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The Cast of ‘She’s All That’ Aged Like Fine Wine! See What The Film’s Stars Look Like Now

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Updated on: Jul 26, 2024 1:17 pm·

By Samantha Agate

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When it comes to ‘90s cult classic films, She’s All That ranks at the top of the list. The 1999 romantic comedy starring Rachael Leigh Cook and Freddie Prinze Jr. had dozens of iconic scenes and major celebrity cameos. You won’t believe what the cast of the film looks like today!

Rachel’s Laney Boggs and Freddie’s Zack Siler ultimately ended up sharing a steamy kiss at the end of the film. Their characters became unlikely friends while navigating the trials and tribulations of high school, like vying for Prom Queen and facing bullies. Their onscreen romance came with several speedbumps along the way.

Other notable stars who appeared in the 1999 version include Jodi Lyn O’Keefe, Kieran Culkin, Matthew Lillard, Usher, Lil’ Kim, Gabrielle Union and Anna Paquin.

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‘She’s All That’ Cast Photos Then and Now: See the Film’s Stars Today

Rachael Leigh Cook

After portraying Laney, Rachael went on to become one of the biggest stars on the Hallmark channel, with roles in films like Summer Love and Valentine in the Vineyard. She is also a mom to two kids, Charlotte and Theodore, whom she shares with her ex-husband, Daniel Gillies.
The Hallmark star shared a selfie with Freddie on Instagram in September 2016, with fans pointing out how the pair look like they haven’t aged at all. Rachael later joined the cast of the film’s Netflix remake called He’s All That which was released in 2021. The Minnesota native dished on why Freddie was not returning to the franchise more than 20 years after the original film’s release.
“He is doing really well. We both discussed if he was going to do this one or not,” Rachael told People in May 2021. “It ended up not being a good fit for him, but he and the creative team are behind it are totally cool.”
In July 2024, Rachael reunited with Freddie 25 years after starring together in the film. She came out to support his latest film, The Girl in the Pool. They were all smiles in photos snapped on the red carpet, proving that they continue to defy aging!

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Freddie Prinze Jr.

In 2002, Freddie starred as Fred Jones in Scooby-Doo, a role he also reprised in the 2004 sequel. He married Sarah Michelle Gellar in 2002, who also had a small non-speaking role in She’s All That. The 24 alum and the Emmy winner share two children: Charlotte and Rocky.

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Matthew Lillard

Matthew also starred in Scooby-Doo with Freddie and has voiced the character of Shaggy in dozens of animated adaptations. The Michigan native landed roles on Bosch and Good Girls before joining the cast of He’s All That. He and his wife, Heather Helm, are parents to three kids: Addison, Macey and Liam.

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Paul Walker

Before Paul’s death in 2013, he starred as Brian O’Conner in the Fast and the Furious franchise. The soap opera alum is survived by his daughter, Meadow Walker.

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Kieran Culkin

Kieran portrayed Laney’s brother, Simon Boggs, in the teen flick. The Emmy nominee began starring as Roman Roy in HBO’s Succession in 2018. He married Jazz Charton in 2013 and is a dad to kids Kinsey and Wilder.

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Kevin Pollak

Comedian Kevin Pollak played Laney’s father, Wayne Boggs, in the film. Since appearing in the movie, he has continued his career as an actor and impressionist and started a podcast. In 2017, he joined the cast of The Marvelous Mrs. Maisel.

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Usher

Usher made a cameo in She’s All That as the campus DJ. The Grammy winner recorded several bestselling hits of the 2000s including “Burn,” “Caught Up,” “My Boo” and “Yeah!”

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Gabrielle Union

Gabrielle landed the role of Katarina “Katie” Darlingson one year before her breakout role in Bring It On. The We’re Going to Need More Wine author married Dwayne Wade in 2014 and became a stepmother to his three children. In 2018 they welcomed daughter Kaavia via surrogate.

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Lil’ Kim

Lil’ Kim has made several film cameos over her years in the spotlight. In addition to the rapper’s role of Alex in She’s All That, she also appeared in Zoolander and Superhero Movie. The “No Time” singer is a mom to one daughter, Royal Reign.

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Jodi Lyn O’Keefe

Jodi’s unforgettable role of Taylor Vaughan marked one of her first roles in Hollywood. She has gone on to star in several popular television series like The Vampire Diaries, Two and a Half Men, Boston Legal and Prison Break.

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Anna Paquin

Anna’s role of Mackenzie Siler came one year before she joined the cast of X-Men. The True Blood alum won a Golden Globe award for her work on the drama series in 2009. She married costar Stephen Moyer in 2010. The couple are proud parents to twins Charlie and Poppy.