Christine Baranski, Joshua Jackson and Tara Reid inCruel Intentions(1999).Photo:Melissa Moseley/Columbia/Kobal/Shutterstock; Columbia Pictures/courtesy Everett Collection; Columbia Pictures

Melissa Moseley/Columbia/Kobal/Shutterstock; Columbia Pictures/courtesy Everett Collection; Columbia Pictures
The cast ofCruel Intentionswas 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 leadsSarah Michelle Gellar,Ryan Phillippe,Reese WitherspoonandSelma Blair.
But several other notable actors appeared in the film in smaller roles, likeJoshua Jackson,Christine Baranski,Tara ReidandSean 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 showDawson’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 inAmerican Piea 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 filmSave the Last DanceafterCruel Intentions, and went on to appear in theBarbershopfranchise, as well as movies includingHalloween: Resurrection(2002),Deep in the Darkness(2014) andTill(2022).
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Reese Witherspoon, Ryan Phillippe and Sarah Michelle Gellar inCruel Intentions(1999).Columbia Pictures/Courtesy Everett

Columbia Pictures/Courtesy Everett
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.
Cruel Intentionsalso featured a supporting cast ofLouise Fletcher(an Oscar winner forOne Flew Over the Cuckoo’s Nest),Swoosie Kurtz,Eric Mabiusand more.
Ryan Phillippe and Selma Blair inCruel Intentions(1999).Columbia/Sony/Kobal/Shutterstock

Gellar, playing a vicious Queen Bee whose karma catches up with her, previously admitted back in 2019 that she didn’t realize it was the20th anniversary ofCruel 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 Intentionsis available to stream on Prime Video.
source: people.com