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Released in 1999, She’s All That left a lasting cultural legacy, becoming a quintessential teen rom-com beloved by millennials everywhere. It epitomizes the late ’90s high school experience with its portrayal of cliques, prom culture, and the power of love. Of course, we can’t reminisce about She’s All That without mentioning its stars Freddie Prinze Jr. and Rachael Leigh Cook. On July 24, the former co-stars reunited, notably 25 years after their career-making film premiered.

Freddie Prinze Jr. and Rachael Leigh Cook film a scene for She's All That together
‘She’s All That’ stars Freddie Prinze Jr. and Rachael Leigh Cook film a scene for the 1999 movie together | Miramax via Youtube

She’s All That popularized the “makeover” trope, where an “ugly duckling” is transformed into a swan. Its soundtrack, featuring iconic songs like Sixpence None the Richer’s “Kiss Me,” became synonymous with the era. Prinze Jr. had already established himself with 1997’s I Know What You Did Last Summer. But his role as Zack Siler in She’s All That solidified his place as an early-aughts teen heartthrob. Cook also saw her acting career take off. She went on to star in 2001’s Josie and the Pussycats, which many argue has become a cult classic.

2000s heartthrobs Rachael Leigh Cook, Freddie Prinze Jr., and Sarah Michelle Gellar pose in 2000
Rachael Leigh Cook in 2000; Sarah Michelle Gellar and actor Freddie Prinze Jr. in 2000 | SGranitz/WireImage; Ron Galella/Contributor

Prinze Jr. has dabbled in acting since marrying his wife, Sarah Michelle Gellar, and starting a family. However, few of his roles have seen the success of his late ’90s/early 2000s hits. This is one reason why fans of the 48-year-old are eagerly anticipating his turn in The Girl in the Pool. At the psychological thriller’s premiere on July 24, Prinze Jr. celebrated with the cast, Gellar, and supporters, like Cook.

2000s heartthrobs Rachael Leigh Cook, Freddie Prinze Jr., and Sarah Michelle Gellar pose together in 2024
Rachael Leigh Cook, Freddie Prinze Jr., and Sarah Michelle Gellar at ‘The Girl In The Pool’ premiere | Paul Archuleta/Getty Images

The Girl in the Pool follows a well-to-do family man who is forced to struggle through a surprise birthday party moments after hiding the murdered corpse of his mistress. Prinze Jr. explained to Us Weekly how he felt about starring on the silver screen again. “The amount of responsibility on you as the lead in that kind of a film … Everybody’s depending on you to be there and be at your best. So I put a lot of pressure on myself to be that guy. I knew the responsibility of this character … I put a lot into him.”

Wearing a black jacket, Freddie Prinze Jr. attends the Los Angeles premiere of "The Girl In The Pool"
Freddie Prinze Jr. at the ‘The Girl In The Pool’ premiere on July 24, 2024 | Paul Archuleta/Getty Images

Always beautifully understated, Cook, now 44, wore an off-the-shoulder white sweater, straight-leg jeans, and simple brown boots. Prinze Jr. had a “cool dad” look as the father of two opted for a black bomber jacket and red Nike sneakers. E! News posted a fun Instagram video of the pair over the years. Supporters took the comment section, writing, “Such a sweet movie!!! Love them both,” and “Both of them are still gorgeous.”

Actors Rachael Leigh Cook, Freddie Prinze Jr., and Sarah Michelle Gellar stand together for a photo in 2024
Rachael Leigh Cook, Freddie Prinze Jr., and Sarah Michelle Gellar at ‘The Girl In The Pool’ premiere | Paul Archuleta/Getty Images
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This group of early 2000s heartthrobs recognizes the toll that stardom takes on actors. Prinze Jr. credits Gellar with helping him get out of his comfort zone for The Girl in the Pool. “If we didn’t support one another, we wouldn’t have lasted very long,” Prinze Jr. told Us Weekly. “So, when she sees me excited to do something new and different, she’s excited for her man to get to show people what he can do.”