Cruel Intentions Turns 25: The Actors You Forgot Starred in the Cult Classic, from Joshua Jackson to Tara Reid

The cast Cruel intentions was complex — and that’s not even considering the four cores.

The dark 1999 teen drama-romance turns 25 on Tuesday, and many of its stars have since gone on to have successful careers, including leads Sarah Michelle Gellar, Ryan Phillippe, Reese Witherspoon and Selma Blair.

But several other notable actors appeared in the film in minor roles, such as Joshua Jackson, Christina Baranski, Tara Reid and Sean Patrick Thomas.

Jackson, now 45, played Blaine Tuttle, a flamboyant character with cool hair who gets caught up in one of Sebastian’s (Phillippe, now 49) schemes — a far cry from his small-town character on the then-hit series Dawson’s CreekPacey Witter.

Baranski, now 71, played Bunny Caldwell, the overbearing mother of Blair’s naïve Cecile, while Reid, now 48, had a small role as Marcia Greenbaum, the daughter of Sebastian’s therapist. She would continue to appear as Vicky American Pie a few months later, it effectively catapulted her to stardom.

Thomas, 53, made a special appearance as Blair’s character’s music teacher, Ronald Clifford, in the 2001 teen romance. Save the last dance after Cruel intentionsand continued to appear in Barber shop franchise as well as movies including Halloween: Resurrection (2002), Deep in the dark (2014) and To (2022).

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Reese Witherspoon, Ryan Phillippe and Sarah Michelle Gellar Cruel intentions (1999).

Columbia Pictures/Courtesy of Everett

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The cast Cruel intentions: Where are they now?

Cruel intentions based on the 1782 novel by Pierre Choderlos de Laclos Dangerous Liaisons, and was written and directed by Roger Kumble.

It tells the story of Annette Hargrove (Witherspoon, now 47), the daughter of the new principal of a private high school in New York. Wealthy Upper East Sider half-siblings Kathryn Merteuil (Gellar, now 46) and Sebastian Valmont (Phillippe) are among Annette’s classmates, and the two make a bet that Sebastian can’t seduce the virginal new student.

Known for its sexy, subversive storylines and dialogue (including an unforgettable kiss between Gellar and Blair, now 51), the film stood out among mid-to-late ’90s teen comedies and dramas that were often based on literary works, many William Shakespeare.

Cruel intentions also included a supporting cast of Louise Fletcher (Oscar winner for one flight over the cuckoo’s nest), Swoosie Kurtz, Eric Mabius and others.

Ryan Phillippe as Sebastian Valmont and Selma Blair as Cecile Caldwell 'Cruel Intentions' movie - 1999 Two vicious half-siblings from an elite prep school in Manhattan make a bet: devirginize the new principal's daughter before the start of the semester.

Enter Ryan Phillippe and Selma Blair Cruel intentions (1999). Columbia/Sony/Kobal/Shutterstock Amazon finally caught on Cruel intentions The series that was first shown in 2016

Gellar, who plays a wicked queen bee caught up with karma, admitted earlier in 2019 that she didn’t realize it was the 20th anniversary Cruel intentions.

“Wait… 20 years today?!? I literally just realized today is the actual anniversary,” she captioned the post, which included a poster from the movie featuring her with Phillippe, Witherspoon and Blair. “Well, 20 years from now I might be even more proud of this movie.”

Gellar continued, “It’s rare that you get to be part of a piece of cinema that stands the test of time. @rogerkumbleti you are the most wonderfully deranged person I know and I love you. @reesewitherspoon @selmablair @ryanphillippe (and not pictured @seanpthomas @vancityjax) you are even better actors and better people than you were then.”

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“Forget me – everyone loves this movie and I intend to keep it that way. #cruelintentions #cruelinventions,” she concluded.

Cruel intentions is available to stream on Prime Video.

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Source: HIS Education

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