Cruel Intentions is one of those iconic '90s films that we'll never forget.

The movie, which followed two step-siblings at an elite Manhattan school with a devious plan, tackled a number of taboo topics, making it the kind of film that millennials were forced to watch in secret. (It was rated MA, remember?)

Released in 1999, the film also boosted the careers of several actors, including Sarah Michelle Gellar, Ryan Phillippe, Reese Witherspoon, and Selma Blair. And it's just had a milestone birthday, turning 25 in 2024.

Gellar shared a post on Instagram to mark the cult movie's anniversary on March 6, giving a nod to one of her character, Kathryn Merteuil's, iconic lines in the caption.

Witherspoon, too, posted a tribute to the movie on social media, shouting out the final track of the movie, 'Bitter Sweet Symphony' by The Verve — which will forever be synonymous with Annette speeding down the freeway (IYKYK).

As we reminisce all thingsCruel Intentionson its 25th anniversary, here are nine things you didn't know about the iconic movie.

Katie Holmes was originally up for the role of Annette.

While searching for the perfect fit for the sweet and innocent Annette, producers were drawn to Katie Holmes, who was appearing as Joey onDawson's Creekat the time.

But while the studio were keen to cast Holmes for the role, director Roger Kumble wantedHocus Pocus' Vinessa Shaw instead.

After both sides came to a stalemate, Kumble was drawn to the idea of using Ryan Phillippe's girlfriend, Reese Witherspoon.

While Witherspoon initially turned down the role, she eventually changed her mind.

Watch the trailer for Cruel Intentions below. Post continues after video.

"So, basically, we took Reese out to dinner to get her drunk, andweended up getting drunk. And I literally got down on my knees and begged her: 'Please, it'll be 15 days, you'll be great,'" Kumble told Cosmopolitan .

"And Reese was like, 'I'll do it. But we need to work on the character.' I'm like, 'Anything, anything, anything.' She wanted to strengthen the character, and she was right. And she and I got together, and we gave Annette more bite so she wasn't a doormat. And I'm very grateful to her for that."

Selma Blair used method acting in her audition.

To land the role of Cecile, Selma Blair used method acting in her audition.

Speaking toCosmopolitan,director Kumble shared that it was the "smartest audition" he had seen in his career.

"I remember Selma came in and I said, 'How old are you?' And she goes [in Cecile's bratty voice] 'How old are you?' And she was so obnoxious and I couldn't get it out of my head," he shared.

While Blair plays one of the youngest characters in the movie, she was actually one of the oldest actors in the main cast. (Blair, who was 27, played the 15-year-old Cecile).

Due to some of the more adult situations that Cecile faced in the film, Kumble wanted to make sure they cast someone who was over 18.

The film was originally titledCruel Inventions.

In an Instagram post in 2016, Sarah Michelle Gellar shared that the film was originally titledCruel Inventions.

"Okay, one last one because I was feeling nostalgic and yes,Cruel Inventionswas the original title. This photo was 1998 at our kick off dinner," she shared.