Breaking down the success of Cruel Intentions 20 years later

After 20 years, Cruel Intentions remains one of the most unique cutthroat cult classics about devious youth with an unforgettable cast.

Cruel Intentions debuted 20 years ago this week, initially marketed as a teen-drama that was unlike any film that came prior to its release. The 1999 film starred Sarah Michelle Gellar, Reese Witherspoon, Ryan Phillippe, and Selma Blair as several New York socialites in training from a prep school where Gellar’s character Kathryn reigns supreme.

When Witherspoon’s character Annette relocates to the school, where her father is the new headmaster, a series of twisted games commence. Annette, who is also known for a published essay about maintaining her virginity, becomes a hot topic and leads to a bet between Kathryn and her womanizing stepbrother, Sebastian. Kathryn tells Sebastian that if he can sleep with her and tarnish her virtuous reputation, he can obtain his prize, which is a physical relationship with Kathryn. And so begins a twisted tale of sexuality, love, code-switching and youthful recklessness that is easily superior to other films of the same nature.

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Gellar provided countless iconic moments in Cruel Intentions, with her various personas ranging from kind prep-school queen to sharp-tongued rebel with an addiction to cocaine. Gellar (while still filming Buffy the Vampire Slayer) proved the mean-streak she could portray in such a memorable way, you could almost find yourself rooting for the deeply troubled socialite. During Gellar’s last scene, where the truth is unraveled, she sheds the remarkable single tear and it cements her reputation as a dynamic actress that continues to prove herself due to her massive range.

As for the character Kathryn, well, let’s just say that she would have absolutely dominated on Real Housewives of New York City or any endeavor in her sights. The film also included an on-screen kiss between Gellar and Blair that went on to win an MTV Movie Award and is still regarded as one of the steamiest scenes from dialogue to the sexuality in something as simple as a kiss. If all of that isn’t enough to convince you, her role essentially gave opportunities to series like Gossip Girl or Pretty Little Liars that ended up trying to (unsuccessfully) recreate the twists and turns of that niche group of wicked youth.

Cruel Intentions didn’t just provide us with the unforgettable character Kathryn (Gellar) but is a prime example of the solid creativity that came from 90s cinema. It felt entirely original, was devilishly thrilling, and is a rare film that is able to conjure up a desire of repeat viewings. Even the fashion of Cruel Intentions stood out as some of the best mid to late 90’s trends, providing an aesthetic appeal that has lasted two decades and counting.

Another crucial piece of Cruel Intentions success comes from Phillippe’s charm as Sebastian that drew in viewers. His role helped him become a 90s and 00s heartthrob that, to this day, is a talked about pop-culture contribution. The film showcased major real-life chemistry between his character and Annette (Witherspoon) as a perfect example of opposites attract, a timeless love story that finds roots in the most unexpected way. With Gellar, Phillippe, Blair and Witherspoon, there isn’t a weak link among the cast that cohesively makes the movie so timeless.

Now, two decades since its theatrical debut, the film has inspired a successful musical that’s still running with the original cast having given their important seal of approval. There were multiple (less magical) sequels to follow as attempted spiritual successors and we were nearly granted an official sequel series with Gellar herself that was unfortunately passed on by NBC. (Big mistake!)

Regardless of the potential series that unfortunately never surfaced, there were still plenty of fans who were thrilled at the prospect of seeing more Cruel Intentions in any way possible. It’s very uncommon to see a film that focuses on young adults and still maintains its highly respected status. The impact it’s had on pop-culture is proof enough that Cruel Intentions is a story with power over audiences of all ages.

Are you celebrating the 20th anniversary of Cruel Intentions? The film is back in theaters for one week so make sure to check it out while you can!