1999’s Cruel Intentions belongs in the same bracket as the epoch-defining Clueless, and 10 Things I Hate About You; modern retellings of classic literature that made accessibility the focus of their reinvention. Like the other two, Cruel Intentions goes for a school-age cast, though the school environment is less present, and the story instead focuses on a tight bubble of elite society where everyone is as rich as they are deceitful, and absolutely everyone seems right on the cusp of having sex with each other.

The story is a fairly straightforward thing that focuses on a web of deceit and manipulation woven by two New York step-siblings, played by Ryan Phillipe and Sarah Michelle Gellar. Based on Pierre Choderlos de Laclos’ 1782 novel Les Liaisons Dangereuses, the very ’90s retelling positions Gellar as the grand manipulator, and Phillipe as the destructive cad, who set out to destroy other people’s lives for the sake of sport, and because she was dumped.

With a screenplay and direction by Roger Kumble, Cruel Intentions is a Romance and Teen Drama film that stars Selma Blair, Sarah Michelle Gellar, Reese Witherspoon, and Ryan Phillippe. The plot revolves around a group of teens, with a man betting one of them that he can seduce a girl successfully.Director Roger Kumble Release Date March 5, 1999 Runtime 97 minutes

Alongside them, everyone else is pretty much a pawn in their game: particularly the virtuous (and celibate) high-achiever (Reese Witherspoon) and the air-headed school newcomer (Selma Blair) who become the subject of their wager. Modern sensibilities might not be quite as fond of Cruel Intentions as I or its army of contemporary fans were, and that will be tested tangibly with the release of Amazon’s new remake series. So what better time to dive back into Roger Kumble’s under-appreciated teen drama? Honestly, I’ll take any excuse I can.

Cruel Intentions’ Cast Is Excellent & Its Biggest Asset
Ryan Phillipe Is Cool, But Sarah Michelle Gellar And Selma Blair Are Brilliant

Rewatching Cruel Intentions now, I’m convinced Ryan Phillipe should have enjoyed a similar career trajectory to Leonardo DiCaprio, but it didn’t shake out that way for him. He made some great movies, all the same, but by 2005, he was making a Jason Statham/Wesley Snipes actioner as essentially the third billed actor despite being the main character. He’s not even on the DVD cover. Watching him as Sebastian, it’s impossible to see how that journey could be logical.

Phillipe is excellent as the Machiavellian Manhattanite, delightfully snearing, and exquisitely well-dressed. As a teenager, I saw him as an aspirational prototype (possibly not exactly what the movie was going for, I’ll concede), and a good deal of that came down to how much I liked his coat. 25 years on, the coat is still right up there (ranking second only to Jude Law’s in The Holiday, and pretty much every outfit in Guy Ritchie’s The Gentlemen). These are the important points of analysis you all need.

Cruel Intentions
spawned two sequels. Neither of which I can recommend in good conscience.

Alongside the cock-sure Phillipe, Sarah Michelle Gellar is a revelation as the very un-Buffy Kathryn, his step-sister and will-they-won’t-they lover. While Rachel McAdams’ Regina George became a sort of teen cultural touchstone 5 years later, Gellar’s performance here is the simmering prototype. Kathryn is abominable, and weaponizes her sexuality and her social influence in a way that will make modern younger audiences deeply uncomfortable. But she’s enormously good fun, and is almost a one-woman call-to-arms to bring back this subgenre of sexually aware storytelling.

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Reese Witherspoon and Selma Blair round out the main cast, with the former a virtual paragon of virtue, with Witherspoon playing her with the right blend of naivety and cynicism. Blair is a clownish delight as victim Cecile Caldwell, who becomes the pawn in a seedy game of vengeance orchestrated by Kathryn. She brings a sort of delirious, wide-eyed silliness that balances the sharper edges of the other characters, as well as the occasionally disarming reminder that everyone here isn’t old enough to vote.

For All Of Its Surface Gloss, Cruel Intentions Is Surprisingly Deep
The Story Is One Of Cruel Intentions’ Biggest Strengths… And It Holds Up

One of the most jarring things about rewatching Cruel Intentions in 2024 is the commentary on female sexuality, and how Kathryn has to play puppet master behind a respectable mask while Sebastian openly flaunts his “escapades”. The double standard is an interesting sidenote, and there’s definitely a message here about the power of sexuality, but it rather gives way to the fact that Kathryn is a monster.

Impressively, Cruel Intentions manages to make a cast of mostly thoroughly detestable characters – the coke-using preppy millionaires, the vapid airhead, the spiteful gay sidekick (wonderfully played by Joshua Jackson) – wholly charming. The whole thing is a pageant of falsehoods, which was always the best thing about Dangerous Liaisons (and the original French novel, of course), where everyone has the potential to be a backstabber, and even the most virtuous of people (including Witherspoon’s Annette and Sean Patrick Thomas’ music teacher Ronald) can quite easily be corrupted. All it takes is a little push.

The biggest problem for the new remake series of Cruel Intentions is how sexually provocative the original is. For more prudish generations, the extended kiss sequence between Kathryn and Cecile would be counted as unnecessary in its close-up glory; the step-sibling flirting may be too amoral; and the casual destruction of people’s lives might prove too spicy. I hope not, because they’re all things that made the original iconic, but were also just ornaments on a far more rewarding, rich story.

The subtle commentary on elitism is sprinkled on ever so gently.

The stakes are surprisingly high, even if the melodrama at the end gets a little silly. Phillipe’s performance struggles a touch as Sebastian begins to wrestle quite animatedly with his moral dilemma of whether he should be a good person, or he should have sex with his step-sister. But that’s sort of the point: Kathryn sets out on her terrorizing mission because she’s dumped, and has such disdain for everyone else that she doesn’t believe raining fire on everyone is a tad over-dramatic. Luckily, the film goes along with it, making it the audience’s responsibility to recognize the elements of farce.

In that analogy, you find the cleverest part of Cruel Intentions, which was largely overlooked at the time, because the idea of teenage identity was still not quite as pervasive or as understood in 1999 as it is now. In their world (our world, because I was a teenager when this movie tickled my synapses just right), everything is monumental, and no reaction is over-done. Again, the subtle commentary on elitism is sprinkled on ever so gently.

Cruel Intentions’ Soundtrack Still Slaps
Contemporary Music Has Rarely Been This Well Used

Look, sometimes the vernacular of your demographic is important, so you’ll have to forgive me that one. And it’s difficult to overstate just how great Cruel Intentions’ soundtrack is, or how well the song choices are integrated into scenes. The mighty Blur’s “Coffee & TV” backs the movie’s most famous scene (that should perhaps be “infamous”), and there are excellent needle drops for Placebo, Skunk Anansie, The Verve, and Counting Crows.

It’s the kind of soundtrack that you can – and indeed, I did – enjoy without the film playing, in a way that still enriches the scenes. That’s how well chosen the songs are for each individual moment. And there’s a very tuned-in musical identity on show here that is badly overlooked in modern movies. Perhaps it’s just that the songs are better?

Final Thoughts & Why You Should Still Watch Cruel Intentions In 2024

Cruel Intentions is still a high-camp, melodramatic joy that was perilously under-rated when it first came out. Looking at RottenTomatoes now, contemporary reviews slapped it with a 53% Rotten rating (compared to the far more accurate 80% audience score), and I still don’t know how. Picking through some of the reviews, the accusations of it being cynical and amoral rather fatally misunderstand the fact that that’s exactly what it’s supposed to be.

I started this review talking about Clueless and 10 Things I Hate About You – films ostensibly aimed at the same audience – but which were very, very different. Cruel Intentions is cooler, darker, more grown-up, and has more to say beyond the enduring power of love (though that is obviously a defining part of the story). Yes, it’s bitingly cynical, but so too is Dangerous Liaisons, and in 2024, there’s an even more pronounced parallel between its brand of elitism and the real world that makes it surprisingly relevant. That at least means the remake could stand to benefit from its contemporary rebrand.

ProsSarah Michelle Gellar and Selma Blair are phenomenal.The soundtrack is top tier.The story is mean, but delightfully irresistible.The aesthetic and vibes are immaculate. ConsThe melodrama towards the end gets a little much.