'She's All That' : See the Cast of the Teen Classic Then and Now

Take a look back at the cast of the classic 1999 teen rom-com and their transformations

01 of 14

A She's All That Reunion

Freddie Prinze Jr. and Rachael Leigh Cook attend the ''Christmas With You'' special screening at The Bay Theater on November 08, 2022 in Pacific Palisades, California.
Charley Gallay/Getty

Nineties kids melted for a moment in November when She's All That stars Freddie Prinze Jr. and Rachel Leigh Cook reunited at the premiere of Prinze's new Netflix project, Christmas with You, in L.A.

"What a great night, so happy for you my friend!" Cook wrote in an Instagram caption. "SO GOOD ⭐️⭐️⭐️⭐️⭐️"

So where have the stars of the film been since it hit theaters in 1999? Read on!

02 of 14

Rachael Leigh Cook as Laney Boggs

Miramax/Kobal/REX/Shutterstock; Rachel Luna/Getty

She's All That was unquestionably the kick-off to Rachel Leigh Cook's career. Since her days as dorky Laney, she's gone on to appear in many different shows, several of which involved voice roles such as Robot Chicken. She also starred in several Hallmark Channel films, and, in 2017, made a cameo in Khalid's "Young, Dumb and Broke" music video. In 2021, she appeared in the gender-swapped remake of the film — He's All That — this time as the mom of the teenage girl who is giving (not getting) the makeover.

She has two kids with ex-husband and actor Daniel Gillies, whom she married in 2014. The couple split in 2019 and finalized their divorce in 2021.

03 of 14

Freddie Prinze Jr. as Zack Siler

Claudette Barius/Miramax/Kobal/REX/Shutterstock; Donna Ward/Getty

Other than his role as hot-shot Zack in the film, Freddie Prinze Jr. may be best known for portraying Fred in the Scooby-Doo film series. He starred in a short-lived 2005 sitcom about his own life, had a recurring role in 24 in 2010 and lent his voice to the Disney XD series Star Wars Rebels. In 2021, he appeared in the Peacock Punky Brewster reboot.

In 2002, Prinze married Sarah Michelle Gellar, who also appeared in the Scooby-Doo movies with him as Daphne — and had a small cameo in She's All That. They have two children.

04 of 14

Jodi Lyn O'Keefe as Taylor Vaughan

Moviestore/REX/Shutterstock; Ari Perilstein/Getty

Since playing Zack's mega-popular (and eventually, mega-dumped) ex-girlfriend, Jodi Lyn O'Keefe has appeared in a long list of different television shows, including Prison Break, The Vampire Diaries, the VH1 sports-drama series Hit The Floor and the 2021 television film Hip Hop Family Christmas.

05 of 14

Matthew Lillard as Brock Hudson

Miramax/Kobal/REX/Shutterstock; Kevin Winter/Getty

After his turn as the wild reality star who stole Zack's popular girlfriend, Matthew Lillard went on to star in the Scooby-Doo films with Prinze, as Shaggy. He continues to be involved as Shaggy, voicing many Scooby-Doo animated films. Lillard made his directorial debut with the 2012 drama Fat Kid Rules the World and has appeared in television series like the 2017 revival of Twin Peaks and NBC's Good Girls.

He is married with three children.

06 of 14

Gabrielle Union as Katie Darlingson

Roy Rochlin/Getty

Since making her big-screen debut as popular girl Katie in She's All That, Gabrielle Union has gone on to become one of the most famous faces in Hollywood. Her breakthrough role came in Bring It On in 2000, and since then she has landed many different film gigs. In the world of TV, she has starred in the series Being Mary Jane and L.A.'s Finest. On top of that, she is known for her strong activism, specifically as an advocate for sexual assault survivors and LGBTQ+ youth.

In late 2018, she welcome her first child, a daughter, with now-retired NBA star husband Dwyane Wade.

07 of 14

Dulé Hill as Preston

Dule Hill in She's All That
Claudette Barius/Miramax/Kobal/Shutterstock; David Livingston/Getty

After his turn as one of Zack's pals in She's All That, Dulé Hill went on to star on The West Wing for all seven seasons, followed by Psych, Doubt, Ballers, Black Monday and the 2021 revival of The Wonder Years.

He is married to actress Jazmyn Simon. They have two children.

08 of 14

Anna Paquin as Mackenzie Siler

Claudette Barius/Miramax/Kobal/REX/Shutterstock; Vivien Killilea/Getty

Since playing Zack's little sister, Oscar-winner Anna Paquin has had a strong career in TV and film. After appearing as mutant Rogue in the X-Men film series, she led the HBO hit True Blood. Her role as Sookie Stackhouse garnered her a Golden Globe Award for best actress in a television series – drama in 2009. She later starred on the Amazon series Flack.

She is married to actor (and her True Blood costar) Stephen Moyer, and they have twins, Poppy and Charlie, born in 2012.

09 of 14

Kieran Culkin as Simon Boggs

Donato Sardella/Getty

Macaulay Culkin's little brother played Laney's little brother and eventually made a name for himself in Hollywood. In 2002, Kieran Culkin was nominated for a Golden Globe for his appearance in the film Igby Goes Down. He starred in season 2 of Fargo and is a standout as one of the Roy children on HBO's Succession. He has been nominated for multiple Golden Globes, Emmys and Screen Actors Guild Awards for his performance in the series.

10 of 14

Elden Henson as Jesse Jackson


Elden Henson — who played Laney's protective, encouraging friend Jesse — is best recognized for his role in the Marvel Cinematic Universe TV shows as Foggy Nelson, as well as appearances in the final two Hunger Games films as Pollux.

He was married from 2014 to 2016 but is divorced from his wife. They share one child.

11 of 14

Clea DuVall as Misty

Siemoneit/Sygma/Getty; Alberto E. Rodriguez/Getty

In the 20-plus years since playing mean art student Misty, Clea DuVall has made consistent appearances in both film and television. She landed roles in the acclaimed film Argo and appeared in television shows such as Heroes and The Lizzie Borden Chronicles, where she portrayed Emma Borden. She also had recurring roles on Veep and The Handmaid's Tale. In 2020, she co-wrote and directed the LGBTQ+ Hulu holiday rom-com, Happiest Season.

12 of 14

Kimberly 'Lil' Kim' Jones as Alex Sawyer

Miramax/Everett; Gabriel Olsen/FilmMagic

Now best known as her stage name Lil' Kim, Kimberly Jones' rap career has blown up since she appeared as one of the popular girls in She's All That. With millions of album copies sold, she is considered one of the greatest female rappers ever.

In 2005, she served a year-long prison sentence for lying to a federal grand jury. She has one child, a daughter named Royal Reign, born in 2014.

13 of 14

Usher as the School DJ

Usher in She's All That
Claudette Barius/Miramax/Kobal/Shutterstock; Getty

Already a household name, Usher played the resident high school DJ in the film. He's acted quite a bit since, though music has been his main focus. Since She's All That, he's continued to release singles and albums and served as a coach and advisor on The Voice.

In 2021, he welcomed his fourth child, which was his second child with girlfriend Jenn Goicoechea.

14 of 14

Paul Walker as Dean Sampson


Paul Walker was on a roll with teen movies — Pleasantville, Varsity Blues and The Skulls — when he took on the role of Zack's backstabbing pal Dean in She's All That. He went on to star in the Fast and the Furious franchise, in addition to other films.

Walker tragically died in a car accident in 2013. He is survived by a daughter, Meadow.

Related Articles