One of the rare instances where an adaptation or remake of source material gains a life of its own. Much like how 10 Things I Hate About You went on to have a life beyond being just an adaptation of The Taming of the Shrew, Cruel Intentions built its own legacy. This adaptation has a straight-to-video sequel that started as a FOX pilot, a stage musical, and now even a recent Amazon series. Roger Kumble’s sexy teen drama from 1999 still can put it wherever it wants.

For anyone who somehow doesn’t know, Cruel Intentions is a modern take on Dangerous Liaisons, which itself came from the French novel Les Liaisons dangereuses by Pierre Choderlos de Laclos. Instead of aristocrats playing manipulative social games in 18th century France, this version drops all of that into wealthy late 90s New York teenagers and lets them go to work. It turns out manipulation, seduction, and terrible people making bad choices travel through time pretty well.

The plot centers around Sebastian Valmont and Kathryn Merteuil, two rich and very bored step-siblings who treat people’s lives and emotions like a competitive sport. Kathryn challenges Sebastian to seduce Annette Hargrove, the daughter of their school’s new headmaster and a girl known for wanting to wait for love and commitment. Naturally, what starts as just another game gets messier as feelings get involved and the walls around Sebastian begin to crack.

I have nostalgia problems. I often revisit films from a certain time period and they still work for me. Do I think this is the greatest film ever, or some movie unfairly denied Oscar nominations? No. But 1999 was a huge year for teen films, and Cruel Intentions was a standout. Teen movies were everywhere at that point, but a lot of them felt like they were chasing the same audience in different ways. Cruel Intentions had a different edge to it. It leaned harder into manipulation, sex, and cruelty, while still somehow wrapping itself in glossy soap opera energy that made it easy to get swept up in.

I’ve seen it numerous times, and watching it again with audio description was just another notch in the delicious belt. Ryan Phillippe is perfect as Sebastian, playing the charming bad boy role effortlessly, and Sarah Michelle Gellar makes a great Kathryn. She gets some of the film’s best moments and clearly enjoys every second of being terrible. Reese Witherspoon is fun as the nice girl caught in the middle of their games, and the supporting cast, from Selma Blair and Joshua Jackson to adults like Christine Baranski, really helps make this a successful ensemble.

There are definitely parts of this that scream late 90s time capsule now, but that is part of the charm. Some movies age and become museum pieces. This one still feels like it knows exactly what kind of movie it wants to be.

This is still a very delicious guilty pleasure 25 years later.

Fresh: 8.4/10