Summary

• Cruel Intentions is a stylish, successful movie with a talented cast and a clever script, earning over $75 million worldwide.
• The actors who starred in the film, such as Sarah Michelle Gellar, Ryan Phillippe, and Reese Witherspoon, went on to have successful careers in Hollywood.
• The film's impact is still felt today, with actors like Selma Blair and Joshua Jackson continuing to appear in films and TV shows, and even a television reboot in the works.

The seductive teen drama Cruel Intentions was released in 1999 with a cast full of actors who have since achieved varying degrees of fame in Hollywood. Cruel Intentions is a modern take on Les Liaisons dangereuses, a 1782 novel by Pierre Choderlos de Laclos. The film tells the story of Kathryn Merteuil (Sarah Michelle Gellar) and Sebastian Valmont (Ryan Phillipe), two wealthy step-siblings from the Upper East Side who make a wager: if Sebastian can bed Annette (Reese Witherspoon), daughter of the heaster at their school, Kathryn will sleep with him. If he can't, Kathryn gets Sebastian's vintage Jaguar. What begins as a game blossoms into a romance when Sebastian and Annette fall in love.

Cruel Intentions is a stylish movie that combines a stellar cast of actors and an edgy and witty script. The film was a box office success, earning over $75 million worldwide, with a budget of just $10.5 million. The success of the film resulted in two sequels, neither of which were well-received. But while the movie franchise wasn't able to last, the actors who made the film what it was continued to appear in movies and TV shows decades after its 1999 release.

Sarah Michelle Gellar (Kathryn Merteuil)

By the time Sarah Michelle Gellar landed the role of seductress Kathryn Merteuil, she had already starred in films such as I Know What You Did Last Summer and Scream 2. She was also two years into her leading role in the hit television series Buffy The Vampire Slayer. Following Cruel Intentions, Sarah Michelle Gellar turned down several movie roles, putting her focus on Buffy. She still made time for occasional films like Scooby Doo, The Grudge 2, and Suburban Girl. She has been married to Freddie Prinze Jr. for 21 years, and the couple share a son and a daughter. Gellar recently starred in the fantasy series Wolfpack.

Ryan Phillippe (Sebastian Valmont)

Ryan Phillippe portrays the cunning Sebastian Valmont in Cruel Intentions. This was Ryan Phillippe's second film with Sarah Michelle Gellar, having both starred in I Know What You Did Last Summer. Ryan Phillippe and Reese Witherspoon met on the set of Cruel Intentions and were married weeks after the film's release. The couple were divorced in 2008 and share two children. Phillippe went on to star in films such as Crash, Breach, and The Lincoln Lawyer. He also starred in television series such as Damages, Secrets and Lies, and Shooter. Ryan Phillippe's new film, Miranda's Victim, was released this month.

Reese Witherspoon (Annette Hargrove)

Reese Witherspoon continues to have an illustrious career following her role as Annette Hargrove, the Heaster's virgin daughter, whom Sebastian seduces. Following Cruel Intentions, Witherspoon starred in films such as Election, American Psycho, Legally Blonde, and Sweet Home Alabama. Her role as June Carter in 2005's Walk The Line earned her an Oscar for Best Actress. She has also had a successful television career, starring in Big Little Lies, Little Fires Everywhere, and The Morning Show, which is in its third season on Apple TV+.

Selma Blair (Cecile Caldwell)

Selma Blair portrays the naive Cecile Caldwell and shares a memorable kissing scene with Sarah Michelle Gellar. Following Cruel Intentions, Blair starred alongside Reese Witherspoon in Legally Blonde. She has since appeared in many other films, including The Sweetest Thing, A Guy Thing, and the Hellboy franchise. In 2016, Blair portrayed Kris Jenner in American Crime Story: The People v. O.J. Simpson. In 2018, Selma Blair announced that she was diagnosed with multiple sclerosis, and in 2021, she released a documentary titled Introducing, Selma Blair, which documented her battle with the disease.

Joshua Jackson (Blaine Tuttle)

Joshua Jackson stars as Blaine Tuttle, who assisted Sebastian in blackmailing Annette's ex-boyfriend. Joshua ed the cast of Cruel Intentions at the beginning of his successful television career. Jackson played Pacey Witter on the successful teen drama Dawson's Creek, which aired from 1998 to 2003. He starred in other TV shows as well, including Fringe, The Affair, Little Fires Everywhere (with Cruel Intentions costar Reese Witherspoon), and Dr. Death. Most recently, Jackson starred in Fatal Attraction opposite Lizzy Caplan on Paramount+, a television adaptation of the classic film.

Sean Patrick Thomas (Ronald Clifford)

Sean Patrick Thomas portrays Ronald Clifford, Cecile's music teacher and lover. After Cruel Intentions, he starred in the hit teen romance film Save The Last Dance. Other films Thomas appeared in include Halloween: Resurrection, the Barbershop franchise, The Fountain, and Till. He starred in several TV series, including The District, Reaper, Ringer (with costar Sarah Michelle Gellar), Vixen, and Reasonable Doubt. Sean Patrick Thomas is returning to Cruel Intentions for the television reboot on Amazon Prime Video.