When She’s all That debuted in theaters precisely 21 years back this week, critics weren’t an especially taken through the teen rom-com. A modern take on My same Lady that swapped Edwardian London for ’90s SoCal, She’s all That adheres to a high institution jock who provides a bet with his classmates that he have the right to transform a dorky social pariah into a glamorous prom queen. Starring Freddie Prinze Jr. And also Rachael Leigh chef in breakout duties that earned lock the highly desire Teen an option Award for sexiest love scene, the movie was reputed “inoffensive” at best and “breezy propaganda because that American high college fascism” at worst.

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But that hardly mattered to the throngs of moviegoers elevated on MTV and cable reruns of john Hughes classics, who made She’s every That among the greatest hits the 1999. Grossing much more than $100 million versus a $10 million budget, that is status has actually only grown as twentysomethings find the coming-of-age standard every year. And also in one era where everything ’90s is being recycled and also repackaged throughout the culture, that datedness—both in plot and aesthetics—only works in that is favor. Particularly when the film in concern kicks turn off its climatic prom scene with the whole student body performing an intricately choreographed dance to “The Rockafeller Skank” emceed by their classmate, Usher.

My apologies, did i forgot to cite Usher is in She’s every That? How about Gabrielle Union and also Lil’ Kim, both making their film debuts together Oscar winner Anna Paquin and future Succession star Kieran Culkin? She’s all That makes a solid case for casting directors to have actually their very own Oscar category, through then-mainstays and also future A-listers round off out its actors of then-rising stars. Come celebrate 21 years of the teen classic, popular music in your Sixpence nobody the Richer cassette: Let’s view what wilhelm Henry Harrison High School’s class of 1999 has actually been increase to.


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Freddie Prinze Jr. Together Zachary “Zack” Siler


Playing resides jock and also class president, Zack Siler transformed Prinze right into an overnight heartthrob gracing the consists of Seventeen and also Teen People. After a cable of back-to-back rom-coms (Down come You, Boys and also Girls, Head end Heels), Prinze starred in the live-action reboot that Scooby Doo through Sarah Michelle Gellar. The two had previously met on the collection of I know What girlfriend Did critical Summer before dating in 2000; they obtained married in 2002. Prinze continues to act, having appeared in television series like Friends, Frasier, and also a notoriously messy season of 24, which the actor states made him want to stop the business. A dad to two kids with Gellar, Prinze is additionally a martial artist, surfer, and also self-described foodie. He also released his first cookbook, Back to the Kitchen, in 2016.


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Rachael Leigh cook as Laney Boggs


Until She’s every That, Leigh chef was ideal known for damaging a kitchen with a frying pan in the notorious “This Is Your mind on Drugs” PSA. ~ the film ended up being a sleeper hit, Leigh Cook showed up in films like Josie and also the Pussycats and also the television series Into the West and also Perception. She’s freshly starred in numerous Hallmark Channel films and also cameo’d in Khalid’s “Young Dumb & Broke” music video, as well as having a recurring role on Criminal Minds. She has actually two youngsters with her former husband, actor Daniel Gillies that The Vampire Diaries fame.


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Dulé Hill as Preston


As the less despicable half of Zack’s within circle, Dulé Hill starred in She’s every That the very same year he damaged out depicting a presidential aide on The West Wing. He earned an Emmy nomination because that that role and has actually starred in a effective run that television series since, consisting of Psych, Doubt, Ballers, and Suits. Hill married his Ballers costar Jazmyn Simon in 2018 and they invited their an initial child, Levi, this previous May.


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Clea DuVall as Misty


Between She’s every That, But ns a Cheerleader, and also Girl, Interrupted, walk anyone have actually a better 1999 than Clea DuVall? DuVall has stayed busy in the years since on television series like Carnivale, Veep, and also American fear Story. DuVall has become a vocal advocate for the LGBTQ+ community and also played many queer characters. She wrote and directed the upcoming vacation rom-com Happiest Season, starring Kristen Stewart and also Mackenzie Davis, the end this November.


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Anna Paquin together Mackenzie “Mac” Siler


Paquin starred together Zack’s wise-beyond-her-years boy sister in She’s all That, 6 years after winning an Oscar because that her exhilaration debut in The Piano. She didn’t slow down ~ that, starring together teenage mutant Rogue in the X-Men franchise and winning a gold Globe for her duty on the HBO vampire noir True Blood. A vocal support for the LGBTQ+ community and openly bisexual, Paquin has actually been married to her True Blood costar Stephen Moyer due to the fact that 2010, with whom she has actually twins. Paquin recently starred in the last season the Showtime’s The Affair and also had a pivotal role in boy name Scorsese’s Oscar-nominated epic The Irishman.


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Jodi Lyn O’Keefe together Taylor Vaughn


O’Keefe take it on queen bee Taylor Vaughn, who provides high school a living hell because that Laney Boggs top top her quest to victory prom queen. Having currently starred on the fight procedural drama Nash Bridges native 1996 to 2001, O’Keefe go on to show up in collection like Charmed, Boston Legal, and Prison Break. She recently had actually a recurring duty on the CW hit The Vampire Diaries in addition to to run her very own clothing and jewelry lines. And as if that doesn’t keep her busy enough, O’Keefe is additionally a licensed bounty hunter.


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Kieran Culkin as Simon Boggs


Kieran Culkin reduced his teeth acting alongside older brothers Macaulay in several films prior to making a surname for himself after She’s all That. After starring in The Cider house Rules and also earning a golden Globe nomination for his starring function in Igby walk Down, Culkin take it a break from the huge screen to emphasis on doing theater in new York and also London. After returning with duties in Scott Pilgrim vs. The World and the FX series Fargo, Culkin now stars as a an especially slimy member of the dysfunctional Roy household on the HBO hit Succession. He and also his wife, Jazz Charton, welcomed very first child, Kinsey, this previous September.


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Matthew Lillard together Brock Hudson


Playing a self-obsessed former Real World contestant in She’s all That, Lillard had actually a knack for play ’90s boneheads across hits choose Serial Mom and Scream. Lillard reunited with Prinze in the live-action Scooby-Doo movie series, play a an ext lovable goofball this time about as Shaggy. He’s continued to voice the lovely cartoon personality in numerous animated films and series since, and making appearances in everything from Twin Peaks: The Return to Good Girls. He is married with 3 children.


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10/14

Lil’ Kim as Alex Chason Sawyer


Lil’ Kim was currently well ~ above her means to rap royalty status once she make her acting debut in She’s every That as among Taylor’s high college BFFs. 2 years later she’d struggle No. 1 and also win a Grammy for “Lady Marmalade” v Mya, Pink, and also Christina Aguilera. She go on to appear in numerous television shows and films, however mostly exit music before she served a year-long jail sentence in 2005. She exit 9, her an initial album in 15 years, in 2019 and is working on a follow-up, due part time later this year.


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Milo Ventimiglia together Soccer Player


When Laney tells Zack she can’t hang out due to the fact that she needs to clean the house, he provides the JV football team come over and also do it because that her. Watch closely and also you’ll clues a blink-and-you’ll-miss-it appearance by Milo Ventimiglia as one of the soccer players, in among his faster appearances. After break out together Jess top top Gilmore Girls, Ventimiglia played Sylvester Stallone’s boy in Rocky Balboa and Peter Petrelli in Heroes. He currently stars together prime time’s favorite patriarch ~ above the NBC weepie This Is Us v Mandy Moore.


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Paul pedestrian as Dean Sampson, Jr.


Films prefer Pleasantville, Varsity Blues, and She’s every That made walker a family name; the starred in the latter as the cocksure jock who convinces Zack to offer Laney a makeover before trying to woo her later on on. But it to be his function in the Fast and also Furious franchise that would certainly make him a family name. While shooting Furious 7 in 2013, walker tragically died in a auto accident at 40 years of age. 


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Usher as Campus DJ


Usher to be a already a Billboard fixture v several optimal 10 hits by the moment he showed up in She’s every That together the campus DJ. He’d walk on come to come to be one of the best-selling artists of all time, v his 2004 LP Confessions selling 20 million copies and also producing 4 No. 1 hits. If music has constantly been his main prerogative, Usher’s made a handful of appearances throughout film and television over the years, most recently as himself through a memorable cameo in 2019’s Hustlers.


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Sarah Michelle Gellar together Girl in Cafeteria


Gellar to be shooting Buffy the Vampire Slayer once she came to visit she close friend—and future husband—Prinze ~ above the collection of She’s all That. manager Robert Iscove request Gellar to carry out a small cameo, i m sorry she agreed to as lengthy as there were no speak lines. After appearing in the iconic function of “Girl in Cafeteria,” Gellar scored films like Cruel Intentions, The Grudge, and the live-action Scooby-Doo remake. Gellar proceeds to act yet in current years has also been concentrated on her baking-kit startup Foodstirs and raising she two children with Prinze.

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