It was a teen movie that broke boundaries and launched the acting careers of Reese Witherspoon, Selma Blair, Ryan Phillippe and Sarah-Michelle Gellar.
But one of Cruel Intentions' most memorable scenes would probably have ended up on the cutting room floor if it was made today.
Reflecting on the movie's legacy 20 years after its release in Entertainment Weekly, Philippe said he had mixed feelings about the sex scene between his character Sebastian and Cecile, played by Blair.
In Cruel Intentions, womanising teen Sebastian sleeps with the younger, inexperienced Cecile after blackmailing her — something that wouldn't sit right with a post #MeToo audience.
"At that age, it didn't feel as lascivious," Philippe told EW. "I'm not sure I saw it the same way you would see it in retrospect."