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

The 1999 drama, led by Sarah Michelle Gellar, Ryan Phillippe, Reese Witherspoon and Selma Blair, turns 25 on Tuesday

The cast of Cruel Intentions was stacked — and that's not even considering the core four.

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

But several other notable actors appeared in the film in smaller roles, like Joshua Jackson, Christine Baranski, Tara Reid and Sean Patrick Thomas.

Jackson, now 45, played Blaine Tuttle, a flamboyant character with frosted 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 show Dawson's Creek, Pacey Witter.

Baranski, now 71, played Bunny Caldwell, the overbearing mother of Blair's naïve Cecile, while Reid, now 48, had a small role as Marci Greenbaum, the daughter of Sebastian's therapist. She would go on to appear as Vicky in American Pie a few months later, effectively catapulting her to stardom.

Thomas, 53, as Blair's character's music teacher Ronald Clifford, notably starred in the 2001 teen romance film Save the Last Dance after Cruel Intentions, and went on to appear in the Barbershop franchise, as well as movies including Halloween: Resurrection (2002), Deep in the Darkness (2014) and Till (2022).

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Related: The Cast of Cruel Intentions: Where Are They Now?

Cruel Intentions is based on Pierre Choderlos de Laclos' 1782 novel 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 headmaster at a private high school in New York City. Wealthy Upper East Sider stepsiblings 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 a memorable kiss between Gellar and Blair, now 51), the movie was a standout among the teen comedies and dramas of the mid to late '90s that were often based on literary works, many by William Shakespeare.

Cruel Intentions also featured a supporting cast of Louise Fletcher (an Oscar winner for One Flew Over the Cuckoo's Nest), Swoosie Kurtz, Eric Mabius and more.

Related: Amazon Finally Picks Up Cruel Intentions Series That Was First Floated in 2016

Gellar, playing a vicious Queen Bee whose karma catches up with her, previously admitted back in 2019 that she didn't realize it was the 20th anniversary of Cruel Intentions.

“Wait … today 20 years?!? I literally just realized today is the actual anniversary,” she wrote in the caption of a post, which included a poster from the film that featured herself with Phillippe, Witherspoon and Blair. "Well 20 years later I may be even more proud of this film.”

Gellar continued, “Not very often do you get to be a part of cinema, that holds the test of time. @rogerkumbleyou are the most wonderfully disturbed person I know and I love you. @reesewitherspoon @selmablair @ryanphillippe (and not pictured @seanpthomas @vancityjax) you are even better actors and better people then you were then."

"Forget me - everybody loves this film 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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