Sarah Catherine Hook and Zac Burgess, Cruel Intentions

Of all the movies that Amazon could have chosen to turn into a new series, Cruel Intentions may not have been one of more obvious options available. But that very spicy film left a big mark on those who came of age in the 1990s, and now, two decades, later, Prime Video is hoping for a similar result from a new series inspired by that erotic cult classic.

Both the original film and the upcoming show are based on the 18th century French novel Dangeous Liaisons, about the sexual machinations of certain members of the French aristocracy in the lead-up to the French Revolution. The film took the broad concepts of the novel — a rich man and woman using seduction as a tool of revenge — and turned it into a story of prep school step-siblings Kathryn and Sebastian (Sarah Michelle Gellar and Ryan Phillippe), who make a very peculiar bet. Sebastian claims he can seduce the closed-off daughter of the school headmaster (Reese Witherspoon), and if he does, Kathryn will have sex with him (eww).

While rebooting a random 1999 teen melodrama might seem a little weird on its face, never underestimate a streaming industry where originality takes a back seat to familiarity. Here's what we know about Prime Video's take on Cruel Intentions.

Cruel Intentions is slated to drop its premiere episode on Amazon Prime Video starting November 21, with the remainder of the episodes releasing weekly. Season 1 will consists of eight episodes.

Almost a month from its premiere date, Prime Video dropped the first trailer for the new series. It's got some references and Easter eggs to not just the original film, but also its not-so-well-remembered sequel, with the most obvious nod being a new cover of "Bittersweet Symphony," the song that's mostly remembered these days for its connection with Cruel Intentions. Check it out below.

In Prime Video's take, you can expect the broad strokes — the sexy bet, the step-sibling stuff, rich kids trying to maintain their status — but the particulars have been updated in a rather dramatic way. In the series, our focus will be on a pair of step-siblings, attending college in Washington, DC, who team up to seduce the vice president's daughter against the backdrop of the Greek system of fraternities and sororities.

One particular quirk of this new version of the story is that it's not a completely modern retelling of this story, as it will take place in a world without social media. This may be a bit of a screenwriting cheat, since the existence of Twitter, Instagram, TikTok and the like would obviously be a major complicating factor in a story like this one. Though when you consider the original novel took the form of a series of letters between characters, the more analog approach does make some sense for an adaptation.

Sarah Catherine Hook, Zac Burgess, Savannah Lee Smith

The series is created by Phoebe Fisher and Sara Goodman, who previously worked together on the canceled I Know What You Did Last Summer series for Prime Video.

The core cast is largely made up of young up-and-comers, including Sarah Catherine Hook and Zac Burgess as the villainous step-siblings. Sean Patrick Thomas, recently seen in The Boys spinoff Gen V, is the lone member of the original film's cast to return for this reboot. And the supporting cast includes a few secret weapons: Claire Forlani (who replaces Laura Benanti, who exited in 2023 over scheduling conflicts), Jon Tenney, and recent Tony nominee Nikki Crawford.

The 1999 Cruel Intentions movie is available to watch for free with ads on Amazon's FreeVee service.