While Sarah Michelle Gellar and Reese Witherspoon celebrated the milestone, Ryan Phillippe had a hilariously different reaction.
The Cruel Intentions cast is celebrating their latest milestone anniversary -- though it's making some feel their age!
The risqué teen drama -- a modern retelling of Pierre Choderlos de Laclos' 1782 novel Les Liaisons dangereuses -- was a major hit upon its release in 1999, and remains popular to this day.
The film starred Sarah Michelle Gellar and Ryan Phillippe as scandalous step-siblings and NYC socialites, who scheme to rope an innocent new classmate -- played by Reese Witherspoon -- into their world of drugs and debauchery.
Even more iconic '90s teen stars appeared in supporting roles, like Selma Blair, Joshua Jackson, Sean Patrick Thomas and Tara Reid.
Gellar and Witherspoon both took to Instagram on Tuesday to mark the film's 25th anniversary, with Gellar quoting one of her character's iconic lines.
"Happy 25th #cruelintentions Everybody still loves you, and I intend to keep it that way," she wrote.
"Cue Bitter Sweet Symphony 🎶💗🥂 Happy 25th Anniversary to Cruel Intentions!" Witherspoon added in her post, referencing the film's equally. memorable soundtrack.
However, the celebration had Phillippe feeling his age, as he shared an anniversary post on X, captioning it simply "damn," with a dinosaur emoji.
Cruel Intentions notably also marked the beginning of Witherspoon and Phillippe's real-life romance. The pair tied the knot just a few months after the film's release, but divorced in 2008. They share two children, daughter Ava, 24, and son Deacon, 20.
Gellar opened up to ET about signing on for the sexy film -- a precursor to the mature teen dramas to come like Gossip Girl and The O.C. -- around the time of the film's 20th anniversary back in 2019.
"I mean, Cruel was exciting because, for me, I look for things that'll make an impact and something that's different. And teen movies at that point were teen movies," she explained. "We were coming out of a John Hughes era and moving into these sort of frothy, romantic comedies, and to take material like Les Liaisons Dangereuses, and give it to teens and that material, it was sort of the first of its kind."
"It was daring and edgy, and some people were against the movie and didn't think it was a good idea," Gellar recalled. "[But] I think we always knew that we were doing something really cool."
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