25 Years Later: Where The Cast Of 'She's All That' Is Now—Including A Shocking New Reunion Movie

The iconic 1999 teen rom-com *She's All That* captivated a generation, defining the high school movie genre with its classic 'nerd-to-queen' transformation trope. Released over two decades ago, the film, which celebrated its 25th anniversary in January 2024, launched the careers of some of the biggest names in Hollywood, creating a cultural touchstone that remains beloved today. The question on every fan's mind is: where are the students of Fairmount High now, and what have they been up to since the famous "Am I original?" dance scene?

The good news for fans is that the stars are more active than ever, with many major new projects in 2024 and 2025, including a highly anticipated reunion between the film's two leads. From Oscar nominations and major Netflix deals to a new holiday movie, the cast has certainly not slowed down. Here is the definitive, up-to-date look at the main cast of *She's All That* and their current careers.

The Main Cast: Full Biography and Newest Projects (2024-2025)

Freddie Prinze Jr. as Zack Siler

Freddie Prinze Jr. played the popular, confident, and slightly arrogant jock, Zack Siler, who makes a bet that he can turn the school's outcast into the Prom Queen. Prinze Jr. was the quintessential teen heartthrob of the late 90s and early 2000s, cementing his status with roles in *I Know What You Did Last Summer* and *Summer Catch*.

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• Full Name: Freddie James Prinze Jr.
• Born: March 8, 1976 (Age 48 as of late 2024)
• Role in Film: Zack Siler, the popular student who takes on the challenge to transform Laney Boggs.
• Spouse: Sarah Michelle Gellar (married since 2002)
• Notable Post-1999 Roles: *Scooby-Doo* (2002), *24* (2010), voice work in *Star Wars Rebels* (2014–2018).
• FRESH UPDATE (2024-2025): Prinze Jr. is set to reunite with his co-star Rachael Leigh Cook in the upcoming holiday romantic comedy, *The Christmas Affair*. This marks their first on-screen reunion since *She's All That*, generating significant buzz among nostalgic fans. He also appeared at the 2024 90s Con for a reunion panel.

Rachael Leigh Cook as Laney Boggs

Rachael Leigh Cook starred as Laney Boggs, the artistic, glasses-wearing outcast who is the subject of Zack's bet. Her transformation scene, set to Sixpence None The Richer's "Kiss Me," is one of the most memorable moments in teen movie history. Cook has maintained a steady career in film and television, often starring in romantic comedies.

• Full Name: Rachael Leigh Cook
• Born: October 4, 1979 (Age 45 as of late 2024)
• Role in Film: Laney Boggs, the talented art student who becomes the object of the bet.
• Notable Post-1999 Roles: *Josie and the Pussycats* (2001), *Perception* (TV series, 2012–2015), and numerous Hallmark and Netflix holiday films like *Love, Guaranteed* (2020) and *Rescuing Christmas* (2024).
• FRESH UPDATE (2024-2025): The biggest news is her highly anticipated reunion with Freddie Prinze Jr. in the new holiday film, *The Christmas Affair*. She has also been promoting her 2024 film *Rescuing Christmas* and participated in the 25th-anniversary celebrations.

Matthew Lillard as Brock Hudson

Matthew Lillard played Brock Hudson, the obnoxious reality TV star and former boyfriend of Taylor Vaughan. Lillard’s over-the-top performance was a comedic highlight, and he is perhaps best known for his roles in *Scream* and as Shaggy in the live-action *Scooby-Doo* films.

• Full Name: Matthew Lyn Lillard
• Born: January 24, 1970 (Age 54 as of late 2024)
• Role in Film: Brock Hudson, the self-obsessed reality TV star.
• Notable Post-1999 Roles: Shaggy Rogers in the *Scooby-Doo* franchise, *The Descendants* (2011), and Dean Boland in the TV series *Good Girls* (2018–2021).
• FRESH UPDATE (2024-2025): Lillard continues his iconic association with the *Scooby-Doo* franchise, with reports indicating he is in talks to reprise his role as Shaggy for a new live-action Netflix series. He also starred in the 2024 Stephen King adaptation, *The Life of Chuck*, which won an award at the Toronto Film Festival.

Paul Walker as Dean Sampson

Paul Walker played Dean Sampson, Zack's friend who initiates the infamous bet. Walker's career skyrocketed shortly after *She's All That* with his role in *The Fast and the Furious* franchise. Tragically, Walker passed away in a car accident in 2013.

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• Full Name: Paul William Walker IV
• Born: September 12, 1973
• Died: November 30, 2013 (Age 40)
• Role in Film: Dean Sampson, the co-conspirator of the bet.
• Legacy: Walker's enduring legacy is his role as Brian O'Conner in the billion-dollar *Fast & Furious* series, which continues to honor his memory. His daughter, Meadow Walker, has continued his philanthropic work through The Paul Walker Foundation.

More Iconic Cast Members: From Oscar Winners to Succession Stars

The star power of *She's All That* extended far beyond the two leads, featuring a stunning ensemble cast of actors who went on to achieve massive success in subsequent years. The film is often cited for its incredible collection of future A-listers in smaller roles.

Kieran Culkin as Simon Boggs

Kieran Culkin, the younger brother of Macaulay Culkin, played Laney Boggs' eccentric younger brother, Simon. His role was small but memorable, often serving as the voice of reason for his sister.

The Culkin Comeback: Kieran Culkin’s career reached new heights with his critically acclaimed role as Roman Roy in the HBO series *Succession*, for which he won an Emmy Award in 2024. In the film world, he starred in the 2024 comedy-drama *A Real Pain*, which received rave reviews at the Sundance Film Festival. He also continues his voice work in the animated series *Solar Opposites* through 2025.

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Anna Paquin as Mackenzie Siler

Anna Paquin played Mackenzie Siler, Zack’s cynical and supportive younger sister. Paquin was already an Academy Award winner for *The Piano* (1993) when she took on the role in *She's All That*.

Oscar Winner to Power Producer: Following the film, Paquin starred as Rogue in the *X-Men* movie franchise and won a Golden Globe for her lead role as Sookie Stackhouse in the HBO hit series *True Blood*. In 2024, Paquin headlined the drama film *A Bit of Light*, which was directed by her husband, Stephen Moyer, showcasing her continued involvement in both acting and producing.

Gabrielle Union as Katarina "Katie" Darlingson

Gabrielle Union played Katarina "Katie" Darlingson, one of Taylor Vaughan's friends. Union's career exploded shortly after, particularly in the teen movie genre with *Bring It On* (2000).

From Cheerleader to Mogul: Union has become a powerhouse actress, author, and producer. In 2024, she was a producer on the hit romantic comedy *The Idea of You*. She is also set to star in the upcoming action-comedy film *Riff Raff*. Beyond acting, Union and her husband, Dwyane Wade, are scheduled to star in a new HGTV home renovation show.

Jodi Lyn O'Keefe as Taylor Vaughan

Jodi Lyn O'Keefe played Taylor Vaughan, the mean-spirited, popular girl whose breakup with Zack starts the whole bet. Her character is the quintessential 90s high school villain.

Continuing the Drama: O'Keefe has maintained a strong presence in television drama. She is widely recognized for her roles as Gretchen Morgan on *Prison Break* and as Jo Laughlin on *The Vampire Diaries*. Her recent work includes appearances in various television movies and guest spots, keeping her busy in the industry.

The Legacy and Topical Authority of She's All That

The enduring popularity of *She's All That* is a testament to its perfect capture of 90s culture and its timeless themes of authenticity and self-discovery. The film's 25th anniversary in 2024 brought a renewed focus on its impact, with the main cast participating in various reunion events.

The movie's topical authority was further cemented by the 2021 gender-swapped remake, *He's All That*, which starred Addison Rae and featured Rachael Leigh Cook in a new role as the mother of the main character. This move demonstrated the original film's lasting influence and its ability to be successfully reinterpreted for a new generation.

However, the most exciting development is the upcoming holiday film, *The Christmas Affair*, which promises to deliver the on-screen chemistry fans have missed for a quarter-century. This project is a direct nod to the film's legacy and a gift to fans who grew up watching Zack Siler and Laney Boggs fall in love. The fact that the cast members continue to headline major projects—from Oscar-buzz films to hit streaming shows—proves that the class of Fairmount High is still very much at the top of Hollywood's A-list.