25 years of Cruel Intentions: Where's the cast now?

In 1999, Cruel Intentions made its theatrical debut, captivating audiences with its portrayal of teen prep school culture and the seductive, sometimes perilous, dynamics among its characters. The film played a significant role in elevating the careers of its leads, including Reese Witherspoon, Selma Blair, and Sarah Michelle Gellar, and has continued to be a cultural reference point since its release.

Here, as the movie celebrates its 25th anniversary, take a look at the cast.

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Reese Witherspoon

Reese Witherspoon's career has flourished since her portrayal of Annette Hargrove, the headmaster's daughter, in Cruel Intentions. In the film, she is seduced by playboy Sebastian, portrayed by Witherspoon's real-life future (now ex) husband, Ryan Phillippe. Witherspoon has received acclaim and numerous award nominations and wins for her roles in films such as Legally Blonde, Sweet Home Alabama, and Walk the Line (2005), for which she won the Best Actress Oscar.

Sarah Michelle Gellar

During her time filming the popular series Buffy the Vampire Slayer, Sarah Michelle Gellar also appeared in several films, including "I Know What You Did Last Summer" and Scream 2, in addition to Cruel Intentions, where she portrayed the wealthy, popular, and devious Kathryn. Gellar is married to fellow actor Freddie Prinze Jr., whom she met on the set of I Know What You Did Last Summer. The couple exchanged vows in 2002 and have two children together, Charlotte Grace and Rocky James.

Ryan Phillippe

Ryan Phillippe captivated teens worldwide with his portrayal of the bad boy Sebastian. Throughout the 2000s, Phillippe maintained a prominent presence on the big screen, starring in films such as Way of the Gun, Crash, Flags of Our Fathers, and The Lincoln Lawyer. Additionally, he enjoyed a steady television career with roles in shows like Damages, Shooter, and Big Sky.

Selma Blair

After the film, Blair, alongside Witherspoon, starred in the 2001 comedy Legally Blonde. She also appeared in several movies during the early 2000s, including The Sweetest Thing, Hellboy, and Hellboy II: The Golden Army. Blair had television roles on Anger Management and portrayed Kris Jenner on American Crime Story: The People v. O.J. Simpson. In 2018, Blair disclosed that she had been diagnosed with multiple sclerosis.

Joshua Jackson

While Jackson's role in the film was minor, his career skyrocketed as Pacey Witter on the hit teen series Dawson's Creek. The Canadian actor has also landed leading roles on shows like Fringe, The Affair, Little Fires Everywhere, and Dr. Death. Jackson recently starred in the Paramount+ series Fatal Attraction, which premiered in April 2023, and is set to appear in the new Karate Kid film slated for release at the end of 2024.

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