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‘Cruel Intentions’ Turns 20! To Celebrate, See the Movie’s Star-Studded Cast Then and Now

News

Mar 5, 2019 7:37 pm·

By Julia Birkinbine

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Can you believe Cruel Intentions first hit movie screens 20 years ago today?! We certainly can’t! Back in 1999, the cult-classic flick helped propel the acting careers of young stars including Reese Witherspoon, Sarah Michelle Gellar, Ryan Phillippe, Selma Blair and more — and the movie is still beloved today, two decades later!

To celebrate Cruel Intentions turning 20, scroll down to see the film’s cast then and now!

1 of 16

Then: Sarah Michelle Gellar

Back in 1999, Sarah Michelle — who played Kathryn Merteuil in Cruel Intentions — was one year into portraying Buffy on Buffy the Vampire Slayer and still a few years away from marrying her I Know What You Did Last Summer costar Freddie Prinze Jr.

2 of 16

Now: Sarah Michelle Gellar

Today, Sarah Michelle is 41 years old and a mom-of-two! She recently starred on the TV show The Crazy Ones and even reprised her role as Kathryn in the Cruel Intentions television reboot, which has yet to be picked up.

3 of 16

Then: Reese Witherspoon

Twenty years ago, Reese was known for starring in the movies Pleasantville and Overnight Delivery before landing the role of Annette Hargrove in Cruel Intentions. The same year Cruel Intentions hit theaters, the young actress married her costar Ryan Phillippe in June 1999.

4 of 16

Now: Reese Witherspoon

Today, Reese, 42, is a mom-of-three and, after divorcing Ryan in 2007, she tied the knot with current husband Jim Toth in 2011. In addition to starring in hit movies including Election, American Psycho, Legally Blonde, Sweet Home Alabama, Walk the Line, Wild and A Wrinkle in Time, the Oscar winner now has her own successful clothing line, Draper James, and runs a production company called Hello Sunshine.

5 of 16

Then: Ryan Phillippe

When he portrayed Sebastian Valmont in Cruel Intentions, Ryan was engaged to his costar Reese — whom he later married in June 1999 — and had already starred in the popular movie I Know What You Did Last Summer.

6 of 16

Now: Ryan Phillippe

Since Cruel Intentions, father-of-three Ryan, now 44, has appeared in movies Flags of Our Fathers and The Lincoln Lawyer and had a lead role on the TV show Shooter.

7 of 16

Then: Selma Blair

In the late 1990s, Selma played Cecille Caldwell in Cruel Intentions before moving onto other movie roles in Legally Blonde, The Sweetest Thing, and Hellboy.

8 of 16

Now: Selma Blair

Today, the mom-of-one, 46, has taken a slight step away from acting after being diagnosed with Multiple Sclerosis. “I am disabled. I fall sometimes. I drop things. My memory is foggy. And my left side is asking for directions from a broken GPS. But we are doing it. And I laugh and I don’t know exactly what I will do precisely but I will do my best,” Selma wrote via Instagram when she revealed her diagnosis.

9 of 16

Then: Joshua Jackson

Joshua portrayed Blaine Tuttle in Cruel Intentions back in 1999 during his run as Pacey Witter on the hit TV show Dawson’s Creek.

10 of 16

Now: Joshua Jackson

Since then, Joshua, 40, is known for starring on TV shows Fringe and The Affair.

11 of 16

Then: Sean Patrick Thomas

In Cruel Intentions, Sean Patrick played Ronald Clifford. Two years later, he starred in the hit 2001 film Save the Last Dance.

12 of 16

Now: Sean Patrick Thomas

Today, Sean Patrick is 48 years old and a father-of-two. From 2000 until 2004, the actor portrayed Detective Temple Page in The District and also recently appeared in five episodes of Ringer.

13 of 16

Then: Christine Baranski

Before portraying Bunny Caldwell in Cruel Intentions back in 1999, Christine starred on TV shows Cybill and Another World in appeared in movies The Birdcage, Addams Family Values and The Ref.

14 of 16

Now: Christine Baranski

Since Cruel Intentions, Christine, 66, has starred in popular films including How the Grinch Stole Christmas, Mamma Mia!, Into the Woods, Trolls, and Chicago. She’s also appeared in TV shows The Good Wife, The Good Fight and The Big Bang Theory.