The Stars of 'She's All That': Where Are They Now?

3:06 PM 1/29/2019

by Abbey White

The Freddie Prinze, Jr. and Rachael Leigh Cook romantic comedy turns 20 this year.

Teen romantic comedy She’s All That, which opened in theaters on Jan. 29, 1999, stars Freddie Prinze, Jr. and Rachael Leigh Cook as two seniors at a Southern California high school whose lives become entwined over a prom bet. 

After being abruptly dumped by his girlfriend for a reality TV star, class president and football team captain Zack (Prinze, Jr.) bitterly bets he can make any girl popular enough to beat his ex in her run for prom queen. That girl becomes Laney (Cook), a socially outcasted art student who after getting a Cinderella-esque makeover finds herself tangled in a world of popularity politics and romance.

Directed by Robert Iscove, the film grossed more than $103 million worldwide and helped inspire the teen drama parody Not Another Teen Movie. The cast is full of recognizable faces beyond its leading duo, including Paul Walker, Gabrielle Union, Usher, Tamara Mello and Elden Henson, who recently appeared in Daredevil.

To celebrate She's All That's 20th anniversary, The Hollywood Reporter takes a look at what the film’s stars have done since.

  • Rachael Leigh Cook (Laney Boggs)

    Miramax/Photofest; Jerod Harris/Getty Images

    Cook starred as Laney Boggs, a quirky, socially conscious outcast that becomes the focus of a prom queen bet between made by her eventual romantic interest, Zack. Initially reluctant to let the football team captain and the rest of his in-crowd into her life, Laney's walls slowly come down amid a makeover but re-emerge as she's increasingly used as a pawn by Zack and his friends. After She's All That, Cook starred in Josie and the Pussycats, Nancy Drew, Tangled, The Lodger, The Big Empty and A Midsummer Night's Dream. Cook also starred in Steven Spielberg's acclaimed Into the West miniseries and appeared on Dawson's Creek, Las Vegas, Ghost Whisperer, Perception, The Outer Limits and Psych. Cook is set to appear next in the romantic drama Valentine in the Vineyard, the third installment of a Hallmark movie series about two people who unexpectedly become joint owners of a vineyard.
     

  • Freddie Prinze, Jr. (Zachary "Zack" Siler)

    Miramax/Courtesy Everett Collection; Donna Ward/Getty Images

    After his girlfriend Taylor returns from summer break with a new beau, Zack officially becomes his school's most popular and eligible student. Nursing a wounded ego, Zack makes a bet that he can turn any girl at school into a prom queen who can beat Taylor. But after a friend selects outcast Laney as the makeover project, an initially reluctant Zack starts to see really both Laney and himself for the first time. Following his appearance in She's All That, Prinze Jr. continued to do romantic comedies, including Down to You, Boys and Girls, Head Over Heels, Summer Catch and Jack and Jill vs. the World. In 2002 he starred as Fred Jones in Warner Bros' live-action Scooby-Doo movie, as well as its 2004 follow-up Scooby-Doo 2: Monsters Unleashed. The actor has also had roles in the television series 24, Freddie, Boston Legal, Psych, Frasier, Friends, Witches of East End and Bones and did voice work for Happily N'ever After, Robot Chicken and Star Wars Rebels. The actor has made several appearances on WWE in addition to working as part of the WWE creative team.
     

  • Paul Walker (Dean Sampson, Jr.)

    Miramax/Courtesy Everett Collection; WireImage

    Dean is Zack's cocky, bro-ish friend who is often jealous of the football team captain and class president. He selects Laney as the girl Zack has to make over and bets against Laney taking Taylor's prom queen title. When he realizes Laney may have a chance, he attempts to sabotage Zack's plans. Following his role in She's All That, Walker went on to star in a variety of big-screen features, including Joy Ride, Into the Blue, Eight Below, Flags of Our Fathers and Brick Mansions. His role as Brian O'Conner in Universal's The Fast and the Furious, a film inspired by a Vibe article about the world of illegal street racing, served as one of the defining parts of his film career. Walker appeared in six of the franchise's films. The 2015 installment, Furious 7, would be the actor's final role following his death on Nov. 30, 2013.
     

  • Jodi Lyn O'Keefe (Taylor Vaughan)

    Miramax/Courtesy Everett Collection; Ari Perilstein/Getty Images

    O'Keefe starred as Taylor, a narcissistic and socially ruthless high school queen bee who returns from summer break with a reality TV star boyfriend. Taylor strings Zack along and becomes Laney's nemesis in her quest to be crowned prom queen. Since then, O'Keefe has starred in horror films The Crow: Salvation, Whatever It Takes and Red Rover. The actress also starred in three seasons of Prison Break with appearances in comedies Dharma & Greg, George Lopez, The Big Bang Theory and Two and a Half Men as well as dramas Charmed, Lucifer, Lost, Boston Legal, Criminal Minds, CSI: NY and Castle. She most recently appeared as Lionel Davenport on BET's dance drama Hit the Floor and was featured on one episode of Legacies, returning as her Vampire Diaries character Jo Laughlin.
     

  • Matthew Lillard (Brock Hudson)

    Miramax/Courtesy Everett Collection; Matt Winkelmeyer/Getty Images

    Lillard plays Brock Hudson, Taylor's older boyfriend she met during her summer break before senior year. Hudson is Zack's worst nightmare, appearing at school and parties as a generally obnoxious, self-obsessed reminder of Taylor's emotional flakiness. Since starring as Zack's egotistical foil, Lillard has appeared in several other films alongside his She's All That co-star, including romantic comedies Summer Catch and both installments of Warner Bros' live-action Scooby-Doo movies, where he starred as Shaggy Rogers. The actor's other major film roles have included Thir13en Ghosts, Wicker Park and The Descendants, the latter of which won best motion picture drama at the Golden Globes. In addition to a now extensive career voicing Shaggy Rogers for animated Scooby-Doo films, Lillard has appeared on The Bridge, Twin Peaks, Bosch, Halt and Catch Fire and Good Girls.
     

  • Gabrielle Union (Katarina "Katie" Darlingson)

    Miramax/Courtesy Everett Collection; Leon Bennett/WireImage

    Union plays Katie, a popular student and one of Taylor's groupies, though she's less impressed by her friend's immature and destructive antics. She often calls Taylor out and openly sides with Laney. Keeping with the teen drama genre, Union found success post-She's All That with roles in 10 Things I Hate About You and Bring It On. Since then, she's done dramas like Welcome to Collinwood, Neo Ned, The Birth of A Nation, The Public and Breaking In. Union has also played the leading lady in romantic comedies The Honeymooners, Think Like A Man, Good Deeds and Top Five. More recently, the actress starred in four seasons of BET's drama Being Mary Jane. In 2010, Union ventured into fashion, launching Love & Blessings, a plus-size clothing line, and in 2017, published We're Going to Need More Wine: Stories That Are Funny, Complicated, and True.
     

  • Dule Hill (Preston)

    Miramax/Courtesy Everett Collection; Leon Bennett/Getty Images

    Preston is a member of his high school's popular crowd and a charismatic, laid-back friend. He eggs on the bet between Zack and Dean but ultimately tires of the latter's competitive antics. Following a small role in 2003's Holes, Hill appeared as Charlie Young on The West Wing and as Burton Guster on USA Network's buddy-dramedy Psych — a role he reprised for the 2017 TV movie of the same name. Most recently he appeared in CBS' Doubt and on two seasons of HBO's Ballers. After appearing in a recurring role for season seven of Suits, Hill returned as a series regular in the latest and eighth season of the USA Network legal drama.
     

  • Kieran Culkin (Simon Boggs)

    Miramax/Courtesy Everett Collection; Amanda Edwards/WireImage

    Simon is Laney's somewhat oddball and supportive younger brother who looks up to Zack. Since playing the youngest member of the Boggs family, Culkin has appeared in The Cider House Rules, Scott Pilgrim v. The World, Margaret, Paperman and Igby Goes Down, the latter of which earned the actor a best young actor/actress Critics' Choice award. Culkin voiced a character for Cartoon Network's Long Live the Royals miniseries in addition to an appearance in FX's Fargo. Culkin is currently starring in the HBO drama Succession, a role that earned him a best supporting actor Golden Globe nomination.

     

  • Anna Paquin (Mackenzie "Mac" Siler)

    Miramax/Photofest; John Shearer/Getty Images

    Mac is a dry-witted and somewhat rebellious teen who readily offers her opinions on her older brother Zack's dilemmas. She is called on to help give Laney a makeover. Since then, Paquin has appeared in indie dramas Almost Famous and Squid and the Whale, as well as Fox's X-Men franchise. On TV, the actress is most famous for her leading role in HBO's romantic vampire drama True Blood, for which Paquin won a best actress Golden Globe. Paquin has also appeared in Bellevue, Alias Grace and The Affair. Up next, Paquin will star alongside Robert De Niro and Al Pacino in Martin Scorsese's The Irishman and in Pop TV's Flack as a publicist who can stop her clients' lives from crumbling, but not her own.

  • Kevin Pollak (Wayne Boggs)

    Miramax/Courtesy Everett Collection; Michael Kovac/Getty Images

    Wayne is Laney's gruff, well-meaning working-class father who, despite being socially out of touch, often serves as a voice of wisdom. Since his role in the 1999 teen rom-com, Pollak has appeared in The Front Runner, The Whole Nine Yards, The Wedding Planner, The Santa Clause 2 and The Santa Clause 3. He also directed Misery Loves Comedy, a documentary featuring more than 50 comedians, including Judd Apatow, Jimmy Fallon, Whoopi Goldberg and Lisa Kudrow. Pollak has appeared in Men at Work, Law & Order: SVU, Mom, Drunk History, House of Lies and The Good Fight. He can currently be seen in Amazon's The Marvelous Mrs. Maisel and is set to appear in a handful of films, including Apparition and Benjamin.
     

  • Clea DuVall (Misty)

    Ronald Grant/Everett Collection; Frederick M. Brown/Getty Images

    As Misty, DuVall plays an affluent art classmate of Laney's who bullied her before becoming a canvas for Laney's artistic revenge. Since then, DuVall has starred in genre thrillers The Grudge, The Astronaut's Wife and Passengers as well as dramas Girl, Interrupted and Argo. On the small screen, she's appeared in The Romanoffs, The Handmaid's Tale, Better Call Saul and The Newsroom, with more significant roles in Veep, The Lizzie Borden Chronicles, American Horror Story, Heroes and Carnivale. In 2016, DuVall made her feature directorial debut with The Intervention, which she also wrote.

     

  • Usher (Campus DJ)

    Miramax/Courtesy Everett Collection; Randy Shropshire/Getty Images

    Usher played the school's campus deejay, delivering the morning announcements and controlling the soundtrack for functions at the Southern California school. Since She's All That, Usher has released six albums and won eight Grammys. In addition to stints as a judge on talent reality competitions like The X Factor and The Voice, Usher has starred in films Texas Ranger and the Edgar Ramirez- and Robert De Niro-led boxing drama Hands of Stone. Other film appearances include Muppets Most Wanted and Scary Movie 5, as well as a handful of TV roles on teen shows like The Twilight Zone, Moesha, 7th Heaven and Sabrina, the Teenage Witch. Usher also served as a producer for two of Justin Bieber documentaries, Justin Bieber: Never Say Never and Justin Bieber's Believe.

  • Lil' Kim (Alex Chason Sawyer)

    Miramax/Courtesy Everett Collection; Johnny Nunez/WireImage

    Alex, played by Lil' Kim, was a member of Taylor's inner circle who stayed neutral and nicer when it came to the popular group's squabbles over Laney. Since appearing in She's All That, Lil' Kim has had roles in Zoolander, You Got Served and Superhero Movie. She has also appeared in guest roles on Moesha and The Game. Since 1999, Lil' Kim has released three studio albums and four mixtapes. In 2009 she competed on Dancing with the Stars and can be seen in the 2017 documentary Can't Stop, Won't Stop: A Bad Boy Story.