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Then + Now: The Cast of ‘She’s All That’

she's all that
Miramax

In keeping with the ’90s trend of turning classic literature into MTV-friendly teen rom coms, ‘She’s All That’ is a modern-day adaptation of the George Bernard Shaw play ‘Pygmalion,’ set in a high school.

In the film, a popular jock accepts a bet to turn a nerdy loner into the prom queen. That plot and its young cast must have appealed to audiences, because ‘She’s All That’ became the highest grossing teen romance movie to date.

See what the actors and actresses of ‘She’s All That’ are up to today.

Freddie Prinze, Jr. (Zach Siler)

freddie prinze
YouTube/Frederick M. Brown, Getty Images

Then: In ‘She’s All That,’ Prinze, Jr. plays big man on campus Zach Siler, who takes a bet that he can’t make a geeky girl into the prom queen. The son of the late actor and comedian Freddie Prinze, Prinze, Jr. was known at the time for starring in the ‘I Know What You Did Last Summer’ franchise.

Now: His last big role was as Cole Ortiz on the final season of ‘24.’ He has been married to actress Sarah Michelle Geller — whom he met filming ‘I Know What You Did Last Summer’ — since 2002, and they have two children.

Rachael Leigh Cook (Laney Boggs)

rachael cook
YouTube/Valerie Macon, Getty Images

Then: Cook entered the big leagues as Laney Boggs, the geeky girl who only needed to take off her glasses to be prom queen material. Cook started print modeling as a child and made her film debut at the age of 15 in ‘The Baby-Sitters Club.’

Now: She currently stars on the procedural drama ‘Perception.’ She will be the lead in the upcoming movie ‘Red Sky.’

Paul Walker (Dean Sampson)

paul walker
YouTube/Kevork Djansezian, Getty Images

Then: Walker played Zach’s two-faced best buddy Dean Sampson in ‘She’s All That.’ Earlier that year, he had gotten his big break as injured quarterback Lance Harbor in ‘Varsity Blues.’

Now: Not long after ‘She’s All That,’ Walker took his all-American looks to the ‘The Fast and the Furious’ franchise, which he remains most famous for. Later in 2013, he’s slated to play the lead in ‘Hours,’ a movie about the aftermath of Hurricane Katrina.

Jodi Lyn O’Keefe (Taylor Vaughan)

jodi lynn
YouTube/John Sciulli, Getty Images

Then: O’Keefe made an impression as snobby popular girl Taylor Vaughan, who dumped Zach for a fading reality TV star and set the plot in motion. The former model, then 20, was in the middle of her run as Cassidy Bridges on ‘Nash Bridges’ and had made her acting debut four years earlier on the daytime soap ‘Another World.’

Now: Since playing series regular Gretchen Morgan on ‘Prison Break,’ O’Keefe has popped up on ‘Two and a Half Men,’ ‘Castle,’ ‘Lost’ and ‘Law and Order: LA.’ She also owns the fashion line Queen George Clothing.

Matthew Lillard (Brock Hudson)

matthew lillard
YouTube/Jason Merritt, Getty Images

Then: Lillard played obnoxious former reality TV star Brock Hudson in ‘She‘s All That.’ (The role was reportedly based on notorious ‘The Real World: San Francisco’ troublemaker Puck.) Then 28, Lillard had appeared in ‘Scream’ and ‘Scream 2’ and had garnered critical acclaim for his leading role in the indie film ‘SLC Punk.’

Now: Since starring as Shaggy in 2002’s live-action ‘Scooby Doo,’ Lillard has become the go-to voice for the iconic slacker in his animated version. More recently, he showed his dramatic skills, playing supporting roles in movies such as ‘The Descendants’ and ‘The Trouble With The Curve.’

Anna Paquin (MacKenzie Siler)

anna paquin
YouTube/Jason Merritt, Getty Images

Then: Paquin played Zach’s fashion-obsessed little sister Mac. Canada-born and New Zealand-raised, Paquin burst on the scene six years earlier with an Oscar-winning performance in ‘The Piano.’

Now: Paquin is Sookie Stackhouse in the vampire drama ‘True Blood,’ and she recently starred in the dramedy ‘Straight A’s.’ The actress had twins with her husband and ‘True Blood’ co-star, Stephen Moyer.

Kieran Culkin (Simon Boggs)

kieran culkin
YouTube/Stephen Lovekin, Getty Images

Then: Culkin played Lacey’s younger brother Simon in ’She’s All That.’ He got his Hollywood start as a 7-year-old as one of the McCallister kids alongside his brother Macaulay in ’Home Alone.’

Now: After well-received turns in a pair of 2002 films, ’The Dangerous Lives of Altar Boys’ and ’Igby Goes Down,’ Culkin seemed headed toward movie stardom. Instead, he took a six-year break from films and concentrated on theatre. He has since returned to the big screen, and his more recent credits include ‘Scott Pilgrim vs. The World’ and ‘Margaret.’

Elden Henson (Jesse Jackson)

Elden
YouTube/Wonder Entertainment

Then: You might remember Henson as Jesse Jackson, Laney’s nerdy friend in ’She’s All That.’ As Elden Ratliff, Henson had played enforcer Fulton Reed in the ‘Mighty Ducks’ trilogy.

Now: Henson has had guest roles on shows like ‘Psych,’ ‘Private Practice’ and ‘Grey’s Anatomy.’ He also played a supporting character in the Steve Jobs biopic ‘Jobs.’

Dulé Hill (Preston)

dule hill
YouTube/Frazer Harrison, Getty Images

Then: Hill was Preston, the most level-headed of Zach’s friends. Previously he had popped up on shows like ‘Cosby’ and ‘New York Undercover.’

Now: A TV mainstay, Hill played presidential aide Charlie Young for seven seasons on ‘The West Wing.’ Since that show ended, he’s been P.I. Gus Guster on the comedy-drama ‘Psych.’

Gabrielle Union (Katie Darlingson)

gabrielle union
YouTube/D Dipasupil, Getty Images

Then: Union played good-hearted popular girl Katie in ‘She’s All That.’ The next year, she snagged her biggest role to date as a competitive cheerleader in ‘Bring It On.’

Now: She starred in the movies ‘Think Like a Man’ and ‘Good Deeds.’ She is dating basketball star Dwayne Wade, who is 10 years her junior.

Next: See the Cast of 'Dumb and Dumber' Then and Now

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