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The Ultimate 'She's All That' Cast Update: Where Are Laney, Zack, And The Rest Of The Class Of '99 Now?

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The iconic 1999 teen romantic comedy, She's All That, remains a cultural touchstone 25 years later, defining the high school movie genre with its unforgettable makeover trope and the legendary "Kiss Me" scene. As of December 22, 2025, the careers of its sprawling, star-studded ensemble—which included future A-listers and Oscar winners—have taken fascinating and often surprising turns, ranging from major horror franchise returns to critically acclaimed prestige dramas and a highly anticipated on-screen reunion.

The film, a modern retelling of George Bernard Shaw's *Pygmalion*, launched or cemented the careers of nearly every young actor on its roster. While the original 1999 classic received a gender-flipped reboot, *He's All That*, the original cast members are proving that their star power is far from a relic of the past, with several having major new projects hitting screens in 2025 and 2026.

The Core Cast: Full Biography and Latest 2025 Projects

The central love story between Zack Siler and Laney Boggs is what anchored the film, but the supporting players—from the villainous Taylor Vaughan to the scene-stealing Brock Hudson—are what made it a true ensemble classic. Here is a look at the main actors' full biographical profiles and their most current career updates.

  • Freddie Prinze Jr. (Zack Siler)
    • Born: March 8, 1976, Los Angeles, California, U.S.
    • Latest Update: The king of late-'90s teen cinema is officially making a major return to his horror roots, reprising his role as Ray Bronson in the upcoming sequel to I Know What You Did Last Summer. Furthermore, he is set to co-star with his former on-screen love, Rachael Leigh Cook, in an upcoming holiday film titled The Christmas, marking a highly anticipated reunion for the duo.
  • Rachael Leigh Cook (Laney Boggs)
    • Born: October 4, 1979, Minneapolis, Minnesota, U.S.
    • Latest Update: Cook has become a prolific producer and star in the romantic comedy and holiday movie space. She is starring in the upcoming Hallmark movie Sisterhood, Inc., a romantic drama movie, and will also co-star with Freddie Prinze Jr. in the holiday film The Christmas. She previously pitched, produced, and starred in the successful 2020 Netflix film Love Guaranteed.
  • Matthew Lillard (Brock Hudson)
    • Born: January 24, 1970, Lansing, Michigan, U.S.
    • Latest Update: Lillard is arguably having a career resurgence, often referred to as a "Lillard-aissance." He is reprising his role as William Afton in the massively popular horror sequel, Five Nights at Freddy's 2 (FNAF 2), which is set for a 2025 release. He is also slated to star in the upcoming Stephen King adaptation, *The Life of Chuck*, and is expected to return for *Scream 7*, despite his character's previous on-screen demise.
  • Jodi Lyn O'Keefe (Taylor Vaughan)
    • Born: October 10, 1978, Cliffwood Beach, New Jersey, U.S. [cite: 15 (from step 2)]
    • Latest Update: After playing the ultimate high school villain, O'Keefe continued her career in television with major roles in hit series like Nash Bridges, Prison Break (as Gretchen Morgan), and The Vampire Diaries (as Jo Laughlin). [cite: 8 (from step 2)] While her recent work includes the 2021 film He's All That, her previous television roles are still trending on streaming platforms in 2024.

The Scene-Stealers: From Oscar Winners to Marvel Stars

One of the most remarkable aspects of She's All That is the sheer number of actors who went on to become major stars, proving the film was a true launchpad for talent. These actors, who had smaller but memorable roles, have had some of the most critically acclaimed and commercially successful careers in Hollywood.

Kieran Culkin (Simon Boggs)

Laney's younger brother, Simon, was played by Kieran Culkin, who has since become a multiple award-winning actor. After his memorable role in *Succession* as Roman Roy, Culkin is highly sought after. His upcoming projects include the film *A Real Pain* and a new ensemble film from director Nancy Meyers, which is set to begin shooting in May 2026. He also continues his voice work in animated series like *Solar Opposites* (2025).

Anna Paquin (Mackenzie Siler)

Oscar-winner Anna Paquin, who played Zack's sister, Mackenzie, already had an Academy Award before appearing in the film. Her career remains robust, with recent projects including the film *A Bit of Light*, which she previewed with her husband, Stephen Moyer, in late 2025. Paquin is celebrated for her powerful roles in television, notably in *True Blood* and *Flack*.

Gabrielle Union (Katrina)

Gabrielle Union, who played one of Taylor Vaughan's friends, Katrina, has built a powerful career as an actress, producer, and author. Union is starring in the upcoming star-studded movie *Riff Raff* and is involved in a new documentary focusing on leading Black actors in Hollywood. Her continued work in film and as a published author of two memoirs and two children's books makes her a significant figure in the industry.

The Legacy: Paul Walker, Elden Henson, and Dulé Hill

The film's impact is also felt through the enduring careers and legacies of other key supporting cast members, each of whom has found massive success in different areas of entertainment, from blockbuster franchises to prestige theatre.

Paul Walker (Dean Sampson, Jr.)

The late Paul Walker, who played the arrogant Dean Sampson, Jr., cemented his legacy as one of Hollywood's biggest action stars in the *Fast & Furious* franchise. Walker tragically passed away in 2013, but his role in *She's All That* is a beloved early entry in his filmography, showcasing his ability to play both charming and villainous roles before becoming a global icon.

Elden Henson (Jesse Jackson)

Elden Henson, who played Laney’s best friend, Jesse Jackson, has become a fixture in major franchises. After starring in *The Mighty Ducks* trilogy, he gained a new wave of fans as Foggy Nelson in the Marvel Cinematic Universe series *Daredevil*. [cite: 10, 13 (from step 2)] His most current project is reprising his role in the highly anticipated 2025 series Daredevil: Born Again, a major production for Disney+.

Dulé Hill (Preston)

Dulé Hill, who played Zack's friend Preston, has had a highly successful career in both television and theatre. Best known for his long-running roles in *The West Wing* and *Psych*, Hill is currently starring in the new play *Lights Out: Nat “King” Cole*, where he plays the legendary Nat King Cole. This major New York Theatre Workshop production is running through Spring 2025, demonstrating his versatility on stage and screen.

More Than Just a High School Movie: The Cultural Entity

The enduring popularity of She's All That lies not just in its cast, but in its self-aware embrace of teen movie clichés. The film is often cited alongside other late-'90s classics like *Cruel Intentions* and *10 Things I Hate About You*. Its clever dialogue, memorable soundtrack (featuring Sixpence None The Richer's "Kiss Me"), and modern remake of the classic *Pygmalion* story have made it a timeless entity in pop culture. [cite: 19 (from step 2), 25 (from step 2)]

The recent rush of reunions and new projects among the cast members—from Freddie Prinze Jr.'s horror comeback to Matthew Lillard's resurgence in the *Five Nights at Freddy's* universe—highlights the deep talent pool that defined the 1999 classic. Fans can look forward to seeing the beloved cast members continue to dominate screens, proving that the stars of the ultimate teen romantic comedy are, truly, all that.

actors in she's all that
actors in she's all that

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