The drama, which starred Sarah Michelle Gellar, Ryan Phillippe and Reese Witherspoon, hit theaters March 5, 1999.
It's been 20 years since Cruel Intentions premiered in theaters on March 5, 1999.
The film follows two vicious step-siblings, Kathryn (Sarah Michelle Gellar) and Sebastian (Ryan Phillippe), who attend an elite private school in Manhattan. Drama ensues when Kathryn bets Sebastian that he can't deflower the new headmaster's daughter (Reese Witherspoon) before the start of the term. If Kathryn wins, she gets his vintage Jaguar XK140. If Sebastian wins, Kathryn says she'll sleep with him.
Cruel Intentions is a modern-day adaptation of Pierre Choderlos de Laclos' 1782 novel Les Liaisons dangereuses.
Despite receiving mixed reviews, the film earned $75 million worldwide and became a fan favorite, spawning two sequels, neither of which starred the original cast, and an off-Broadway musical. Gellar, Witherspoon and co-star Selma Blair even took in a 2015 performance of the Cruel Intentions musical in Los Angeles.
To celebrate the film's 20th anniversary, Cruel Intentions will return to theaters for a one-week engagement on March 22.
Read on to see what the cast has been up to since their days of high-school scheming.
Gellar starred as Kathryn, a wealthy, popular and manipulative member of the Upper East Side's social elite. While Kathryn portrayed herself as a deeply religious high school student, she often schemed to destroy other people for her own amusement. Since filming Cruel Intentions, Gellar has gone on to star in films including Harvard Man, Scooby-Doo, Scooby-Doo 2: Monsters Unleashed, Southland Tales, The Return, Happily N'Ever After, Suburban Girl, The Air I Breathe, Possession and Veronika Decides to Die. She also starred as the titular character on TV's Buffy the Vampire Slayer from 1997 to 2003. Her other TV credits include guest spots on Sex and the City, The Simpsons and American Dad! Gellar also starred on the CW thriller Ringer from 2011 to 2012 and alongside Robin Williams on the CBS sitcom The Crazy Ones from 2013 to 2014.
Phillippe played Sebastian, a sexually promiscuous teenager who is obsessed with his step-sister. Sebastian often documents his sexual conquests in a journal that he regularly writes in throughout the film. After starring in Cruel Intentions, Phillippe went on to appear in films including The Way of the Gun, Antitrust, Gosford Park, Crash, Flags of Our Fathers and The Lincoln Lawyer. He also directed, wrote, produced and starred in the 2014 thriller Catch Hell. His television credits include a starring role on the final season on Damages, as well as guest starring roles on Men at Work, Drunk History and Robot Chicken. Phillippe starred on the first season of ABC's anthology police detective series Secret and Lies in 2015, which was followed by his starring role on USA Network's Shooter from 2016 to 2018. Phillippe married his Cruel Intentions co-star Witherspoon in 1999, though they announced their separation in 2006 and subsequently divorced. They share two children.
Witherspoon portrayed Annette, the new headmaster's daughter who wrote an essay that declared she would not have sex until she was in love. The actress has kept busy since Cruel Intentions. She starred as Elle Woods in the 2001 film Legally Blonde and its 2003 sequel Legally Blonde: Red, White & Blonde. Witherspoon also starred in American Psycho, Sweet Home Alabama, Vanity Fair, Just Like Heaven, Penelope, Four Christmases, How Do You Know, Water For Elephants, Mud, Wild, Hot Pursuit, Home Again and A Wrinkle In Time. She won an Academy Award, BAFTA Award and Golden Globe for her performance as June Carter in 2005's Walk the Line. Witherspoon has also produced a number of films, including Penelope, Gone Girl, Wild, Hot Pursuit and the upcoming drama Pale Blue Dot. On the TV side, she has had guest starring roles on King of the Hill, Friends, The Simpsons and The Mindy Project. Witherspoon currently serves as an executive producer and star on the HBO series Big Little Lies, which has earned her Emmy and Golden Globe awards. In addition to the highly anticipated second season of the drama, Witherspoon will next be seen alongside Jennifer Aniston and Steve Carell in Apple's upcoming TV series about broadcast morning shows and in the third Legally Blonde film.
Kathryn was recruited to take sheltered and naive Cecile (Blair) under her wing and turn her into a model student, though Kathryn used the opportunity to seek revenge against an ex-boyfriend who was dating Cecile. Following Cruel Intentions, Blair went on to appear in films including Down to You, Legally Blonde, The Sweetest Thing, A Guy Thing, Hellboy and Mom and Dad. She will next appear in the movie After, which is set to hit theaters in April. Blair's television credits include the starring role of Kim in NBC's Kath & Kim from 2008 to 2009, and she played Dr. Kate Wales in FX's sitcom Anger Management, which ran from 2012 to 2014. The actress also recently played Kris Jenner in The People v. O.J. Simpson: American Crime Story. In October of last year, Blair revealed that she had been diagnosed with multiple sclerosis.
Blaine Tuttle was a high school student and friend of Sebastian's. After Sebastian persuaded Blaine to seduce Annette's closeted ex-boyfriend Greg, the main character used photos from the affair to blackmail Greg. Jackson was starring as Pacey Witter on The WB's Dawson's Creek when Cruel Intentions debuted. Following the end of that series in 2003, Jackson went on to star on the Fox supernatural drama Fringe for five seasons. He recently starred on the Showtime series The Affair, though left the drama at the end of the fourth season. The former child star will next appear in the upcoming Netflix series When They See Us, which was created by Ava DuVernay.
Ronald is Cecile's music teacher. After he confesses to Kathryn that he loves Cecile, Kathryn tells Cecile's mother, who forces them to end the romance. Since his role as Ronald, Thomas went on to star in the 2001 teen dance drama Save the Last Dance opposite Julia Stiles. His other film credits include Barbershop, Halloween: Resurrection, Barbershop 2: Back in Business, Barbershop: The Next Cut and The Sterling Case. He will next appear in the supernatural horror The Curse of La Llorona. On the TV side, Thomas starred as Detective Temple Page on the CBS police procedural drama The District from 2000 to 2004. He also has made guest appearances on Lie to Me, Ringer, American Horror Story: Asylum, NCIS: New Orleans, Criminal Minds, Kevin (Probably) Saves the World and Madam Secretary.