In 1999 a little film by the name of Cruel Intentions arrived in theaters and surprised everyone by unexpectedly becoming an enduring cult favorite. Starring Sarah Michelle Gellar, Reese Witherspoon, and Ryan Phillippe, this teen drama adapted from the French novel Les Liaisons dangereuses is a cinematic classic about a provocative bet between two affluent step-siblings. Need a refresher? Take a look at the trailer in all of its quintessential ’90s glory below.
So what have the stars of Cruel Intentions been up to for the past 16 years? Let’s find out!
1. Sarah Michelle Gellar
Business: After her role scene-stealing role in Cruel Intentions, Gellar went on to star in a slew of films, including Scooby-Doo and The Grudge. While she’ll always be remembered by fans for her portrayal of Buffy Summers, Gellar returned to television in 2011 starring in the short-lived CW series Ringer. In 2013, she starred opposite the late Robin Williams on CBS’ The Crazy Ones, and last year the actress lent her voice to the animated series Star Wars Rebels. Next up, Gellar is returning to the character that started it all. She just announced that she’ll be reprising her role as Kathryn in the upcoming NBC reboot of Cruel Intentions.
Personal: SMG married her frequent co-star FPJ (Freddie Prinze, Jr.) back in 2002. The couple have two children together.
2. Reese Witherspoon
Business: Witherspoon has had the most commercial success out of her Cruel Intention cohorts. She’s appeared in countless romantic comedies, but is perhaps best known for her mainstream films Legally Blonde and Sweet Home Alabama, as well as her late ’90s hits Election and Pleasantville. Most recently, Witherspoon earned an Academy Award nomination for her role in the critically acclaimed 2014 film Wild, and appeared opposite Sofía Vergara in the 2015 comedy Hot Pursuit.
Personal:After her divorce from Phillippe, Witherspoon dated Jake Gyllenhaal before the couple split in 2009. She is now married to talent agent Jim Toth. The couple have one son together.
3. Ryan Phillippe
Business: Phillippe continues to enjoy an eclectic acting career. In 2010 he co-starred in the comedy MacGruber and in 2012 he had a recurring role on the television series Damages. Most recently, Phillippe appeared on an episode of Comedy Central’s Drunk History and starred in the first season of the ABC anthology series Secrets and Lies.
Personal: Phillippe married his Cruel Intentions co-star Reese Witherspoon in 1999, but the couple divorced in 2006. He shares two children with Witherspoon and also has a child with model/actress Alexis Knapp.
4. Selma Blair
Business: Blair has maintained quite the prolific Hollywood career. After reuniting with her Cruel Intentions co-star Reese Witherspoon in the 2001 hit Legally Blond, Blair has appeared in an impressive mix of mainstream and indie movies. After co-starring on the Charlie Sheen series Anger Management, Blair nabbed the high-profile role of Kris Jenner in FX’s The People v. O.J. Simpson.
Personal: Blair has a four-year-old son with fashion designer Jason Bleick.
5. Joshua Jackson
Business: J-Squared, as he’s referred to in the unofficial fan club we created back in 1998, was king of the late ’90s to early 2000s teen movie genre. After appearing in Scream 2, Apt Pupil, Urban Legend, The Skulls, Gossip and the aforementioned Cruel Intentions, the former Mr. Witter of Dawson’s Creek took a mini sabbatical before returning to television as Peter Bishop in the sci-fi drama Fringe. Jackson currently stars on Showtime’s The Affair, which won the 2015 Golden Globe for Best Dramatic Television Series.
Personal: Jackson has been dating actress Diane Kruger since 2006.
Who was your favorite character from Cruel Intentions?
(The headline and content of this post was updated on Feb. 24, 2016 to reflect the most recent information about each of the stars featured.)