Cruel Intentions is Dangerous Liaisons in a Manhattan prep school, with Sarah Michelle Gellar and Ryan Phillippe as step-siblings who treat seduction as a competitive sport. It is glossy, mean, and completely sincere about the wreckage two bored rich kids can cause when they turn other people's hearts into a wager. The soundtrack and the marble staircases did the rest.
The films below run on the same current: desire used as a weapon and a beautiful surface stretched over something colder. Some are set in high schools, some among adults who never grew out of the games, and one is the doomed teenage tragedy the whole genre keeps rewriting.

Romeo + Juliet

Baz Luhrmann fires Shakespeare through a music-video cannon: Verona Beach, guns instead of swords, Leonardo DiCaprio and Claire Danes falling in love across a fish tank. The language stays four hundred years old while everything around it screams 1996.
It is the doomed romance Cruel Intentions is quietly built on, the story of young love wrecked by the cruelty of the people around it. Both films are gorgeous and heightened to the edge of camp, and both know that a beautiful surface makes the tragedy underneath hit harder.
The Virgin Suicides

Sofia Coppola's debut watches five sisters in 1970s suburbia from the outside, through the eyes of the neighborhood boys who are obsessed with them and never really know them. It is hazy, sun-bleached, and quietly devastating.
Like Cruel Intentions, it turns on desire aimed at girls treated as prizes rather than people, and on how badly the people watching them fail them. It is dreamy where the other is sharp, but the ache underneath is exactly the same.
Girl, Interrupted

Winona Ryder checks into a 1960s psychiatric hospital and gets pulled into the orbit of Angelina Jolie's magnetic, dangerous Lisa, in an adaptation of Susanna Kaysen's memoir. It is about young women pushing against the roles the world hands them.
It shares Cruel Intentions' interest in a charismatic manipulator who is impossible to look away from, and in privileged kids testing how much damage they can do. Jolie's Lisa and Gellar's Kathryn are cousins: both perform danger so well that everyone around them mistakes it for freedom.
The Dreamers

Bernardo Bertolucci drops an American student into 1968 Paris and a strange, intimate game with a French brother and sister who never quite let anyone else in. It is sensual, cinephile, and unashamed of its own transgressions.
Cruel Intentions and this both circle a closed pair of privileged young people who turn outsiders into pieces in their private games. The charge is the same in both: closeness and manipulation braided together until you can't separate them.
Closer

Mike Nichols lines up four Londoners (Natalie Portman, Jude Law, Julia Roberts, Clive Owen) and lets them wound each other over years, with dialogue sharp enough to draw blood. It is a chamber piece about attraction and betrayal with no soft edges.
This is Cruel Intentions grown up and stripped of the prep-school gloss: the same belief that desire and cruelty run on the same wiring. Both films watch attractive people use honesty as a weapon and treat love as a game they intend to win, whatever it costs the other player.
Eyes Wide Shut

Kubrick's last film sends a married doctor (Tom Cruise) on a long nocturnal drift through jealousy, temptation, and a masked secret society, after his wife (Nicole Kidman) confesses a fantasy. It is slow, dreamlike, and deeply unsettling about desire.
Cruel Intentions and this both treat sex as a matter of power and performance rather than warmth. The class and the secrecy line up too: beautiful people moving through gilded rooms where wanting someone is a move in a larger game, and where nobody is quite telling the truth.
Match Point

Woody Allen swaps comedy for cold tragedy: a social-climbing tennis pro marries into a wealthy London family and starts a dangerous affair with his brother-in-law's fiancée (Scarlett Johansson). The film is obsessed with luck and getting away with things.
It shares Cruel Intentions' clear-eyed cynicism about desire and ambition wearing the same face. Both stories put beautiful, calculating people inside gorgeous rooms and ask how far they will go to get what they want, and how little guilt actually slows them down.
Mean Girls

Tina Fey's high-school comedy turns teenage social warfare into a precise, quotable science, as new girl Cady infiltrates the most popular clique and slowly becomes what she meant to expose. It is funnier than Cruel Intentions and just as sharp about cruelty.
Both films understand that popularity is a game with rules, players, and casualties, run by someone who is very good at it and enjoys it too much. Regina George and Kathryn Merteuil would recognize each other instantly, and neither would blink.
The Talented Mr. Ripley

Anthony Minghella sends Tom Ripley (Matt Damon), a nobody with a gift for imitation, into the golden world of a rich American playboy (Jude Law) in 1950s Italy, where he starts wanting the life more than he can bear to leave it. It is gorgeous, sunlit, and quietly monstrous.
Ripley and Kathryn Merteuil are the same animal: a charming manipulator moving through privilege they were not born into, treating desire and friendship as tools. Both films are cold underneath the beauty, and both understand how far a person will go once wanting something curdles into needing to own it.
Dangerous Liaisons

Here is the original, in powdered wigs. Stephen Frears films Choderlos de Laclos's 18th-century novel as a duel between two aristocrats, the Marquise de Merteuil (Glenn Close) and the Vicomte de Valmont (John Malkovich), who wager on seductions the way other people bet on cards.
Cruel Intentions is a direct, uncredited remake of this, right down to the names. Everything the teen version does, this did first: seduction as warfare, love mistaken for a game, and two brilliant people who cannot stop playing even when it starts to cost them. A fitting place to end, since it is where the whole story began.
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