Cruel Intentions (1999) — The anti-Clueless

“You’re just a toy, Sebastian. A little toy I like to play with.”

Justin’s rating: It’s a bittersweet sin-phony

Justin’s review: If Clueless is at one end of the ’90s “rich teen” romcom spectrum, all full of giddy charm and bubbly fantasy, then Cruel Intentions has to sit right at the other end in the shadows with a skeevy grin. Both of these films made a strong impression upon many younger filmgoers in the ’90s, but perhaps this one should’ve been kept under lock and key.

Based on a 1782 French novel called Les Liaisons dangereuses, the basic setup looks at the depraved lives of an amoral wealthy class — in this case, just-barely-legal New York City teens at a rich prep school. Step-siblings Sebastian (Ryan Phillippe) and Kathryn (Sarah Michelle Gellar) expertly manipulate and mess with everyone around them, ruling the roost with their power, money, and sex appeal.

Bored and looking to up the stakes of competition, the pair make a bet whether or not Sebastian can bed the new headmaster’s daughter Annette (Reese Witherspoon). Additionally, there are plenty of other machinations in the works, and what a web they weave when first they practice to deceive.

In short, lives get wrecked, hearts are broken, and an unintentional romance is sparked. And yes, there may be a twist or two in the works, with karma coming for everyone with a vengeance.

Watching Cruel Intentions is a little like being sucked into a trashy soap opera, where you watch objectively bad people with a captive fascination. You don’t approve of their actions or character, but they are interesting — and you want to see if they’ll ever get theirs. Plus, there’s a sly streak of humor that keeps this from getting too dark and some not-too-subtle symbolism in the props, outfits, and even music choices.

And part of the enduring cultural stamp of Cruel Intentions is its compilation soundtrack — perhaps one of the all-time greatest of the ’90s. “Push It,” “Bittersweet Symphony,” “6 Underground,” “Lovefool,” “Praise You,” and so much more make this a must-own alt rock collection time capsule.

If this was an adult cast, I don’t think this would’ve blown up quite the way that it did (and they did that twice prior). Young actors delving into soap opera territory with a dash of romcom and a gut-punch ending made this a risque “must see” movie for the late-90s generation. Today, it’s seen as an immature relic and a subversive morality play combined — and, for better and probably worse, it became part of the zeitgeist of the decade.

For me, I’m not a fan despite its legendary status. It’s hard to watch movies with a whole cast of pretentious jerks be jerks to each other, and I hate the idea of this film being a role model to anyone. But I will keep a copy of the soundtrack in my collection, thank you.

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