THEN AND NOW: The cast of ‘She’s All That’ 21 years later

Rachael Leigh Cook and Freddie Prinze Jr. in ‘She’s All That.’ Miramax
  • The rom-com “She’s All That” was released in January 1999, starring Rachael Leigh Cook and Freddie Prinze Jr. as love interests.
  • Since the movie came out, Cook has continued to star in movies and shows, like the 2020 rom-com “Love, Guaranteed.”
  • Prinze Jr. still acts, but he’s also a cookbook author.
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“She’s All That” was released in theatres in January 1999 and became an instant classic teen rom-com.

The film, which was loosely based on the George Bernard Shaw’s play titled “Pygmalion” and the 1964 movie “My Fair Lady,” focused on a high school student named Zack, who made a bet with his friend that he could transform any girl at William Henry Harrison High School into a prom queen.

The cast of “She’s All That” was comprised of plenty of actors who went on to become notable names in Hollywood, including Rachael Leigh Cook, Freddie Prinze Jr., and Paul Walker.

There’s also a gender-swapped remake in the works starring TikTok influencer Addison Rae.

Here’s what the stars have been up to since the movie came out on January 29, 1999.

Rachael Leigh Cook starred as Laney Boggs, a clumsy student who was passionate about art.

Rachael Leigh Cook as Laney Boggs in ‘She’s All That.’ Miramax

She wasn’t concerned with being a popular student at school.

Cook has since starred in even more movies and TV shows.

Rachael Leigh Cook in August 2019. Willy Sanjuan/Invision/AP

Cook won the MTV Movie and TV Award for best breakthrough female performance for her role in “She’s All That.”

Afterward, she guest-starred on “Dawson’s Creek” in 1999, and starred as Clara in the 2005 miniseries “Into the West.” Cook’s other TV credits include parts on “Psych,” “Perception,” and “Robot Chicken.”

Cook also had a cameo in singer Khalid’s music video for “Young Dumb & Broke.”

In 2020, she produced and starred in the rom-com “Love, Guaranteed.”

The actress married “The Originals” star Daniel Gillies in 2004 and split in 2019. The stars have two children together, a daughter named Charlotte and a son, Theodore.

Freddie Prinze Jr. starred as the school’s jock and class president, Zack Siler.

Freddie Prinze Jr. as Zack Siler in ‘She’s All That.’ Miramax

He had the fourth-highest GPA in his class and was determined to turn Laney into a prom queen within six weeks because he couldn’t stand the idea of losing a bet.

Freddie Prinze Jr. continues to act, but he’s also a cookbook author.

Freddie Prinze Jr. in 2016. Donna Ward/Getty Images

After “She’s All That,” Prinze Jr. landed roles in movies like “Head Over Heels” and “Summer Catch.” He also guest-starred on “Friends.”

The actor shared the screen with Sarah Michelle Gellar, who he married in 2002. The couple costarred as Fred and Daphne in the live-action “Scooby-Doo” movies, and Gellar even appeared during a cafeteria scene in “She’s All That.”

Prinze Jr. and Gellar have two children together and have turned their passion for food into books. In 2016, Prinze Jr. released “Back to the Kitchen: 75 Delicious, Real Recipes (& True Stories) from a Food-Obsessed Actor,” which included a foreword from Gellar.

Zack’s friend, Dean Sampson, was portrayed by Paul Walker.

Paul Walker as Dean Sampson in ‘She’s All That.’ Miramax

Dean is the one who challenged Zack to give Laney a makeover. He later took her to prom and showered her in compliments in an attempt to get her to sleep with him.

Paul Walker starred as Brian O’Conner in the “Fast and Furious” franchise until his death in November 2013.

Paul Walker at the world premiere of ‘Fast and Furious 6,’ in 2013. Joel Ryan/Invision/AP

Walker died in a car crash at the age of 40, while on his way to a charity event. At the time, he was still in the middle of filming the seventh “Fast and Furious” movie, so Walker’s brothers stepped in to help the cast and crew complete any remaining scenes that the star was involved in.

When “Furious 7” hit theatres in 2015, it featured the Wiz Khalifa and Charlie Puth song “See You Again,” which was included as a tribute to Walker. The emotional track also got nominated for three Grammys.

Walker is survived by his daughter, Meadow Rain.

Jodi Lyn O’Keefe played Taylor Vaughan, the school’s resident popular girl.

Jodi Lyn O’Keefe as Taylor Vaughan in ‘She’s All That.’ Miramax

Taylor and Zack were a power couple, but she abruptly broke up with him after spending spring break in Daytona, Florida, and cheating on him with a new guy named Brock.

Fans of “The Vampire Diaries” will recognise O’Keefe for her role as Jo Laughlin on the hit CW series.

Jodi Lyn O’Keefe in June 2018. (Photo by Willy Sanjuan/Invision/AP

O’Keefe had roles on other popular series, including “Prison Break” and “Two and a Half Men.” She also guest-starred on the original “Charmed” in 2004.

More recently, she portrayed Lionel Davenport on the drama series “Hit the Floor.”

Acting aside, she released her own jewellery line and clothing collection.

Matthew Lillard starred as Brock Hudson, a narcissist and local celebrity thanks to his role on the reality TV show “Real World.”

Matthew Lillard as Brock Hudson in ‘She’s All That.’ Miramax

Brock loved watching the episodes that he was featured on, and even got a tattoo of his face on his arm. His relationship with Taylor was short-lived and he ended up breaking up with her.

Over the years, Lillard has voiced Shaggy in several “Scooby-Doo” movies and TV series.

Matthew Lillard in January 2020. Paul Archuleta/FilmMagic

In addition to reuniting with Prinze Jr. for two “Scooby-Doo” movies (in 2002 and 2004), he played Dean Boland on the NBC comedy “Good Girls” and William Hastings on “Twin Peaks.”

Lillard has been married to Heather Helm since 2000 and they have three children together.

Anna Paquin starred as Zack’s younger sister, Mackenzie Siler.

Anna Paquin as Mackenzie Siler in ‘She’s All That.’ Miramax

Mackenize tweezed Laney’s eyebrows and gave her a new, shorter hairstyle.

Paquin is now known for her role as Sookie Stackhouse on HBO’s “True Blood.”

Anna Paquin in January 2020. Jordan Strauss/Invision/AP

In addition to her Golden Globe-nominated role on the vampire series, Paquin went on to play Rogue in the “X-Men” movies.

In real life, she’s married to “True Blood” costar Stephen Moyer and they have fraternal twins named Charlie and Poppy.

Paquin is also an advocate for the LGBTQIA community since coming out as bisexual in 2010.

Paquin recently appeared on shows like “The Affair” and “Flack.” She also had a supporting role in the Oscar-nominated movie “The Irishman.”

Laney’s little brother, Simon Boggs, was played by Kieran Culkin.

Kieran Culkin as Simon Boggs in ‘She’s All That.’ Miramax

Simon was a stereotypical, annoying younger brother. Zack also stood up for him at one point after he got bullied at school.

Kieran Culkin currently stars on the hit HBO drama “Succession.”

Kieran Culkin in January 2020. Willy Sanjuan/Invision/AP

His role as Roman Roy on the series earned Culkin two Golden Globe nominations (in 2019 and 2020) for best performance by an actor in a supporting role in a limited series or motion picture made for television.

Outside of his participation on TV shows, the 38-year-old was part of several theatre productions in New York.

He also enjoys trolling his brother, Macaulay Culkin, online and has been married to Jazz Charton since 2013. Culkin and his wife welcomed their first child, a daughter named Kinsey Sioux, in September 2019.

Laney’s loyal childhood friend, Jesse Jackson, was portrayed by Elden Henson.

Elden Henson as Jesse Jackson in ‘She’s All That.’ Miramax

Jesse always looked out for Laney and couldn’t resist eating Twinkies, despite saying that he’d lose 10 pounds before graduation.

Henson most recently appeared as Foggy Nelson, the best friend of Matt Murdock, on “Daredevil.”

Elden Henson played Pollux in the ‘Hunger Games’ franchise. Dimitrios Kambouris/Getty Images for IMDb

Henson also guest-starred on “Grey’s Anatomy,” “Workaholics,” “Private Practice,” and “Psych.”

Usher Raymond played the school’s DJ.

Usher Raymond in ‘She’s All That.’ Miramax

He was responsible for giving the morning announcements and was the DJ at the senior prom, which featured an iconic choreographed dance scene.

Usher went on to become a Grammy-winning singer.

Usher in August 2018. Gabe Ginsberg/FilmMagic

Since the ’90s, he’s released more than five studio albums, which have sold millions of copies worldwide. His chart-topping songs include “Yeah!” “Burn,” and “OMG.”

He also had a cameo in 2019’s “Hustlers,” which starred Jennifer Lopez.

Usher was previously married to Tameka Foster and they have two sons together. He later wed Grace Miguel, but the pair split in 2018 after two years of marriage. He welcomed a daughter named Sovereign Bo Raymond with girlfriend Jenn Goicoechea in September 2020.

Gabrielle Union starred as Katie, one of Taylor’s closest friends.

Gabrielle Union as Katie in ‘She’s All That.’ Miramax

Katie nominated Laney for prom queen.

Gabrielle Union has starred in plenty of rom-coms since “She’s All That.”

Gabrielle Union in May 2019. Willy Sanjuan/Invision/AP

Union starred in the 2000 movie “Bring It On.”

She landed roles in “Deliver Us From Eva” with LL Cool J, “Breakin’ All the Rules” with Jamie Foxx, and “Think Like a Man” with Taraji P. Henson.

The 47-year-old has also been praised for her role as the titular character on the series “Being Mary Jane.”

Union has been married to NBA star Dwyane Wade since 2014 and the couple welcomed a daughter named Kaavia James Union Wade via surrogate in late 2018.

The actress currently stars as Sydney Burnett on the show “L.A.’s Finest” alongside Jessica Alba.

Dulé Hill played another one of Zack’s friends, named Preston.

Dulé Hill as Preston in ‘She’s All That.’ Miramax

He lived in a huge house, which was perfect for throwing high school parties.

Hill starred on the Showtime series “Black Monday.”

Dulé Hill in October 2018. Leon Bennett/Getty Images

Prior to that, he had successful runs on other series, including “The West Wing,” “Ballers,” “Suits,” and “Psych.”