Believe it or not, everyone's favorite bespectacled-loser-turns-into-contact-wearing-popular-girl chick flick, She's All That, is fifteen years old. Happy almost sweet sixteen, you modern fairytale.
She's All That, in case you don't remember (and why wouldn't you?), is a film about an artsy loser (Rachael Leigh Cook) who becomes the subject of a bet, in which a popular jock with a secret soft spot for weird girls (Freddie Prinze Jr.) wagers that he can get the "ugliest girl in school" (Cook) to be crowned prom queen. There's is also some business about his ex, her new guy (Matthew Lillard) incredibly loosely based on Puck from The Real World, and some decision about choosing Harvard or Yale or something. Teen boys of the '90s did NOT want to go to the colleges their parents wanted them to. The one thing for certain is that Prinze needs to prove to his bros that he is still the man. Does he win the bet? Does it matter?
Obviously, it's super easy to make Rachael Leigh Cook look hot, a montage-based task accomplished by Anna Paquin as Prinze's sister. Cook gets popular, Prinze gets smitten, ex-girlfriend gets schemey, pretty sure someone gets thrown/falls into a pool, all leading up to the point when Cook learns about the bet and feels ridiculed and shamed. But then remorseful jock (Freddie Prinze Jr.) pouts at her and sweet-talks her until she forgives him his past travails and they live happily ever after.
Like the best 1990s rom-coms that focus on high school drama, She's All That is full of stars that time's forgotten -- and some are actually still pretty famous today. In honor of the beloved flick's coming of age, here's our roundup of the stars, and not-so stars, that appeared in She's All That -- and what they're up to today.
Rachael Leigh Cook -- Cook nabbed a lead role across Tara Reid and Rosario Dawson in Josie and the Pussycats in 2001, but sort of plateaued after that. She appeared in some episodes on Psych and other shows but never starring in a popular movie again. She's married to The Vampire Diaries actor Daniel Gillies, and they have a normally-named daughter.
Freddie Prinze Jr. -- Prinze rode the teen heart-throb wave for a while after She's All That, starring in Down to You, Head Over Heels, Summer Catch and our personal favorite, Scooby-Doo. He was also featured in a few episodes of 24 and something called Freddie. Prinze somehow segued into a career in WWE blogging, and worked for the wrestling company for a year from 2008-2009. He returned to WEE as a producer and director and has been working there ever since. He's married to rom com starlet Sarah Michelle Prinze (nee Gellar), the Daphne to his Fred.
Matthew Lillard -- Lillard also starred in Scooby-Doo (as Shaggy, duh) and then went kind of Scooby crazy, appearing in a number of Scooby shorts that we've never heard of. He was also in a couple of movies, including Without a Paddle.
Lil' Kim -- Lil' Kim basically played Lil' Kim in this movie. She's still mostly just being Lil' Kim today, which includes allegedly having had a lot of plastic surgery and is being sued over a zombie photo.
Anna Paquin -- Arguably the most successful actor of the lot, Paquin played Prinze's little sister in She's All That. Immediately after She's All That, she played a passionate groupie in Almost Famous and later mutant superhero Rogue in the X-Men franchise. She now stars on HBO's True Blood as vampire lover Sookie Stackhouse. She also played Jeff Daniels's quirky love interest in The Squid and the Whale, earning her indie bona fides in Noah Baumbach's acclaimed film.
Kieran Culkin -- Kieran, who plays Cook's younger brother, enjoyed a fruitful indie career following She's All That (and, lest we forget, as Macaulay Culkin's cousin in Home Alone). He was featured in Academy-Award-winningThe Cider House Rules, played Igby in indie darling Igby Goes Down and opposite Michael Cera in the vastly underrated Scott Pilgrim Vs. the World.
Usher -- Usher played the DJ in She's All That. Now he's Usher.
Gabrielle Union -- Union, who played one of the popular girls, has had a busycareer since She's All That . She appeared Love and Basketball and played opposite Kirsten Dunst in Bring It On. She also was featured in Ten Things I Hate About You, just before She's All That, which essentially makes her high school chick flick royalty.
Dulé Hill -- Hill, a popular dude in She's All That, went on to play our favorite character on The West Wing, presidential body man and boyfriend-in-law Charlie. Currently, he stars in Psych.
Tim Matheson -- Matheson plays Prinze's dad, and also graduates to a role on The West Wing as Martin Sheen's vice president. He was later on an directed episodes of Burn Notice and Hart of Dixie, and (weirdly enough) played a part in a Scooby-Doo series from 2012-2013. His real success came before She's All That, when he played in Animal House and
Milo Ventimiglia -- Ventimiglia didn't have much of a part in She's All That (IMDB tells us he's billed as "soccer player,") but went on to have a rather successful career in TV. He played across Alexis Bledel on Gilmore Girls and Peter Petrelli on Heroes.
Clea DuVall -- DuVall, who plays a mean but artsy (shocker!) girl in She's All That, went on to play edgier roles in But I'm a Cheerleader, Girl Interrupted and Argo. She was also on Heroes and American Horror Story.
Paul Walker -- Walker, who was killed in a car accident late last year, was best known for his role as Brian O'Conner in the Fast and Furious movies. He also starred in The Skulls shortly after playing a popular guy in She's All That.
This article is from the archive of our partner The Wire.