From High School Hotties To Oscar Winner: The Shocking Current Status Of The Movie She's All That Cast

It’s been over two decades since She’s All That defined the teen romantic comedy genre, but the cast of this iconic 1999 film is making headlines in the current year, 2025, with a string of major career moves, surprising reunions, and even an Academy Award win. The classic tale of a popular jock, Zack Siler, betting he can transform the "geeky" Laney Boggs into the prom queen remains a cultural touchstone, but the lives and careers of the actors who brought the students of Fairmount High to life have evolved in spectacular and unexpected ways.

The biggest news is a major on-screen reunion, as original stars Freddie Prinze Jr. and Rachael Leigh Cook are set to co-star in an upcoming holiday film, proving their chemistry is far from over. Beyond the main couple, one supporting cast member has achieved the highest honor in Hollywood, securing his place as one of the most successful actors from the ensemble. This is a deep dive into the full She's All That cast, revealing where they are now and what they're working on in 2025 and beyond.

The Main Cast: From Prom Night to Hollywood Power Players (2025 Updates)

The core trio of the film—Zack, Laney, and the villainous Brock Hudson—have all maintained busy careers, with 2025 proving to be a particularly active year for their projects.

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• Freddie Prinze Jr. (Zack Siler): The high school heartthrob has returned to his roots in the horror genre. In 2025, Prinze Jr. is set to reprise his iconic role as Ray Bronson in the highly anticipated sequel to the 90s slasher classic, I Know What You Did Last Summer. In a surprising romantic comedy twist, he is also reuniting with his co-star Rachael Leigh Cook in the upcoming holiday film, The Christmas. He and Cook are also scheduled to appear at 90s Con in March 2026, fueling fan nostalgia.
• Rachael Leigh Cook (Laney Boggs): The actress known for her transformative "makeover" scene has become a staple in the world of romantic films. In February 2025, Cook’s newest Hallmark Channel movie, *Sisterhood Inc.*, is set to premiere. She also made a notable appearance in the 2021 gender-swapped reboot, He's All That, playing the mother of the new lead, Padgett Sawyer. Her upcoming movie with Freddie Prinze Jr., *The Christmas*, marks a major reunion for the 90s screen couple.
• Matthew Lillard (Brock Hudson): The former reality star who delivered the unforgettable "Am I a God?" monologue remains a powerhouse in both acting and voice work. Lillard continues his tenure in the horror community, having successfully launched a new franchise. He is slated to return as the villainous William Afton in the sequel, Five Nights at Freddy's 2, which is currently scheduled for release in December 2025. Lillard also had a cameo in the He's All That reboot, playing Principal Bosch.
• Paul Walker (Dean Sampson): The actor who played Zack’s arrogant friend tragically passed away in 2013. His legacy continues through his extensive filmography, most notably the *Fast & Furious* franchise. He remains a beloved figure in pop culture.
• Jodi Lyn O'Keefe (Taylor Vaughan): The actress who portrayed the high school queen bee has had a steady career in television. O'Keefe is well-known for her roles as Cassidy Bridges on *Nash Bridges*, Gretchen Morgan on *Prison Break*, and Jo Laughlin on *The Vampire Diaries*.

The Unexpected Success of the Supporting Cast

One of the most remarkable aspects of She’s All That is its deep bench of supporting talent, many of whom were just starting their careers. Several of these actors have gone on to become Oscar winners, Emmy nominees, and major stars in their own right.

Kieran Culkin’s Triumphant Oscar Win

Kieran Culkin, who played Laney’s eccentric younger brother, Simon Boggs, has achieved the highest level of critical acclaim in Hollywood. His career trajectory has been one of the most impressive of the entire cast. Culkin, already known for his Emmy-winning role in the critically acclaimed HBO series *Succession*, solidified his status as a major dramatic actor in 2025.

In a major update, Culkin won the Academy Award for Best Supporting Actor at the 2025 Oscars for his performance in the film *A Real Pain*. This victory highlights the incredible talent that was packed into the 1999 teen comedy, turning the "geek's little brother" into an Oscar-sweeping star.

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The Rise of the Fairmount High Ensemble

The film’s minor roles were filled with future stars who have since become household names in television and music.

• Anna Paquin (Mackenzie Siler): Already an Oscar winner for *The Piano* before *She's All That*, Paquin continued her success with the lead role of Sookie Stackhouse in the HBO series *True Blood*. Her recent projects include the television series *Flack* and the film *A Bit of Light*.
• Gabrielle Union (Katie): Union, who played one of Taylor Vaughan’s friends, has built a highly successful career in film and television. In 2025, she is producing and starring in an adaptation of the novel *The Perfect Find* and is also set to appear in the movie *Riff Raff*.
• Usher (Campus DJ): The R&B superstar’s cameo as the school DJ remains a memorable part of the film. In 2025, Usher continues to maintain his status as a cultural icon with ongoing musical projects, tours, and a drama series in development based on Black love in Atlanta.
• Dulé Hill (Preston): Known for his roles in *The West Wing* and *Psych*, Hill continues to work steadily in television. His recent projects include the 2024 miniseries *The Express Way with Dulé Hill* and a recurring role in the 2025 series *Good American Family*.
• Elden Henson (Jesse Jackson): The actor who played one of Laney’s quirky friends is best known for his role as Fulton Reed in *The Mighty Ducks* trilogy. In a major update for Marvel fans, Henson is set to reprise his role as Foggy Nelson in the upcoming second season of the Disney+ series *Daredevil: Born Again*.
• Lil' Kim (Dionne): The legendary rapper's cameo as one of the dancers at the party is a fan-favorite moment. In 2025, Lil' Kim is actively touring, with her music career remaining a primary focus.

The Enduring Cultural Legacy of She's All That

More than 25 years after its release, She’s All That remains a definitive piece of 90s teen cinema. Its influence goes far beyond the cast’s individual careers, shaping the romantic comedy landscape for decades.

The Iconic Soundtrack and The Montage

No discussion of the film is complete without mentioning the song that defined the makeover montage: "Kiss Me" by Sixpence None The Richer. The song became inextricably linked to the film's most iconic scene, where Laney descends the stairs in her red dress, solidifying its place as one of the most recognizable needle-drops in movie history. The music perfectly captured the film's blend of sincerity and high school drama, becoming an LSI keyword for the film itself.

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The Gender-Swapped Reboot: He's All That

The film’s enduring popularity led to the 2021 Netflix reboot, *He's All That*. This modern, gender-swapped version starred TikTok personality Addison Rae as the popular girl, Padgett Sawyer, who accepts a challenge to turn the school's biggest outcast, Cameron Kweller (Tanner Buchanan), into the new prom king. The reboot paid homage to the original by bringing back Rachael Leigh Cook in a new role as Padgett's mother, Anna Sawyer, and Matthew Lillard as Principal Bosch, connecting the new generation to the original classic.

A Nostalgic Look at the 90s Teen Rom-Com

The film is often cited as the peak of the late 90s teen movie boom, which also included hits like *10 Things I Hate About You* and *Cruel Intentions*. While the central premise—that a girl needs to remove her glasses and change her clothes to be "beautiful"—is often criticized in modern discussions, the film is also celebrated for its ensemble cast and its heartfelt, if cliché, portrayal of high school life. The film's legacy is a complex one, celebrated for its nostalgia while its themes are critically re-evaluated through a modern lens.

The current career success of the She’s All That cast, especially the Oscar win for Kieran Culkin and the reunion of Freddie Prinze Jr. and Rachael Leigh Cook, proves that the film was a launchpad for some of Hollywood’s most enduring talent. From the halls of Fairmount High to the Academy Awards stage, the stars of this 90s classic are, indeed, still all that.