‘Cruel Intentions’ Cast Then & Now: See Reese Witherspoon, Ryan Phillippe & More After 22 Years

‘Cruel Intentions’ became one of the most iconic teen films when it was released in 1999. Over the last two decades, the film has become a cult classic. Take a look at the cast then and now after 22 years.

Cruel Intentions turned the typical ’90s teen movie on its head — and then some. Unlike most of the squeaky clean teen movies of the era, Cruel Intentions was racy, jaw-dropping, and downright sexy. With a killer cast and their explosive chemistry, Cruel Intentions became a film in a league all its own.

The movie starred the hottest young stars of that time, including Reese Witherspoon, Sarah Michelle Gellar, and Ryan Phillippe. Cruel Intentions was released on March 5, 1999, and we’ve all never been able to listen to “Colorblind” by Counting Crows without thinking of this movie since. Find out what the cast is up to after all these years below.

Reese Witherspoon

Reese Witherspoon then and now. (Everett Collection/MEGA)

Cruel Intentions was one of Reese Witherspoon’s breakthrough roles. She starred as the innocent Annette Hargrove in the 1999 teen flick. That same year, she notably played Tracy Flick in Election. Just a few years later, Reese played Elle Woods in Legally Blonde and became a worldwide star. She returned for the 2003 sequel.

Reese, 44, won the Academy Award in 2006 for her performance as June Carter Cash in Walk the Line. She earned her second Oscar nomination for the 2014 drama Wild. She has since transitioned into mostly TV work. She’s produced and starred in a number of series, including Big Little Lies, Little Fires Everywhere, and The Morning Show. Reese is currently filming the second season of The Morning Show.

Reese and Ryan Phillippe met in 1997. They became co-stars in Cruel Intentions in 1998. Reese and Ryan married in June 1999, and their daughter, Ava, was born in September 1999. Their son, Deacon, was born in Oct. 2003. The couple separated in 2006. Reese married Jim Toth in 2011. Their son, Tennessee, was born in Sept. 2012.

Ryan Phillippe 

Ryan Phillippe
Ryan Phillippe then and now. (Everett Collection/Shutterstock)

Ryan Phillippe, 46, starred as the very charming bad boy Sebastian Valmont in Cruel Intentions. This was his second film with SMG after I Know What You Did Last Summer. Ryan went on to star in films like Gosford Park, Igby Goes Down, Crash, Flags of Our Fathers, The Lincoln Lawyer, and more. He produced and starred in the USA Network series Shooter, which ran from 2016 to 2018. He recently appeared in the ABC series Big Sky.

Ryan and Reese married in 1999 and had two children together. He started dating Abbie Cornish in 2007, but they split in 2010. He began dating Alexis Knapp in 2010, but they split the same year. Alexis gave birth to their daughter in 2011. Elsie Hewitt, an ex-girlfriend, accused of allegedly kicking her, punching her, and throwing her down a flight of stairs, according to PEOPLE. She was granted a restraining order in 2019. The case was settled that same year.

Sarah Michelle Gellar

Sarah Michelle Gellar
Sarah Michelle Gellar then and now. (Everett Collection/MEGA)

In one of her most iconic roles, Sarah Michelle Gellar, 43, starred as the manipulative and chaotic Kathryn Merteuil in Cruel Intentions. At the time, she was starring as Buffy Summers in Buffy the Vampire Slayer. The series ran from 1997 to 2003. After Cruel Intentions, Sarah played the live-action version of Daphne in the Scooby Doo movies. Another one of her major roles was in the horror film The Grudge. SMG returned to TV in The CW drama Ringer and The Crazy Ones. She co-founded Foodstirs in 2015, a startup selling baking kits.

Sarah and Freddie Prinze Jr. started dating in 2000 after meeting on the set of I Know What You Did Last Summer. They married in 2002 and have two kids together.

Selma Blair 

Selma Blair
Selma Blair then & now. (Everett Collection/MEGA)

Selma Blair, 48, played the gullible Cecile Caldwell in Cruel Intentions. She reunited with Reese in the 2001 comedy Legally Blonde. She went on to star as Liz Sherman in Hellboy and Hellboy II: The Golden Army. She’s also starred in The Sweetest Thing, A Guy Thing, Mothers and Daughters, and After. Selma had TV roles in Kath & Kim, Anger Management, and notably played Kris Jenner in the first season of American Crime Story.

She married Ahmet Zappa in 2004. They divorced in 2006. She dated Mikey Day from 2008 to 2010. She began dating Jason Bleick in 2010. Their son, Arthur, was born in 2011. They broke up in 2012. Selma revealed in Oct. 2018 that she had been diagnosed with multiple sclerosis.

Sean Patrick Thomas

Sean Patrick Thomas
Sean Patrick Thomas then and now. (Everett Collection/Shutterstock)

Sean Patrick Thomas, 50, starred as Ronald Clifford. His breakthrough role came a few years later in the 2001 movie Save the Last Dance. He went on to star in Barbershop and Halloween: Resurrection in 2002. He reprised the role of Jimmy James in later Barbershop films. He’s also appeared in TV shows like RingerAmerican Horror Story: AsylumMadam Secretary, and The Good Fight. He is set to play Monteith in the upcoming Joel Coen film, Macbeth, with Denzel Washington.

Joshua Jackson

Joshua Jackson
Joshua Jackson then and now. (Everett Collection/MEGA)

Joshua Jackson, 42, played Blaine Tuttle in Cruel Intentions. At the time of the movie’s release, Joshua was starring as Pacey Witter in the hit teen series Dawson’s Creek, which ran from 2008 to 2003. He later starred as Peter Bishop in Fringe from 2008 to 2018. Joshua also starred in TV series like The Affair, When They See Us, and Little Fires Everywhere. He is currently filming the upcoming limited series Dr. Death.

Joshua dated actress Diane Kruger from 2006 to 2016. He began dating actress Jodie Turner-Smith in 2018. They married in 2019 and welcomed their first child in 2020.

Christine Baranski 

Christine Baranski
Christine Baranski then and now. (Everett Collection/MEGA)

Christine Baranski, 68, played Bunny Caldwell, Cecile’s mother, in Cruel Intentions. Following the teen flick, Christine starred in movies like How the Grinch Stole Christmas, Chicago, A Bad Moms Christmas, as well as Mamma Mia! and its sequel. She notably played Diane Lockhart in the CBS series The Good Wife from 2009 to 2016. She earned 6 Emmy nominations during the show’s run. She reprised the role of Diane in The Good Wife spinoff, The Good Fight, which has been renewed for a fifth season. Christine recently starred in the Netflix holiday film Dolly Parton’s Christmas on the Square and will star in the upcoming HBO series The Gilded Age.

Christine’s husband, Matthew Cowles, died in 2014. They have two daughters together.

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