She’s All That remains one of those timeless teen flicks, even after 22 years. The film was released on Jan. 29, 1999. The movie was a modern-day twist on George Bernard Shaw’s play Pygmalion and the 1964 film My Fair Lady. In the years since its release, She’s All That has become one of the quintessential teen rom-coms.
After two decades, She’s All That is getting a reboot. TikTok star Addison Rae, 20, will star in the gender-swapped reboot alongside Cobra Kai’s Tanner Buchanan, according to Variety. Original star Rachael Leigh Cook, 41, will play Addison’s mom in the film. In honor of the She’s All That’s 22nd anniversary and the upcoming reboot, take a look back at the original cast then and now.
Rachael Leigh Cook
Rachael Leigh Cook became a rom-com princess after playing Laney Boggs in She’s All That. In the years since the movie’s release, Rachael has starred in films like Josie and the Pussycats, voiced multiple characters in the series Robot Chicken, and appeared in several Hallmark films. She recently returned to the rom-com genre with the 2020 Netflix film Love, Guaranteed. She starred and produced the film.
The actress married actor Daniel Gillies, 44, in 2004. They have two kids together. The couple split in 2019. Daniel filed for divorce in July 2020, PEOPLE reported.
Freddie Prinze Jr.
Freddie Prinze Jr., now 44, was one of the ultimate heartthrobs of the late ’90s and early ’00s. He starred as Zack Siler in She’s All That. His films following She’s All That included Summer Catch, the live-action Scooby Doo and its sequel, Head over Heels, and more. He notably guest-starred in a 2002 episode of Friends. He also starred in TV shows like Boston Legal, Freddie, 24, and voiced Kanan Jarrus in Star Wars Rebels. He’s returning to TV in the Punky Brewster revival on Peacock.
Freddie married fellow actress Sarah Michelle Gellar, 43, in 2002. They had met while filming I Know What You Did Last Summer. They have two kids.
Paul Walker
Paul Walker starred as Dean, Zack’s best friend. The same year as She’s All That, Paul also starred in the teen cult classic Varsity Blues. Paul became a global star playing Brian O’Connor in The Fast and the Furious in 2001.
The actor was in the middle of filming the seventh film in the Fast & Furious franchise when he was killed in Nov. 2013 in a single-car crash. Paul was just 40 years old. He hadn’t completed filming for Furious 7 yet, so his brothers Cody and Caleb partially filled in for him. Furious 7 was his final film role. Paul has a daughter, Meadow, 22, from a past relationship.
Gabrielle Union
Gabrielle Union, 48, played Katie Darlingson, one of Taylor Vaughan’s BFFs. She’s All That marked Gabrielle’s feature film debut. She starred in another teen rom-com in 1999, 10 Things I Hate About You. Her other major films include Bring It On, Love & Basketball, Deliver Us From Eva, Bad Boys II, Think Like A Man, and more.
From 2013 to 2019, she starred as Mary Jane Paul in the series Being Mary Jane and the subsequent TV film. The role earned her an NAACP Image Award for Outstanding Actress in a Television Movie, Mini-Series or Dramatic Special. She served as a judge for one season of America’s Got Talent and recently starred in the Bad Boys TV spinoff, L.A.’s Finest, with Jessica Alba, 39. She will next star in the Disney+ reimagining of Cheaper by the Dozen with Zach Braff, 45.
Gabrielle married NFL player Chris Howard, 45, in 1991. Their divorce was finalized in 2006. She married NBA player Dwyane Wade, 39, in 2014. Their daughter, Kaavia, 2, was born via surrogate in 2018.
Jodi Lyn O’Keefe
Jodi Lyn O’Keefe, 42, played the stuck-up high school drama queen Taylor Vaughan. She went on to star as Gretchen Morgan in Prison Break from 2007 to 2009. She then went on to join The Vampire Diaries from 2014 to 2017. Jodi also starred in Hit The Floor from 2014 to 2018. Jodi reprised her Vampire Diaries role in a 2018 episode of the TVD spinoff Legacies. She is also a licensed bounty hunter, according to her Twitter.
Matthew Lillard
Like many of his She’s All That co-stars, Matthew Lillard, 51, was one of the most prominent younger stars of the late ’90s. He starred as Brock Hudson in the 1999 teen rom-com. He reunited with Freddie in the 2001 teen flick Summer Catch, as well as the live-action Scooby Doo movies. Matthew played Shaggy, while Freddie played Fred. Matthew has continued to voice the role of Shaggy in animated projects since 2009.
His other film roles include Without a Paddle, Trouble with the Curve, Match, The Descendants, and more. He’s currently starring as Dean in the NBC series Good Girls, which has been renewed for a fourth season. He’s been married to Heather Helm since 2000. They have three kids together.
Lil’ Kim
Lil’ Kim, 46, played Alex Sawyer in She’s All That. Lil’ Kim became one of the most prominent female rappers over the course of the ’90s. She’s gone on to release 4 studios since 1999. Her latest, 9, was released in 2019. She was featured on the hit 2001 single “Lady Marmalade,” which was recorded for the Moulin Rouge! soundtrack.
In 2005, Lil’ Kim was sentenced to one year in prison for lying to a federal grand jury about a friends’ involvement in a 2001 shootout, TODAY reported. She was released in July 2006. The rapper had her own reality series about the sentence, Lil’ Kim: Countdown to Lockdown. She was also a celebrity on season 8 of Dancing with the Stars. She gave birth to a daughter, Royal Reign, in 2014.
Usher
Usher, 42, played the Campus DJ in She’s All That. The film wasn’t his first role or his last. The same year as She’s All That, Usher had the leading role in the movie Light It Up. He recently appeared as himself in the 2019 film Hustlers. His focus has mainly been on music over the years. His fourth studio album, Confessions, was released in 2004 and became a monster hit. The album featured classics like “Yeah!,” “Burn,” “Confessions Part II”, and “My Boo.” As of 2018, Usher has released 8 studio albums. He was also a coach for seasons 4 and 6 of The Voice.
Usher notably dated TLC member Chilli Thomas, 49, from 2001 to 2003. He married stylist Tameka Foster, 50, in 2007. They have two kids together. They divorced in 2009. He married Grace Miguel, 51, in 2015. They divorced in 2018. Usher is currently dating Jenn Goicoechea, 36, and their daughter was born in Sept. 2020.
Kieran Culkin
Kieran Culkin, 38, starred as Simon Boggs, Laney’s younger brother. Kieran knows a thing or two about being a younger brother. He’s the real-life younger brother of Macaulay Culkin, 40. A couple of years after She’s All That, Kieran earned critical acclaim for his performance in the 2002 Igby Goes Down. He was nominated for a Best Actor Golden Globe Award. He also played Wallace Wells in Scott Pilgrim vs. the World.
He has since transitioned to television. He played Rye Gerhardt in season 2 of Fargo. He’s currently playing Roman Roy in the hit HBO series Succession. He’s received two Golden Globe nominations for Best Supporting Actor and a Primetime Emmy nomination. The show is in the midst of filming its third season. Kieran married Jazz Charton in 2013. Their daughter was born in 2019.
Anna Paquin
Anna Paquin, 38, starred as Mac Siler, Zack’s younger sister. The Oscar winner went on to play Rogue in multiple films in the X-Men franchise. She rose to worldwide fame playing Sookie Stackhouse in the HBO series True Blood from 2008 to 2014. She won the Golden Globe for Best Performance by an Actress in a Television Series — Drama in 2014. Her other notable films include Bury My Heart at Wounded Knee and The Irishman. She’s currently starring in the Amazon Prime Video series Flack, which has been renewed for season 2.
Anna met and fell in love with her True Blood co-star Stephen Moyer, 51. The couple married in 2010. Anna gave birth to twins in 2012.