Good news, silly rabbit: A new generation is finally getting its own version of Cruel Intentions, thanks to a rebooted Prime Video series. But judging by the just-unveiled first trailer that features everything from a cover of “Bittersweet Symphony” to a black convertible, there will be Easter eggs aplenty for fans of the original 1999 film as well.

Need a refresher—or an introduction? Before Euphoria, Riverdale, Gossip Girl, Mean Girls and even The Real Housewives of New York, there was Cruel Intentions. A contemporary retelling of Pierre Choderlos de Laclos’s classic book Les Liaisons Dangereuses with a prep-school setting, the movie starred a raven-haired Sarah Michelle Gellar as an Upper East Side queen bee named Kathryn Merteuil, who challenges her hookup buddy/stepbrother Sebastian Valmont (Ryan Phillippe) to bed the new school headmaster’s virginal daughter, Annette Hargrove (Reese Witherspoon).

Released in March 1999 amid a millennial teen boom that also included She’s All That, 10 Things I Hate About You, Never Been Kissed and Varsity Blues, Cruel Intentions stood out from the pack as it delivered on the promise of its tantalizing title. And while the slick flick may not land on any official Best Movies lists, it remains a smart, seductive and sexy classic.

So what’s on tap for the new Cruel Intentions? Grab an iced tea from Long Island, and read on to find out exactly what to expect.

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How can I watch Cruel Intentions the series?

Starting Nov. 21, all eight episodes of the series will be available to stream on Prime Video—one of the cool benefits of an Amazon Prime membership. Each installment of Cruel Intentions will be available to download and watch later too.

FYI, you can also queue up the Sarah Michelle Gellar movie on Prime Video.

What is the Cruel Intentions TV series about?

Farewell, Upper East Side and wildly inappropriate high schoolers. This Cruel Intentions iteration is set at Manchester College, a fictional university in Washington D.C. That’s where affluent stepsiblings Caroline Merteuil (Sarah Catherine Hook from the Netflix series First Kill) and Lucien Valmont (Australian actor Zac Burgess) rule their school’s Greek system. After a brutal hazing scandal threatens to shut down all fraternity and sorority life on campus, Caroline enlists Lucien’s help to seduce the U.S. vice president’s daughter, Annie (Savannah Lee Smith), and convince the student to pledge her sorority.

“We talked a lot about what the peek behind the curtain of a rarefied world that we hadn’t seen before could be, where it felt like it had its own social hierarchy,” says Phoebe Fisher, who adapted the series with Sara Goodman. (The duo previously worked together on the I Know What You Did Last Summer TV series.)

New storyline aside, which you’ll get a peek at in the brand-new trailer, get ready for nostalgic callbacks in terms of images and an overall sultry vibe. The trailer previews a pool scene between two of the show’s leads reminiscent of when Witherspoon’s Annette swims with Phillippe’s bad-boy heartbreaker. There’s also a “practice kiss” make-out scene, similar to the iconic image of Gellar and Selma Blair’s naive Cece Caldwell locking lips on the Central Park lawn.

Plus! Sean Patrick Thomas, who appeared as love-struck cello teacher Ronald Clifford in the film, now plays Professor Hank Chadwick at Manchester.

Cruel Intentions on Prime Video.Courtesy Prime Video

What’s the story behind the music?

The original movie soundtrack was incredible. The Verve’s haunting ballad “Bittersweet Symphony” originally charted in 1997, but it became immortalized via Cruel Intentions‘s shocking closing montage. (Never mind that a sunglasses-wearing Annette cruises in Sebastian’s convertible with mountains in the background, even though she’s supposed to be in New York City!) Sure enough, the trailer for the new Cruel Intentions kicks off with a female-fronted cover of the song.

Here’s hoping the series also pays homage to the film’s other memorable (and admittedly very ’90s) tracks, including Fatboy Slim’s “Praise You,” Blur’s “Coffee & TV” and the Counting Crows’s “Colorblind.” That last song was highlighted in a scene that showed firsthand why Phillippe and Witherspoon fell in love offscreen and got married.

Will there be a Season 2 of Cruel Intentions?

That’s unclear for now. Of course, Prime Video will want to see just how this new incarnation of the series does before officially green-lighting a second season.

And this isn’t the first attempt at reboot. The obscure direct-to-video 2000 sequel was actually a prequel that chronicled Sebastian as a young teen playboy. But the 2015 NBC pilot—which failed to get picked up to a series—would have taken place more than 15 years after the film left off, with Gellar’s Kathryn vying for control of Valmont International. Perhaps it’s a Season 2 blueprint?

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At Reader’s Digest, we’re committed to producing high-quality content by writers with expertise and experience in their field in consultation with relevant, qualified experts. We rely on reputable primary sources, including government and professional organizations and academic institutions as well as our writers’ personal experiences where appropriate. We verify all facts and data, back them with credible sourcing and revisit them over time to ensure they remain accurate and up to date. For this story on the new Cruel Intentions series, Mara Reinstein tapped her two decades of experience as an entertainment journalist, film critic and pop culture expert. Read more about our team, our contributors and our editorial policies.

Sources:

  • Official Trailer: Cruel Intentions
  • Entertainment Weekly: “Cruel Intentions exclusive first-look photos take you inside Greek life”
  • The Hollywood Reporter: “Amazon’s ‘Cruel Intentions’ Series Gets First Trailer, Release Date”
  • Billboard: “The Verve’s ‘Bitter Sweet Symphony’ Returns to Charts After Songwriting Dispute Resolved”
  • Deadline: “Why Sarah Michelle Gellar Is ‘Grateful’ NBC Didn’t Pick Up The ‘Cruel Intentions’ Reboot”