In 1999, “She’s All That” dazzled audiences with its hip take on the old Pygmalion story. The movie’s ensemble cast has since accomplished much in their careers and personal lives.
Rachael Leigh Cook: From Laney Boggs to Producer
Rachael Leigh Cook played Laney Boggs, the nerdy artist who gets a glamorous makeover. After the movie’s success, Cook starred in “Josie and the Pussycats” and provided voice work for “Robot Chicken.” She also starred in many Hallmark Channel movies. Cook debuted as a producer and actress in Netflix’s 2021 movie, “Love, Guaranteed.” She also recently acted as the protagonist’s mother in “He’s All That,” a gender-swapped reboot of the original film.
Freddie Prinze Jr.: From Heartthrob to Family Man
Freddie Prinze Jr. starred as Zack Siler, the popular jock with a bet on the line to turn Laney into the prom queen. After “She’s All That,” Prinze Jr. also appeared in the live-action “Scooby-Doo” movies with Sarah Michelle Gellar, whom he married in 2002. The couple has two children. Prinze Jr. also performed voice work for “Star Wars Rebels” and “Star Wars: The Bad Batch.” He also appeared in the “Punky Brewster” reboot cast in 2021.
Matthew Lillard: Embracing Diverse Roles
Matthew Lillard played Brock Hudson, an egotistical reality TV star. After “She’s All That,” Lillard became known as Shaggy in the “Scooby-Doo” films, a character he has continued to voice in multiple animated projects. He also starred in television series like “Bosch,” “Twin Peaks” and “Good Girls.” Lillard returned to high school for 2021’s “He’s All That,” where he played Principal Bosch.
Anna Paquin: From Supporting Role to Leading Lady
Mackenzie Siler, Zack’s wise younger sister, was played by Anna Paquin. Paquin was already an Academy Award winner for “The Piano,” and she continued to build her career with roles in the “X-Men” series as Rogue and as Sookie Stackhouse in HBO’s “True Blood.” She also starred in Martin Scorsese’s “The Irishman” and the Amazon Prime series “Modern Love.”
Kieran Culkin: From Child Actor to Emmy Nominee
Kieran Culkin played her playful younger brother, Simon Boggs. After “She’s All That,” Culkin went on to star in movies like “The Cider House Rules” and “Scott Pilgrim vs. the World.” He found critical success by playing the character Roman Roy in HBO’s “Succession,” receiving multiple nominations from the Emmys.
Dulé Hill: From Supporting Actor to Series Regular
Dulé Hill portrayed Preston, one of Zack’s best friends. After the film, Hill went on to play Charlie Young on “The West Wing” and later Burton “Gus” Guster on “Psych.” He also had roles on “Ballers” and “Suits,” and reprised his character for the “Psych” TV movies.
Gabrielle Union: From Ensemble Cast to Leading Roles
Gabrielle Union played Katie, one of the popular cliques. She made her film debut in “She’s All That,” followed by roles in “10 Things I Hate About You,” “Bring It On” and “Bad Boys II.” Union had a starring role in the BET series “Being Mary Jane,” and also co-created and starred in “L.A.’s Finest.”
Jodi Lyn O’Keefe: From High School Queen to Television Regular
Jodi Lyn O’Keefe as Taylor Vaughan, Zack’s self-absorbed ex-girlfriend. Post-film, O’Keefe starred in series like “Nash Bridges,” “Prison Break” and “The Vampire Diaries.” She also started her jewelry brand, Queen George Clothing.
Paul Walker: A Legacy Remembered
Paul Walker played Dean Sampson, Zack’s scheming best friend. Walker gained worldwide fame playing Brian O’Conner in the “Fast & Furious” series. Sadly, he died in a car crash in 2013, aged 40. His memory lives on with his films and the Paul Walker Foundation.
Since the movie’s release, the “She’s All That” ensemble has followed different trajectories, demonstrating their abilities in a range of show-business arenas.
