Corbis / Corbis via Getty Images16. Winona Ryder
Ron Galella, Ltd. / Ron Galella Collection via Getty ImagesWHAT ACTUALLY HAPPENED AFTER 2000: Ah, Winona Ryder, my teenage crush. What a weird and wild quarter-century it’s been. Almost immediately, her career hit its lowest point after she was arrested for shoplifting in 2001. The subsequent trial only hurt her reputation more, and Ryder largely stepped away from acting for a while. When you look at her career after that, things were pretty quiet until she began popping up again in higher-profile projects like Star Trek and the acclaimed Black Swan. But the real resurrection came with Stranger Things. As Joyce Byers, Ryder endeared herself to an entirely new generation of fans — many of whom probably had no idea who she was before she landed in the fictional town of Hawkins. It’s been a great comeback, but considering how enormous her promise once seemed, there’s still a sense that we lost a lot of prime Winona years in the middle.
Kevin Winter / Getty Images15. Julia Roberts
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WHAT ACTUALLY HAPPENED AFTER 2000: Things got off to a hot start with 2000’s Erin Brockovich, for which she won Best Actress at the Academy Awards, but really, that was the high-water mark of her career, and this century has been pretty underwhelming. Yes, she was part of the Ocean’s franchise, but she’s really only had two bona fide Julia Roberts Movie™ hits: Eat Pray Love and Ticket to Paradise, which once again teamed her with George Clooney. So what happened? I think part of it is that she sought out more dramatic, prestige parts instead of the kinds of movies that made her famous — namely, romantic comedies. She also took more time away from the screen as the years rolled by to focus on her family and other pursuits. Still, unevenness aside, she absolutely became the Hollywood royalty everyone expected her to be.
Pascal Le Segretain / Getty Images14. Drew Barrymore
Vinnie Zuffante / Getty ImagesWHAT ACTUALLY HAPPENED AFTER 2000: Drew's career this century has been pretty great, but she might take the prize for the most unpredictable career path. Things started very '90s Drew in the '00s, with Charlie's Angels which allowed her to showcase her comedy chops and sex appeal. (Something young people will not believe about Drew Barrymore is that in the '90s she was known as a rebellious sex symbol, famous for flashing her breasts on The Late Show with David Letterman and starring in the erotic thriller Poison Ivy.) But as Drew aged, it seemed she really wanted to make romantic comedies, and she starred in a bunch of successful ones, like Music and Lyrics and 50 First Dates with old friend Adam Sandler. And then, around the end of the 2010s, she seemed to lose interest in acting...so she became a successful talk show host! So, yeah, potential realized, but in a way absolutely no one would've seen coming.
Taylor Hill / FilmMagic13. Cameron Diaz
Vinnie Zuffante / Getty ImagesWHAT ACTUALLY HAPPENED AFTER 2000: Diaz's run continued in a big way. She starred in Charlie’s Angels, played Princess Fiona throughout the enormously successful Shrek franchise, worked with Martin Scorsese in Gangs of New York, made the perennial Christmas favorite The Holiday, and scored hits with What Happens in Vegas, Bad Teacher, and others. At her peak, she was one of the highest-paid women in Hollywood. Then, after 2014's Annie, Diaz stepped away from acting to devote her attention to her family and other businesses. After roughly a decade away, Jamie Foxx helped lure her back for Netflix's 2025 action comedy Back in Action. Credits may be light the last decade or so, but Diaz absolutely became the giant movie star the ’90s promised.
Sebastian Reuter / Getty Images for Netflix12. Johnny Depp
Pool ARNAL/GARCIA/PICOT / Gamma-Rapho via Getty ImagesWHAT ACTUALLY HAPPENED AFTER 2000: With all of his personal drama, it’s easy to forget that Depp had one of the most epically successful careers of the 21st century. He was the star of all five Pirates of the Caribbean movies, which grossed more than $4.5 billion worldwide, and his performance as Jack Sparrow was so iconic that he was actually nominated for Best Actor at the Academy Awards for the first one — something nobody could have predicted about a popcorn movie based on a Disney ride. Two more Best Actor nominations followed, for Finding Neverland and Sweeney Todd: The Demon Barber of Fleet Street. He also leaned hard into his eccentricity in major hits like Charlie and the Chocolate Factory and Alice in Wonderland, making him one of the most idiosyncratic movie stars of all time. Still, the last decade has been pretty weak compared with what came before, although there is now talk that he could return to the Pirates franchise.
Tim P. Whitby / Getty Images for The Red Sea International Film Festival11. Matt Damon
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WHAT ACTUALLY HAPPENED AFTER 2000: It's not always flashy, but Damon's resume this century is very impressive. He's like the Tortoise from the fable The Tortoise and the Hare — slow and steady, methodically appearing in box office hits and critics' favorites year after year without calling much attention to it. Stuff like The Bourne and Ocean's franchises, The Departed, The Martian, and this year's smash The Odyssey. One surprising element of his 21st century career? He never followed up on his promise as a screenwriter. He and Ben Affleck won Best Original Screenplay at the Academy Awards for 1997's Good Will Hunting (a screenplay still used in many film schools to teach writing), but since then he only has three shared writing credits for films that came nowhere near the standard set by Good Will Hunting. Still, he definitely has realized his potential as a great star.
Roy Rochlin / Getty Images for Netflix10. Ben Affleck
Hulton Archive / Getty ImagesWHAT ACTUALLY HAPPENED AFTER 2000: Ben Affleck became a star in the ’90s, but let’s be real: back then, most people would have bet that Matt Damon would eventually far outpace his childhood friend. That’s not really what happened. In the 21st century, Affleck remained a major blockbuster star, headlining Pearl Harbor and becoming Batman in Batman v Superman and Justice League, even if Damon arguably had him beat when it came to acting prestige. But here’s where it gets interesting: while Damon never became the notable writer-director many people expected, Affleck ended up proving that his filmmaking promise was very real, showing a remarkably assured hand behind the camera. He directed acclaimed movies like Gone Baby Gone, The Town, and Argo — with Argo even winning Best Picture!
Andy Wenstrand / SXSW Conference & Festivals via Getty Images9. Angelina Jolie
Jim Smeal / Ron Galella Collection via Getty ImagesWHAT ACTUALLY HAPPENED AFTER 2000: Angelina Jolie had a very busy 21st century — and yes, that included fully realizing her potential as a major star. She started a family of six children, but somehow also found time to launch an idiosyncratic directing career that, while not always completely successful, included the hit Unbroken and interesting projects like In the Land of Blood and Honey and the acclaimed Cambodian drama First They Killed My Father. And then, of course, Jolie was one of only a handful of women in Hollywood who could get a movie made largely on the strength of her name alone. The Lara Croft movies, Mr. & Mrs. Smith, Salt, and the Maleficent films are just a few examples, while her performance in Clint Eastwood’s Changeling earned her an Academy Award nomination for Best Actress. In addition to all that, she did advocacy for refugees and other humanitarian causes.
Vittorio Zunino Celotto / Getty Images8. Natalie Portman
Michael Crabtree - PA Images / PA Images via Getty ImagesWHAT ACTUALLY HAPPENED AFTER 2000: It’s a little surprising looking back at Natalie Portman’s ’90s filmography, because she actually wasn’t in as many defining movies as memory suggests. Léon: The Professional made an impression, Beautiful Girls became a cult favorite, and Star Wars: Episode I — The Phantom Menace was obviously massive. But that was basically it. In any event, she definitely realized her potential post Y2K. Garden State was a hit, even if her character helped usher in the much-maligned “manic pixie dream girl” era, and Portman transitioned smoothly into serious adult roles. She won Best Actress for Black Swan, earned additional Oscar nominations for Closer and Jackie, and even became part of the MCU as Jane Foster. So, yes: a very successful career. Maybe not one defined by nonstop blockbusters, but absolutely one that fulfilled the promise everyone saw early on.
Dia Dipasupil / Getty Images7. Keanu Reeves
Ron Galella / Ron Galella Collection via Getty ImagesWHAT ACTUALLY HAPPENED AFTER 2000: If in the year 2000 you had to predict a male actor on this list who would be irrelevant in 2026, a whole lot of people would have picked Keanu. But they'd have been wrong. Keanu's rep as a bad actor had more to do with his "Whoa, dude!" voice than his talent, and as he aged his voice added a gravitas that wasn't there before. To be fair, he has made a lot of forgettable movies and things slowed considerably after the hit romantic drama The Lake House with his old Speed co-star Sandra Bullock in 2006. But right when people might've been ready to count him out, along came the John Wick franchise. And while this post isn't about whether these stars are good people or not, I'm giving him a few extra points for reportedly being one hell of a dude.
Craig Barritt / Variety via Getty Images6. Will Smith
Getty ImagesWHAT ACTUALLY HAPPENED AFTER 2000: Look, "the slap" was weird AF, and his reputation has definitely taken a big hit (especially since, before this cringefest, he was famous for his charm, charisma, and cool). But let’s not forget that "the slap" happened on the very night he won the Oscar for King Richard. If not for what happened, Smith might've ended up in the number one spot on this list. His movies — like Hancock, The Pursuit of Happyness, and sequels to Bad Boys and Men in Black — were events, and he has more than a dozen movies this century that grossed $250 million or more! Action, comedy, drama, petty slaps...he can do it all.
Jacopo Raule / Getty Images
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5. Reese Witherspoon
Steve.Granitz/ WireImageWHAT ACTUALLY HAPPENED AFTER 2000: As good as Witherspoon was, with the exception of Cruel Intentions, very few of her most memorable ’90s films — like Election and Pleasantville — made much of a dent at the box office. So it was a little surprising just how massive a movie star she became in the 21st century. Obviously, Legally Blonde was huge, but Witherspoon followed it with major hits like Sweet Home Alabama, Four Christmases, and Water for Elephants. She more than fulfilled the acting promise she showed in movies like Election, too. Witherspoon won Best Actress for Walk the Line and earned another Oscar nomination for Wild. She then successfully moved into television with the hits Big Little Lies (which she won an Emmy for) and The Morning Show. You really can’t do much better than that.
Eric Charbonneau / Apple TV via Getty Images4. Kate Winslet
Jim Smeal / Ron Galella Collection via Getty ImagesWHAT ACTUALLY HAPPENED AFTER 2000: It was clear to anyone who saw Heavenly Creatures, Titanic, or even a lesser-known ’90s film like the heartbreaking Jude that Winslet was an actor of the highest caliber. She seemed destined to grow into the kind of grand old dame of acting embodied by legendary British performers like Judi Dench. But even then, I’m not sure anyone could have predicted just how great her career would become. Winslet has earned seven Academy Award nominations, winning Best Actress for The Reader, and moved successfully into television, starring in the wildly acclaimed Mare of Easttown after already winning praise for the miniseries Mildred Pierce. And heck, she even found her way into James Cameron’s Avatar franchise and is now joining The Lord of the Rings universe with The Hunt for Gollum. At this point, saying she fulfilled her potential feels like an understatement.
Dave Benett / Dave Benett/WireImage3. Leonardo DiCaprio
Rose Hartman / Getty ImagesWHAT ACTUALLY HAPPENED AFTER 2000: DiCaprio definitely had that big career, but in some ways he might have come into his own the most in the last decade. He was always a serious actor — our generation's De Niro or Brando — but he looked like he was a sophomore in high school. And while that played to his advantage in something like Spielberg's Catch Me If You Can (where he played a teenager), it tainted his otherwise awesome performance as Howard Hughes in The Aviator because no one was buying him in the third act as a 40-something Hughes. Ditto for J. Edgar (where he played Hoover as a 70-year-old). His baby face never stopped legendary directors from casting him or from racking up the hits. But somewhere around 2015 he started to look convincingly like an adult, and we got some of his best work ever: The Revenant (for which he finally got his Oscar), Once Upon a Time in Hollywood, and One Battle After Another.
Mike Coppola / Getty Images2. Brad Pitt
Getty ImagesWHAT ACTUALLY HAPPENED AFTER 2000: When putting aside the issues in his personal life and focusing on his work, there is no denying he has made what he did in the ’90s look like an amuse-bouche compared with what he’s done over the last quarter century. He’s not only won two Academy Awards, one as an actor for his unforgettable role as Cliff Booth in Once Upon a Time in Hollywood and another for producing 12 Years a Slave, but he’s produced and/or starred in two Best Picture winners, The Departed and 12 Years a Slave, as well as a long list of other Best Picture nominees, including Inglourious Basterds, Moneyball, The Big Short, Once Upon a Time in Hollywood, and F1. There have been lots of blockbusters too, like F1, which grossed $631.5 million, and World War Z, which racked up $540.4 million. He’s arguably THE male movie star of the century.
Gareth Cattermole / Gareth Cattermole/Getty Images for Warner Bros. Pictures1. Sandra Bullock
Vinnie Zuffante / Getty ImagesWHAT ACTUALLY HAPPENED AFTER 2000: Bullock got WAY more successful in almost every way an actor could. Critical acclaim? You bet, she won an Oscar for The Blind Side and was nominated for Gravity. Box office success? Oh yeah, her numerous post-2000 hits (like The Proposal and The Heat) regularly dwarfed her '90s hits (except Speed). Range? Absolutely — she did romance, comedy, serious drama, action, even horror! Look, when it struck midnight on January 1, 2000, I think we all knew Leo would win an Oscar one day. We all knew Julia Roberts would end up Hollywood royalty. But how many of us would have predicted that Sandra Bullock would have arguably the strongest career of anyone on this list? For that reason, I'm giving her the top spot! Go Sandy!
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