Quick, turn off the TV, mom's coming!

If you grew up in the '90s or just grew up loving teen movies, you probably said something similar to that while watching Cruel Intentions, the hit 1999 film that had no interest in earning a PG-13 rating or getting along with its contemporaries, like  She's All That and 10 Things I Hate About You. Can you imagine Lainey or Bianca shouting, "I want to f--k!" to their step-brother a la Kathryn Merteuil (Sarah Michelle Gellar)? They would and could never.

The iconic movie was released on March 5, 1999, and quickly become a commercial and cult favorite, a rare feat for any movie, nevertheless a drama centering on high school students, and it's still just as beloved and quoted 20 years later. 

"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," Sarah Michelle Gellar told Entertainment Tonight ahead of the 20th anniversary. "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."

The first of its kind, a surprise success at the box office and the movie that helped launch the careers of Reese Witherspoon and Ryan Phillippe, who got engaged during production, and a then-unknown Selma Blair, with small appearances from some other familiar famous faces mixed in there, too.

We've compiled a list of secrets and behind-the-scenes tidbits from writer and director Roger Kumble, as well as the main stars, including which A-lister was originally approached to play Annette, which former star of The Bachelor was actually in the movie, the Oscar winner who starred in the direct-to-DVD sequel, and the film's original ending, which managed to be even more depressing.

 And don't worry, we didn't forget about that iconic spit-kiss...happy hunting!

Cruel Intentions

Columbia Pictures

I Know What You Did Last Summer

Columbia Pictures

Cruel Intentions

Columbia Pictures

Jonathan Rhys Meyers

AP Photo/Dan Steinberg

Dawson's Creek

Columbia Tristar Television

Cruel Intentions

Columbia Pictures

Christine Baranski, The Good Fight

CBS

Sarah Michelle Gellar, Selma Blair, Cruel Intentions, Kiss

Columbia Pictures

Cruel Intentions

Columbia Pictures

Joshua Jackson, Cruel Intentions

Getty Images

Charlie O'Connell, Sarah Brice, The Bachelor

Jeff Kravitz/FilmMagic

Reese Witherspoon, Cruel Intentions

Columbia Pictures

Cruel Intentions

Columbia Pictures

Ryan Phillippe, Cruel Intentions, Celeb Crushes

Columbia Pictures

90s Movies Couples, Cruel Intentions

Columbia Pictures

Reese Witherspoon, Cruel Intentions

Columbia Pictures

Amy Adams, Oscars Nominee Luncheon 2019

Matt Baron/REX/Shutterstock

Sarah Michelle Gellar, Selma Blair, Cruel Intentions, Reunion, Pink, Concert

Instagram

Cruel Intentions, Reunion, Sarah Michelle Gellar, Reese Witherspoon, Selma Blair

Instagram

Reese Witherspoon, Ryan Phillippe, 2002 SAG Awards

KMazur/WireImage

In honor of its 20th anniversary, Cruel Intentions is heading back to theaters for one week beginning on March 22. 

Don't miss E! News every Tuesday to Saturday at 6pm.

  • Share
  • Tweet

We and our partners use cookies on this site to improve our service, perform analytics, personalize advertising, measure advertising performance, and remember website preferences. By using the site, you consent to these cookies. For more information on cookies including how to manage your consent visit our Cookie Policy.