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."
Gellar also agreed, adding: "What they're doing to her is horrible. We could never make that scene today, let's put it that way."
Speaking to EW, Witherspoon also revealed she had to be convinced to take on the role of Annette, the virgin love interest of Sebastian, despite Phillippe being her boyfriend (and later husband) at the time.
Witherspoon only agreed to join the cast after fleshing out the character alongside the movie's director and writer, Roger Kumble.
"I remember finding Annette too demure and too much of a woman influenced by a guy's manipulations," Witherspoon said.
"I was starting what I guess became my bigger mission in life — of questioning why women were written certain ways on film."
Kumble credits Witherspoon's rewrite as the reason why Cruel Intentions still resonates with audiences two decades later.
"It's true, she came and sat with me for a week, and we worked on the dialogue together," he said.
"Annette was the character most removed from me. There's no way the movie would have its success if it weren't for (Witherspoon's) talent as a writer."