Long before Gossip Girl depicted a scandalous world centered around Manhattan’s prep school elite, there was Cruel Intentions, the 1999 film starring Sarah Michelle Gellar, Reese Witherspoon, and Ryan Phillippe. The movie, which was released exactly 20 years ago today on March 5th, 1999, is about a pair of rich, manipulative, and very horny step-siblings named Sebastian and Kathryn (played by Phillippe and Gellar), who pass time by exploiting other people and destroying their lives as if it were a sport. Cruel Intentions may have received a mixed response from critics at the time of its release, but anyone would agree it produced many memorable moments, such as the kiss between Kathryn and Cecile (Selma Blair), Sebastian’s “burn book,” Kathryn’s secret coke rosary, and the song “Bittersweet Symphony” by The Verve playing over the film’s dramatic final scene.
Following a trend of ‘90s teen movies inspired by old books—She’s All That by Pygmalion, 10 Things I Hate About You by Shakespeare’s The Taming of the Shrew, and Clueless by Jane Austen’s Emma—Cruel Intentions was based on the salacious 1782 French novel Les Liaisons dangereuses. Motivated by sex, revenge, and, simply, boredom, Sebastian and Kathryn make a wager with each other using two other students, Annette (Witherspoon) and Cecile, as pawns. If Sebastian successfully seduces proud virgin Annette, he is able to fulfill his longtime desire of boning Kathryn (yes, his step-sister). If he loses, Kathryn gets the pink slip to his vintage sports car.
Sebastian could be described by many who remember the movie as their first problematic crush, though “problematic” is an extremely mild word to describe the character’s conniving, Machiavellian behavior. Still, many of us can never forget the moment (and might even have swooned) when Sebastian is waiting for Annette at the top of the Penn station escalator, confessing that he has fallen in love with her. The characters of Cruel Intentions were ones we loved to hate, hated to love, and hoped to never meet in real life.
Though Cruel Intentions came out in 1999, the same year as She’s All That, Jawbreaker, and Drive Me Crazy, among many others, the fashion in the film is not typical of ‘90s teen movie style. Instead of embodying a Cher Horowitz from Clueless influence with candy-colored cardigans and miniskirts, Gellar’s HBIC wears power blazers and lingerie-inspired garb, channeling Madonna circa “Express Yourself.”
Sebastian and Kathryn wore sophisticated clothing in dark colors, while Annette gravitated towards lighter shades, a play to her innocence. “I wanted each character to be different, and every actor has their own ideas,” the film’s costume designer, Denise Wingate, tells HelloGiggles, adding that Gellar was “fully on board” when it came to curating looks for her character. “She knew exactly what looked good on her, and was game for going shopping, having fittings, and [how we paired] that Dolce and Gabbana suit at the beginning of the movie. We made the corset and added that to it and put in the bustier.”
For Annette’s wardrobe, they went with lighter colors. “We really wanted her to look a little more conservative,” Wingate explains. “A little more tonally, with the pastels, and just have her look sweeter. And then Cecile was just kind of loopy. But [Blair] was also a really good sport and would go with anything. The koala T-shirt was really funny.”
Out of the movie’s entire wardrobe, Cecile’s koala shirt, which was in the script, seems like it would be the piece most likely to be thrifted, but it was actually custom-made for legal reasons. “We were afraid we weren’t going to get clearance,” Wingate says. “I think our art department made something up and created it. We had a bunch of different ideas and that was the one that we picked because it was so silly. When you’re watching [the scene], the room and costumes are so opulent, and then Cecile comes in with this little koala T-shirt, and it looks so stupid. And then the punchline, ‘How are things down under?’ It just worked.”
For the costumes, Wingate sourced a mix of high-end clothing from Barney’s and less expensive pieces from J.Crew, along with tapping into Phillippe’s Prada hookup and a few vintage items. “We just kind of mixed it all together and we made some things,” Wingate says. “I was really proud of a long, black, frock coat we made for Ryan because I used a sample from an 18th-century riding coat from a costume house. We took that idea and that shape, and then made one that was long and had burgundy silk lining. We just tried to take silhouettes from a different period and incorporate them into contemporary looks.”
During the famous kiss scene between Kathryn and Cecile in the park, there’s an obvious sartorial distinction between the two characters. Annette is wearing a bright pink top and coordinating plaid skirt with a green sweater tied, preppy-style, around her neck, whereas Kathryn, dressed in head-to-toe black, looks like she’s going to a funeral. “I had pulled up images of Audrey Hepburn, and so we really tried to emulate that,” Wingate says. “Sometimes I have all these ideas and visions and either people will say, ‘That’s ridiculous,’ or, ‘That’s completely crazy, and let’s do it.’ And Sarah was like, ‘That’s completely crazy, let’s do it.’” Wingate points out how the tantalizing scene was shot in the middle of crowded Central Park. “There were people everywhere, and they were so ballsy by just going for [the kiss]. I thought it was fantastic,” she recalls.
As for that iconic cocaine rosary? It was the work of prop master Linda Reiss. “I did a lot of reference into rosaries, crucifixes, and period jewelry that would hold poison or perfume,” Reiss tells HelloGiggles. “I then sort of combined the concept, and sketched out the idea for Roger Kumble [the director] and had a jeweler make the rosary.” Reiss used dark blue sapphire-like stones and black freshwater pearls for the piece, as a throwback to the period jewelry she researched. And if you’re wondering what was used for the coke, Reiss says it’s usually powdered lactose, but if the person is lactose-intolerant, ground-up homeopathic arnica tablets are used instead. Another important prop to the film’s plot was Sebastian’s diary, which Reiss says was inspired by Italian leather journals. “Ryan Phillippe did much of the writing inside himself,” she adds.
Ultimately, it was important for Wingate to have the costumes transcend time. “If you were making that movie now, everyone would have smartphones. And they didn’t have that, which is great. It keeps it kind of fresh. You don’t really know what decade it’s from.” Wingate also did the costumes for She’s All That, working on it immediately after Cruel Intentions, and notes how vastly different the two movies are in terms of the costumes. “The difference with She’s All That was that the fashion was really specific to that time, just like Clueless. They both look of the time, and Cruel Intentions does not.”
However, she says the two films do have something in common. “Looking back, both of those movies were very female-empowering,” Wingate says. “The guys seem to be catalysts, but they’re not the stars. The women were really strong characters, and I think those movies can still hold up today with where we’re at politically.”
To celebrate the 20th anniversary, Cruel Intentions will be re-released in theaters nationwide starting March 22nd.