2694. Cruel Intentions (1999)

Starring: Sarah Michelle Gellar, Ryan Phillippe, Reese Witherspoon

Director: Roger Kumble

Running Time: 97 mins

Cruel Intentions is an American film about two wealthy high school students who hatch plans to destroy a former lover, deflower the virgin daughter of their school’s incoming headmaster, all the while facing up to the realities of their own reputations.

While it may not quite hit home with its critique of high school culture and the ferocity of some, there’s something unforgettably striking about Cruel Intentions. It’s a film that, no matter how dark and mean-spirited it may seem, never lets up, and in tandem with an elegant and exciting visual style, it’s certainly one of the bolder films you’ll see.

Let’s start on that point, because although I wasn’t taken aback by the story here, Cruel Intentions has a unique and excitingly dark atmosphere throughout. Following the cruel machinations of two wealthy students with long-standing reputations, the film is at its most exciting when it’s at its nastiest.

As a narrative piece, there are more than a few moments that are morally repugnant to watch unfold, but because director Roger Kumble injects the film with such a boldly dark and sinister atmosphere, relishing the evil schemes of two awful human beings, there’s a point where you too become strangely drawn into this world of toxic and nasty planning.

Whether it be the film’s tendencies to stray towards X-rated drama or its main characters’ relentless capacity for evil, there’s always something about Cruel Intentions that leaves you on the edge of your seat, biting your nails as you wonder whether it will actually push the boat out even further.

Couple all that with some fantastically dastardly lead performances from Sarah Michelle Gellar and Ryan Phillippe, as well as a very clever turn from Reese Witherspoon, and you have a film that’s filled to the brim with dark intrigue and some really striking tension throughout.

And finally, I have to say a word on the soundtrack here. In keeping with the film’s ice cool yet theatrically dark atmosphere, Cruel Intentions thrills with an exhilarating contemporary soundtrack, featuring numerous classics from the late 1990s that fit in perfectly every time. Not only does that music add style in heaps and bounds, but is also so sharp and modern that it brings the same sense of excitement as the film’s darkest moments – a real standout feature of the movie.

Having said all that, Cruel Intentions doesn’t quite live up to its unforgettable style and boldness when it comes to its story. As I said earlier, it’s most exciting at its darkest moments, but the plot unfortunately isn’t a consistent thrill ride into the depths of despair.

Instead, while it absolutely sticks to its guns with increasingly striking twists, its core plot just doesn’t follow the same existing exhilarating mentality, unfortunately taking a look at the reputations of its two main characters and modern high school culture in general with a disappointingly hopeful perspective.

That may sound very pessimistic, but I was so thrilled by Cruel Intentions when it was showing the darkest sides of humanity, that its more optimistic moments unfortunately don’t feel like they cut the mustard, and as if they’ve taken the place of something darker that could have been so much more memorable.

Of course, the movie is based off the classic story Dangerous Liaisons, but I felt that Cruel Intentions, at its most positive, went just a little too far, and didn’t help to provide the existing exhilarating rollercoaster descent into pure darkness that I was so impressed by at first.

Overall, then, there’s no denying that Cruel Intentions is a memorable film. Stylish, bold, intriguing and often exhilaratingly dark, the film is hugely impressive as it shows you the nastiest sides of humanity, only missing out on really hitting home with a less-than-exhilarating narrative that both misses the mark on the film’s core themes, and just isn’t as strikingly dark as those most impressive moments, which is why I’m giving it a 7.4.