Entertainment Movies 'Cruel Intentions' Turns 23! See the Cast from the Hit Teen Movie Then and Now Twenty-three years later, see what the all-star cast members — including Sarah Michelle Gellar and Reese Witherspoon — are up to today By Eric Todisco Updated on March 5, 2022 11:42 AM Share Tweet Pin Email Trending Videos 01 of 08 Sarah Michelle Gellar Melissa Moseley/Columbia/Kobal/REX/Shutterstock; Paul Archuleta/Getty Since her role as the wealthy and popular teen Kathryn, Gellar had her most famous role on the CW series Buffy the Vampire Slayer. Additionally, she appeared in the Scooby-Doo films and short-lived shows Ringer and The Crazy Ones. She is married to fellow actor Freddie Prinze Jr. and has two children. 02 of 08 Reese Witherspoon Melissa Moseley/Columbia/Kobal/REX/Shutterstock; Jon Kopaloff/FilmMagic Witherspoon has had a booming career since playing virgin daughter Annette Hargrove. Her roles in films like Election, Legally Blonde and Walk the Line garnered her praise and various award nominations and victories. Most recently, she both produced and starred in HBO's hit show Big Little Lies and scored awards nominations for The Morning Show. She was married to Cruel Intentions costar Ryan Phillippe for seven years, and has two children with him. She remarried in 2011 to talent agent Jim Toth, with whom she has one son. 03 of 08 Ryan Phillippe Melissa Moseley/Columbia/Kobal/REX/Shutterstock; Taylor Hill/FilmMagic Phillippe was the lead role and producer for USA Network's Shooter from 2016 to 2018. He has appeared in several films such as Oscar winner Crash. He has three children: two with Witherspoon and one with model Alexis Knapp. 04 of 08 Selma Blair Melissa Moseley/Columbia/Kobal/REX/Shutterstock; JEAN-BAPTISTE LACROIX/AFP/Getty Alongside Witherspoon, Blair starred in the 2001 comedy Legally Blonde, followed by her role in Hellboy in 2004. She also appeared in television shows Anger Management and as Kris Jenner in the inaugural season of American Crime Story. In 2018, the mom of one revealed she had been diagnosed with multiple sclerosis. 05 of 08 Joshua Jackson Melissa Moseley/Columbia/Kobal/REX/Shutterstock; Slaven Vlasic/Getty Following Cruel Intentions, Jackson rose to further fame from lead roles in popular teen drama Dawson's Creek and sci-fi series Fringe. Other roles include horror film Shutter and Showtime drama series The Affair. He recently married actress Jodie Turner-Smith; the two welcomed their first child in April of 2020. 06 of 08 Sean Patrick Thomas Melissa Moseley/Columbia/Kobal/REX/Shutterstock; Steve Granitz/WireImage After playing Ronald Clifford, Thomas kept a low profile, most notably appearing in teen romance film Save the Last Dance. He starred in CBS crime drama The District from 2000 to 2004, and most recently made an appearance in Madam Secretary, also on CBS. 07 of 08 Eric Mabius Columbia Pictures/courtesy Everett; AFF-USA/REX/Shutterstock Mabius is best known for being a part of the main cast of ABC comedy Ugly Betty. He also appeared on the Showtime series The L Word and has more recently taken the lead of the Hallmark Channel's TV movies Signed, Sealed and Delivered. 08 of 08 Christine Baranski Melissa Moseley/Columbia/Kobal/REX/Shutterstock; Andrew H. Walker/Variety/REX/Shutterstock The screen and stage veteran came to Cruel Intentions having recently appeared in The Birdcage (1996) and Bulworth (1998). Her performance as Blair's overbearing mother led to more comedic performances in Bowfinger (1999) and the Mamma Mia films. On TV, she's best known for her role as Diane Lockhart in The Good Wife (2009 to 2016) and its spinoff The Good Fight.