Photo Credit: The Kobal Collection / Miramax
When She's All That came out in 1999, it was one of the biggest romantic comedies to hit the big screen. Rachael Leigh Cook and Freddie Prinze Jr. seemed like the ones to watch, and we didn't see how another romcom could ever top this teen flick.
Well, 14 years have passed and things have certainly changed. Most of the biggest stars in the movie are now barely around, and some of the smaller actors -- like Dule Hill and Anna Paquin -- have gone on to be its most successful celebs.
Sure, movies like Forgetting Sarah Marshall and Silver Linings Playbook have since raised the bar in the genre -- but we'll always have a special place in our heart for the cheesy rom-coms of '90s.
Here's what's happened to the cast of She's All That.
Rachael Leigh Cook
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Rachael Leigh Cook, 33, could never really be dowdy, but she tried her hardest playing nerdy Laney Boggs in She's All That. (Although those overalls and glasses weren't nearly enough to hide her beauty!) This film was pretty much the high point of her career, as even her 2001 hit Josie and the Pussycats didn't quite top She's All That's popularity. Cook disappeared as a leading lady after Josie, primarily voice acting and taking small roles in films and TV shows. She's currently married to The Vampire Diaries star Daniel Gillies and is back on television starring in the TNT series Perception. Even happier news? Cook recently announced she is pregnant with her first child.
Freddie Prinze Jr.
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Can you remember the days when Freddie Prinze Jr. was one of the hottest men in Hollywood? So can we...but just barely. The 37-year-old was in the midst of his late '90s/early '00s popularity when he played Zack Siler in She's All That. He still had some bigger movies ahead of him after the film came out, but 2002's Scooby-Doo was the last of his big hits. After that, he gradually fell into obscurity following his marriage to costar Sarah Michelle Gellar in 2002. He's since had stints on 24 and Boston Legal, and he even worked on creative team for WWE -- but the former heartthrob has never returned to the fame he had during the 1990s.
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Matthew Lillard, 43, could probably pull off the role of Brock Hudson as well now as he did back in 1999. For those of you who don't remember, Brock was the has-been Real World reality star that Zack's girlfriend left him for at the beginning of the movie. Like his Scooby-Doo costar Prinze, Lillard was reaching his peak when She's All That came out. He already had Hackers, SLC Punk! and Scream under his belt, but it was Scooby-Doo that went on to be his biggest hit. Though Lillard never quite faded into obscurity, he has spent the past 14 years mixing small film and TV parts with Scooby-Doo voice acting gigs. He had a resurgence in recent years, taking roles in George Clooney's The Descendants and Clint Eastwood's Trouble With the Curve.
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To be honest, we barely knew who Paul Walker was when She's All That came out. The 39-year-old was simply Dean Sampson, Jr. in the film, the jerk friend of Zack's who convinced him to find a random girl and transform her into Prom Queen material. It wasn't really until 2001's The Fast and the Furious came out that Walker became a certified movie star, and he's remained on that level since. Unlike many other celebrities on the list, Walker has actually continued to get bigger (and sexier!) since She's All That came out. Unfortunately, the actor was killed in a tragic car accident on Nov. 30. RIP Paul.
Jodi Lynn O'Keefe
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Jodi Lyn O'Keefe had her five-year-long stint on Nash Bridges to thank for landing the part of Zack's ex-girlfriend Taylor Vaughan in She's All That. It was arguably the biggest film role of O'Keefe's early career, and she continued to take small parts in movies and TV shows as the years went on. O'Keefe, 34, has been steadily working in Hollywood, but her most recent noteworthy project was starring as Gretchen Morgan in the last two seasons of Prison Break.
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It's funny to look back and see how little Anna Paquin had done in her career when she starred as Zack's younger sister Mac. Sure, she was previously known as a child actress in The Piano and Fly Away Home, but it wasn't until 2000's X-Men that she truly broke out as a full-fledged star. She then went on to star in the franchise's sequels, before striking gold as Sookie Stackhouse on HBO's True Blood. There Paquin met her husband Stephen Moyer, whom she later had fraternal twins with.
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Kieran Culkin's biggest claim to fame has always been his older brother Macaulay, and he was still stuck under his shadow when he starred as Laney's brother Simon. Prior to his small role in the movie, the actor had bit parts in films such as Home Alone, Father of the Bride and their respective sequels. He's always been careful about his movie roles and has alternated between indie projects and mainstream movies. Most recently Culkin starred in Scott Pilgrim vs. the World, Margaret and the star-filled comedy Movie 43.
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If you can't remember Usher appearing in She's All That, it's because he only played the prom deejay in the movie. Of course, you likely knew exactly who he was at the time, as Usher had risen to near-instant fame following the release of his self-titled debut in 1994. In the years since, the 34-year-old has become a bigger and bigger music talent and is still a guaranteed success. Of course, we also have him to thank (or blame?) for introducing Justin Bieber to the world. Usher is currently a mentor on The Voice and is working on a new album.
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Like Usher, Kimberly "Lil' Kim" Jones was a musician whose fame got her into She's All That. The 1999 film was her first movie role, and she didn't have much to do in it beyond look cute as popular kid Alex. At the time, Lil' Kim was riding high on the success of her 1996 debut album Hard Core, and her career would continue to get bigger over the years with 2000's The Notorious K.I.M. and 2003's La Bella Mafia. Plus, who can forget her contribution to "Lady Marmalade"? After serving a year-long prison sentence in 2005, Lil' Kim has largely stayed out of the public eye, though she did make a brief reappearance when she was featured in the eighth season of Dancing with the Stars in 2009. She is currently endorsing Ciroc Vodka.
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Gabrielle Union had been dabbling on television for years before she landed her first film role in She's All That. She played one of the popular girls, Katie, who always seemed to go out of her way to be nice to Laney. Union went on to star in other turn of the millennium romances such as 10 Things I Hate About You and Love & Basketball, but she got her big break in 2000's Bring It On. She was never part of a hit quite like that again, but Union has continued to star in a string of big movies, including Bad Boys II, The Perfect Holiday and Cadillac Records -- and she also took stints on shows like Ugly Betty, Life and FlashForward. In recent years, Union starred in Steve Harvey's Think Like A Man and is the lead in BET's upcoming series Being Mary Jane.
Like Union and Lil' Kim, Dule Hill played a popular friend of Zack's. He wasn't a big star when he joined the cast, but he did continue to land decent film roles in 2000's Men of Honor and 2003's Holes. But Hill doesn't need to rely on a film career, since he's had his best luck in television. He starred as Charlie Young on The West Wing, which ran from 1999 to 2006, and he's been playing Gus on Psych since 2006.