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The turn-of-the-century holds down a special spot in pop culture and Hollywood’s big screen. Some of the most popular movies remain hits, especially those aimed at teens. Amongst the list of ’90s classics was, of course, Cruel Intentions. The 1999 movie was so well-received that a sequel was set in motion. But Cruel Intentions 2 was really supposed to be a TV show.

‘Cruel Intentions’ was a breakout hit

cruel intentions 2
(L-R): Reese Witherspoon and Sarah Michelle Gellar in a scene from the film ‘Cruel Intentions’, 1999. | Columbia Pictures/Getty Images

Cruel Intentions had it all. From malicious and manipulative step-siblings to surprising sexual schemes, audiences couldn’t get enough of the R-rated film. Not to mention, the cast of Cruel Intentions was an absolute powerhouse. 

Sarah Michelle Gellar, Christine Baranski, Joshua Jackson, and Ryan Phillippe starred in the sultry production. Plus, playing the part of Annette Hargrove was no other than Reese Witherspoon (though Katie Holmes nearly landed the role). 

In addition to winning an award for that kiss, Cruel Intentions performed spectacularly at the box office. Due to its success, the studio — naturally — wanted to capitalize on this.

‘Cruel Intentions 2’ was actually just 2 TV episodes packaged together

Unfortunately, the sequel wasn’t meant to be a massive hit. There were many different reasons why many thought Cruel Intentions 2 fell short, but, one of the main ones was that the film was actually intended to be a television series. Variety revealed the details behind how it all went down. 

The path behind the sequel — actually a prequel — for Cruel Intentions was not an easy or clear one. Originally titled Manchester Prep, it was pitched and developed at Fox. 

Cruel Intentions premiered in March 1999. Just a few months later, the filming and work for Manchester Prep were in full swing. However, the set was abruptly shut down after filming just two episodes. 

From the start, Fox was concerned about the series’ “edgy content.” And apparently, when previews began to roll out, Rupert Murdoch, head of News Corp., was “outraged.” With just the pilot and one other episode completed, they pulled the plug on the show.

These unusual circumstances are what led this TV series to the film format. Serving as a bit of an origin story, the movie revolved around Kathryn and Sebastian’s earlier days and their love to torture their peers. It didn’t feature any of the original actors, though. But Amy Adams did star in the direct-to-video release.

‘Cruel Intentions 3’ and the legacy behind the films 

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Despite its failure, the attempts didn’t stop with Cruel Intentions 2. A third film, Cruel Intentions 3, debuted in 2004, featuring all-new characters. (It also flopped). Then in 2015, NBC attempted a new angle on the franchise — a sequel TV series, with Gellar set to return. However, it never took off.

One avenue that did prove successful? A jukebox musical. Cruel Intentions: The ’90s Musical debuted in 2015, later having an Off-Broadway run in 2017. The musical also toured, and it featured well-known actors like Katie Stevens of The Bold Type, Pretty Little Liars‘ Janel Parrish, and Frankie Grande.