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Sarah Michelle Gellar Celebrates “Cruel Intentions”' 25th Anniversary: 'Everybody Still Loves You'

The 1999 film - which starred Sarah Michelle Gellar, Ryan Phillippe, Reese Witherspoon and Selma Blair - celebrated its silver anniversary on Tuesday

<p>Columbia Pictures/Courtesy Everett</p> Reese Witherspoon, Ryan Phillippe and Sarah Michelle Gellar in <em>Cruel Intentions</em> (1999)

Columbia Pictures/Courtesy Everett

Reese Witherspoon, Ryan Phillippe and Sarah Michelle Gellar in Cruel Intentions (1999)

Cruel Intentions is 25!

The dark romantic teen drama celebrates its silver anniversary on Tuesday, and one of its stars, Sarah Michelle Gellar, is celebrating the movie's milestone birthday by sharing promotional images from the 1999 movie to Instagram.

"Happy 25th #cruelintentions." Gellar, 46, wrote in a caption to her post "Everybody still loves you, and I intend to keep it that way."

Reese Witherspoon also commemorated the day on Instagram, writing, "Cue Bitter Sweet Symphony 🎶💗🥂 Happy 25th Anniversary to Cruel Intentions!"

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Reese Witherspoon and Ryan Phillippe in <em>Cruel Intentions</em> (1999)
Reese Witherspoon and Ryan Phillippe in Cruel Intentions (1999)

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

Gellar costarred with Ryan Phillippe, Witherspoon and Selma Blair in Cruel Intentions, based on Pierre Choderlos de Laclos' 1782 novel Dangerous Liaisons.

The movie, written and directed by Roger Kumble, follows Annette Hargrove (Witherspoon, now 47), the daughter of the new headmaster at a private high school in New York City.

Wealthy Upper East Sider step-siblings Kathryn Merteuil (Gellar) and Sebastian Valmont (Phillippe, now 49) 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, Sean Patrick Thomas, Swoosie Kurtz, Eric Mabius, Christine Baranski, Joshua Jackson, Tara Reid and more.

Columbia/Kobal/Shutterstock Reese Witherspoon and Sarah Michelle Gellar in <em>Cruel Intentions</em> (1999)
Columbia/Kobal/Shutterstock Reese Witherspoon and Sarah Michelle Gellar in Cruel Intentions (1999)

The cast has remained close over the years since Cruel Intentions hit theaters — and Gellar and Blair have even recreated their steamy smooch!

In February 2023, Gellar recalled what was going on behind the camera when they kissed while filming the teen movie on "the first day in all of New York City of that year that was beautiful and sunny," in a very famous location.

"So, where did everybody go for lunch, to walk and be outside? Central Park," she recounted in a video interview with BuzzFeed UK. "Guess where we were filming that scene? Central Park."

"So, we had about 250 audience members; it was like a live performance. But it was so noisy because there were so many people, we had to re-record the entire scene afterward, every line," Gellar continued.

She also remembered Blair's mother complaining: "Did you have to use so much tongue?"

Sony Selma Blair and Sarah Michelle Gellar in <em>Cruel Intentions</em> (1999)
Sony Selma Blair and Sarah Michelle Gellar in Cruel Intentions (1999)

Related: Sarah Michelle Gellar Says 'Cruel Intentions' Costar Selma Blair Has a 'Very Easy Face to Kiss'

In December 2023, Amazon announced an eight-episode order for a television series of the same name inspired by Cruel Intentions, after seven years in development.

Taking place at an elite college in Washington, D.C., the drama series — from writers and executive producers Sara Goodman and Phoebe Fisher — will chronicle “two ruthless step-siblings" who "will do anything to stay on top of the cutthroat social hierarchy."

"After a brutal hazing incident threatens the entire Panhellenic system at their school, they’ll do whatever is necessary to preserve their power and reputation, even if that means seducing the daughter of the vice president of the United States,” according to the streamer.

Along with Thomas, now 53, Sarah Catherine Hook, Zac Burgess, Savannah Lee Smith, Sara Silva, Khobe Clarke, John Harlan Kim and Brooke Lena Johnson are set to star in the series, with Claire Forlani, Nikki Crawford, Isabella Tagliati, Zeke Goodman and Jon Tenney in recurring roles.

Cruel Intentions is available to stream on Prime Video.

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