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.

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.

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.