By Chris Snellgrove | Updated
You don’t have to click on all those shady “what are you doing, stepbrother?” videos online to know that there is a strange and disturbing cultural fascination with this subject. This sounds like a very modern phenomenon, but it’s not: in fact, it was at the center of the raciest film of the ’90s, one that starred Sarah Michelle Gellar as someone who wanted to do the unthinkable.
This movie is Cruel intentions (1999), and if you’re ready to experience the raunchiest and most extreme film starring Buffy the Vampire Slayer, you can now stream this bizarre film on Prime Video.
What are you doing?
The incredibly steamy plot of Cruel intentions it’s that a young man wants to seduce a very good girl to win the most important prize of all: his half-sister. To succeed in this seduction, he will have to become a master manipulator who is not afraid to destroy the lives of several people to get what he wants. Once he develops feelings for the prim and proper girl he’s trying to deceive, it’s clear his life will never be the same.
The cast of Cruel intentions is full of surprises, including Ryan Phillippe (best known for Accident). He’s a rich teenager who’s tired of sleeping with women easily and sets himself a challenge: the girl (played by Reese Witherspoon, best known for Legally blonde) of her director, a girl who doesn’t believe in intimacy before love.
He has a bet with his half-sister (played by Buffy the Vampire Slayer icon Sarah Michelle Gellar), and if he wins, she will sleep with him. Along the way, he also finds time to corrupt a naive girl played by Selma Blair (best known for hell boy).
A crazy success at the box office
Compared to its modest budget of $10.5 million, Cruel intentions was a smash hit (about teenagers trying to break out), earning an outright $75.9 million at the box office. This led to two sequels, although both were direct-to-DVD disappointments. Interestingly, there was also a TV series planned for 2016 that never made it past the pilot stage and a TV series for 2024. Cruel intentions TV show that didn’t have enough staying power to last more than one season.
When Cruel intentions came out, professional reviewers didn’t know what to make of it. On Rotten Tomatoes, it has a 54 percent rating, with critics complaining that the film’s cast appeal wasn’t enough to make up for an uneven storyline and equally uneven performances.
Audiences disagreed, and the film notably has a Popcornmeter score of 80 percent. Movie fans in general have praised this movie for its provocative storytelling and steamy plot, and they generally agree on one important point: you shouldn’t try to watch this steamy movie when your parents are around!
Literary roots didn’t help cruel intentions
Even if Cruel intentions has major literary roots (it adapts the famous 1782 novel Dangerous Liaisons), its cultural cachet didn’t help the film win major awards, like an Oscar or a Golden Globe. Other accolades include two MTV Movie Awards (including Best Kiss for Sarah Michelle Gellar and Selma Blair’s kiss) and two Teen Choice Awards (including Choice Movie and, amusingly, Choice Movie Sleazebag for Gellar). These awards help to underline how popular this film was with the young audiences who enjoyed it, even if its raunchy subject matter left critics more than a little perplexed.
I was still in high school when Cruel intentions came out, and I was one of the young people blown away by its risky plot. At the time, I appreciated that the film was filled with so many pretty faces, including Sarah Michelle Gellar, the lead actress of Buffy the Vampire Slayer (one of my favorite shows). In this way, the film is rather meta, using its attractive stars to help sell a forbidden story in the same way that Ryan Phillippe’s character uses his good looks to fool people who really should know better.
Cruel intentions seen through a modern lens
Revisiting this film as an adult, I was struck by the quality of the plot. It’s easily overlooked among all the racy content. The character of Phillippe, for example, feels like a precursor to Barry Keoghan’s film. Salt burn character. Everyone is a master in the art of manipulation to get what they secretly want.
Cruel intentions has a lot to say about the intersection of desire and American Puritan culture. The storyline explores how dysfunctional it can be to reconcile one’s own desires with what society considers “normal.”
Would you agree that Cruel intentions Is it an entertaining adventure filled with great performances, or is it a film you’d like to put in the washing machine? Don’t be surprised if this decades-old film awakens something in you that you’ll never be able to put back to sleep.
