The She’s All That Cast Is Even More Iconic Than You Remember
When She’s All That debuted in theaters exactly 21 years ago this week, critics weren’t particularly taken with the teen rom-com. A modern-day take on My Fair Lady that swapped Edwardian London for ’90s SoCal, She’s All That follows a high school jock who makes a bet with his classmates that he can transform a dorky social pariah into a glamorous prom queen. Starring Freddie Prinze Jr. and Rachael Leigh Cook in breakout roles that earned them the highly coveted Teen Choice Award for sexiest love scene, the film was deemed “inoffensive” at best and “breezy propaganda for American high school fascism” at worst.
But that hardly mattered to the throngs of moviegoers raised on MTV and cable reruns of John Hughes classics, who made She’s All That one of the biggest hits of 1999. Grossing more than $100 million against a $10 million budget, its status has only grown as twentysomethings discover the coming-of-age classic every year. And in an era where everything ’90s is being recycled and repackaged across the culture, its datedness—both in plot and aesthetics—only works in its favor. Especially when the film in question kicks off its climatic prom scene with the entire student body performing an intricately choreographed dance to “The Rockafeller Skank” emceed by their classmate, Usher.
My apologies, did I forgot to mention Usher is in She’s All That? How about Gabrielle Union and Lil’ Kim, both making their film debuts alongside Oscar winner Anna Paquin and future Succession star Kieran Culkin? She’s All That makes a strong case for casting directors to have their own Oscar category, with then-mainstays and future A-listers rounding out its cast of then-rising stars. To celebrate 21 years of the teen classic, pop in your Sixpence None the Richer cassette: Let’s see what William Henry Harrison High School’s class of 1999 has been up to.
Photo: Getty Images; (c) Miramax / Courtesy Everett Collection1/14Freddie Prinze Jr. as Zachary “Zack” Siler
Playing resident jock and class president, Zack Siler transformed Prinze into an overnight heartthrob gracing the covers of Seventeen and Teen People. After a string of back-to-back rom-coms (Down to You, Boys and Girls, Head Over Heels), Prinze starred in the live-action reboot of Scooby Doo with Sarah Michelle Gellar. The two had previously met on the set of I Know What You Did Last Summer before dating in 2000; they got married in 2002. Prinze continues to act, having appeared in television series like Friends, Frasier, and a notoriously messy season of 24, which the actor says made him want to quit the business. A father to two children with Gellar, Prinze is also a martial artist, surfer, and self-described foodie. He even released his first cookbook, Back to the Kitchen, in 2016.
Photo: Getty Images; (c) Miramax / Courtesy Everett Collection2/14Rachael Leigh Cook as Laney Boggs
Until She’s All That, Leigh Cook was best known for destroying a kitchen with a frying pan in the infamous “This Is Your Brain on Drugs” PSA. After the film became a sleeper hit, Leigh Cook appeared in films like Josie and the Pussycats and the television series Into the West and Perception. She’s recently starred in several Hallmark Channel films and cameo’d in Khalid’s “Young Dumb & Broke” music video, as well as having a recurring role on Criminal Minds. She has two children with her former husband, actor Daniel Gillies of The Vampire Diaries fame.
Photo: Getty Images; (c) Miramax / Courtesy Everett Collection3/14Dulé Hill as Preston
As the less despicable half of Zack’s inner circle, Dulé Hill starred in She’s All That the same year he broke out portraying a presidential aide on The West Wing. He earned an Emmy nomination for that role and has starred in a successful run of television series since, including Psych, Doubt, Ballers, and Suits. Hill married his Ballers costar Jazmyn Simon in 2018 and they welcomed their first child, Levi, this past May.
Photo: Getty Images; (c) Miramax / Courtesy Everett Collection4/14Clea DuVall as Misty
Between She’s All That, But I’m a Cheerleader, and Girl, Interrupted, did anyone have a better 1999 than Clea DuVall? DuVall has stayed busy in the years since on television series like Carnivale, Veep, and American Horror Story. DuVall has become a vocal advocate for the LGBTQ+ community and played numerous queer characters. She wrote and directed the upcoming holiday rom-com Happiest Season, starring Kristen Stewart and Mackenzie Davis, out this November.
