All these youngins out there think that Gossip Girl was our first look into the salacious lives of rich and morally bankrupt teens living in New York City but 20 years ago a little movie called Cruel Intentions gave us a darkly comedic glimpse into teen excess and kids behaving badly. The film is part of the Class of 1999 teen films that includes the likes of She’s All That, 10 Things I Hate About You, and Varsity Blues. What sets it apart from its other upperclassmen is that it didn’t exactly play it safe. By today’s standards, the R-rated Cruel Intentions is pretty tame but in 1999 you definitely didn’t see your favorite teen movie stars of the moment explicitly talking about sex and reveling in all things wicked and deceitful. Cruel Intentions was definitely the dirty member of the Class of ’99 and while it may lack the heart of some of its counterparts, it definitely has more bite and that’s why it still packs a wickedly satisfying punch 20 years later.
Cruel Intentions actually began its life under the working title, Cruel Inventions. Many of the performers in the film vividly recall doing the table read with that as the working title but it’s hard to imagine the film being called anything else at this point. The film is based on the 1782 novel ‘Les Liaisons Dangereuses‘ which has been adapted on two other occasions before the modern day teen approach was taken on. The first, and probably most well-known, is 1988’s Dangerous Liaisons which stars Glenn Close, John Malkovich, Michelle Pfeiffer, Swoosie Kurtz, Keanu Reeves, and Uma Thurman. The film received generally positive reviews from critics with major praise drawn towards Close and Pfeiffer’s performances, screenplay, production values, and costumes. At the 61st Academy Awards, the film received seven Oscar nominations, including Best Picture and it ended up winning three for Best Adapted Screenplay, Best Costume Design, and Best Production Design. The next adaptation was 1989’s Valmont which starred Colin Firth, Annette Bening, and Meg Tilly. The film wasn’t as well received as Dangerous Liaisons and only received a limited run in theaters before it faded away.
The difference between Cruel Intentions and the other adaptations is that it made the main characters teenagers and it swapped France for New York in a 20th-century retelling of sexual mind games and betrayal. Teen films during the 90s often took classic literary pieces and updated them for a modern audience. 10 Things I Hate About You did it with William Shakespeare’s “The Taming of the Shrew” while She’s All That drew its inspiration from George Bernard Shaw’s “Pygmalion.” It’s a testament to some of those works that they are so easily translated to modern times and good writers were able to take some of those more classic elements and spin them into a world of teenage politics that was relatable and didn’t speak down to its target audience.
Director and writer Roger Kumble takes a lot of the more classic elements from the source material and makes it an instantly alluring sexual cat and mouse game between Kathryn Merteuli (Sarah Michelle Gellar) and Sebastian Valmont (Ryan Phillippe). The pair are bored, rich and void of any adult supervision. They are step-siblings who get great joy out deceiving everyone around them while also embracing the lurid fun of destroying lives and engaging in activity that would make any adult cringe. Sebastian doesn’t quite hide his bad boy persona. It’s pretty much known that he’s a deviant but he’s rich and comes from privilege so, while he has a rep, he’s still the kind of guy you may secretly long to be. Kathryn is a beast of a different nature. She’s probably even more cunning and wicked than Sebastian but she has to put on appearances that she’s a good girl. She’s student body president and in her words “has to act like Mary Sunshine 24/7 just so people think she’s a lady.” Kathryn and Sebastian haven’t engaged in sex but it’s clear he wants to and very clear that she enjoys teasing him with the notion that it could happen.
Like any good teen film, and apparently, any good piece of classic literary fiction, the plot device of the film involves a bet. Annette Hargrove (Reese Witherspoon) is new to Manchester Prep and has just written a piece for Seventeen magazine about her desire to wait to have sex until she’s married and in love. Kathryn has her sights set on destroying a new student named Cecile Caldwell. Kathryn’s ex, Court Reynolds (Charlie O’Connell) dumped Kathryn for Cecile and she has taken on the newbie in the guise of friendship but in reality, she wants to secretly destroy her. Kathryn would like Sebastian’s help to do so but he finds deflowering the virginal Annette more of a challenge. While the plot to destroy Cecile is in play, Kathryn doesn’t think Sebastian has what it takes to seduce Annette and thus a wager is born between the two. If Sebastian can’t seduce Annette, she gets his prized 1956 Jaguar Roadster and if he succeeds, he’ll get to sleep with Kathryn. Just to show you how “dirty” this all was in 1999, Sebastian initially isn’t too interested until Kathryn informs him “he can put it anywhere.” Yep, not the average dialogue you were hearing from stars featured on The WB.
The performers inhabiting this world of teen sex and drugs were all sort of breaking new ground at the time. In the role of Kathryn, Sarah Michelle Gellar had once played a wicked character on the soap All My Children but you’d only really know that if you were my mom. Back in 1999, Buffy the Vampire Slayer was in the middle of its third season and was one of the biggest hits on The WB. Prior to that, Gellar was very much a part of the teen horror movie clique after appearing in hit films such as I Know What You Did Last Summer and Scream 2. If you were a fan of hers during this time period, Cruel Intentions was a major departure from her normal roles and it’s definitely a role of hers that still stands out 20 years later. She’s charming, wonderfully evil and looks like she’s relishing every single moment of debauchery she’s engaging in. After seeing the film for the first time, I recall friends saying that she went from Buffy blonde to bitch brunette and we loved every single second of it.
The male lead also had a connection to Sarah Michelle Gellar having played her boyfriend in I Know What You Did Last Summer. Ryan Phillippe, at the time, also didn’t display he could play someone so cunning. Sure, Barry in Summer is an asshole but Sebastian is a totally different breed entirely. He also has immense fun in the role and most importantly, he shares potent chemistry with Sarah Michelle Gellar that makes some of their scenes a joy to watch. The film is honestly at its best when they’re sparring with each other in a game of who is actually in control of the situation.
In the role of Annette, Reese Witherspoon probably had the highest pedigree. The other performers were probably more well-known but Witherspoon had wowed critics in the film Freeway back in 1996 and the year before Cruel Intentions she was in the critically acclaimed Pleasantville. There was a sense that Reese Witherspoon had more in her that would make her more than an actress who would appear in the teen movie of the moment. This is not a detriment to anyone else’s talent but sometimes you can tell when people are going places and Witherspoon was definitely one of those actresses. Another added component, that really adds to her scenes with Phillippe, is that they were dating at the time so their effortless chemistry is very natural. There is a scene later in the film where he has to tell her she was just a conquest and that he didn’t care about her and Phillippe actually got physically ill after doing it because he had to be so hurtful to her. They ended up marrying each other later that year but would subsequently divorce in 2007.
Rounding out the supporting cast is Selma Blair as Cecile who hadn’t really had a lot of credits to her name that people would know at the time but Blair revealed in a recent Instagram post that Sarah Michelle Gellar fought hard for her with Roger Kumble so that she would be cast in the film and she definitely is a comedic highlight that steals several of her scenes. Blair auditioned in character and deliberately made Cecile, originally a victimized waif in the source material, a more comedic and sexually aggressive presence in the film, undermining the potentially ghoulish corruption Kathryn and Sebastian attempt to enact on her. Blair’s star really grew after this in such films as Legally Blonde (with Reese Witherspoon) and The Sweetest Thing (directed by Roger Kumble).
Also on deck is Sean Patrick Thomas as Ronald, a naive pawn being played to seduce Cecile in order for her to get the riot act from her mom (played wonderfully by Christine Baranski). This was also one of his first mainstream roles and he also benefitted from its success in turns like Save the Last Dance.
The best thing that can be said about the casting overall is that in an era where even the best young adult actors were usually found playing stock roles such as The Bitchy Prom Queen or The Handsome Jock in between their tenures on teen television, Cruel Intentions offered rising stars an opportunity to prove their range. Joshua Jackson, then two seasons into his role as James Van Der Beek’s BFF Pacey Witter on Dawson’s Creek, pulls off a bleached-blonde dye job as one of Sebastian’s gay accomplices in sexual blackmail, while there’s also a fun cameo from Tara Reid. Watching the modern-day tabloid magnet and former Celebrity Big Brother contestant play a wholesome good girl unexpectedly dropped into a scandal is, in retrospect, hilarious.
Perhaps what makes Cruel Intentions so enduring is its reckless abandon; it’s a walk on the wild side, the kind of film that you didn’t want your parents to know you had seen because you were most likely too young upon your first viewing. It made you wonder are kids really doing this in high school? Am I missing out? Is it just a New York thing? Whatever it was, the situations were all so lurid and distasteful but damn it sure looked fun. The film unapologetic in its sexuality and, much like the characters themselves, we wait for shit to hit the fan as everyone gets what’s coming to them. There wasn’t really anything like it at the time and I would argue that most projects involving rich teens behaving badly probably took a cue from Cruel Intentions in some shape or form. A perfect example would be the film’s ending, which builds to a bewilderingly brilliant final scene accompanied by The Verve’s Bitter Sweet Symphony. It can be argued that Kathryn’s takedown via Sebastian’s journal could’ve been an inspiration for the “Burn Book” in 2004’s Mean Girls.
Cruel Intentions was the next major teen film to be released after the success of She’s All That in February of 1999. Opening on March 5, 1999, the film, budgeted at just $10.5 million, opened in second place behind Analyze This with $13 million, turning a profit after its opening weekend. The film ultimately grossed $38.2 million at the domestic box office and $75.9 million worldwide, making it a box office hit. I would even argue that it achieved even larger cult status when it was released on home video and is probably why it continues to endure even today.
Critics were mixed on Cruel Intentions as it holds a 49% rotten rating on Rotten Tomatoes. The main criticism wasn’t so much with the plot or the performances (even in negative reviews, most were praised) but some critics thought it was reckless in its depiction of teen sex and drug use. Keep in mind, there wasn’t anything like this at the time so it really came under attack for essentially not being responsible in regards to what it was showing the demographic that was the source of most of its success. In 2019, a lot of what Cruel Intentions shows doesn’t even get a blink, but viewing it now you definitely get a perspective that a lot of this wouldn’t fly had it been released today.
In a landscape unfortunately dominated by countless allegations of Hollywood sexual abuse and the #metoo movement, much of Cruel Intentions feels incredibly unsettling in 2019. Gay characters are verbally taunted and blackmailed, the pursuit of sex takes on a hunter-and-prey vibe, and to say that Cecille is taken advantage of by Sebastian is to put it lightly (look at the “you could be a model scene” today and tell me that the older Sebastian isn’t playing verbal mind games with the younger Cecille in order to get her to sleep with him). There aren’t a lot of redeeming qualities for some of the characters and since things are so taboo in regards to sex and power play between men and women today, I really doubt Cruel Intentions could make it to the multiplex without a ton of backlash behind it.
That being said, even in 1999, the film did explore the double standard of men who enjoy sex without much criticism versus women who do who are then labeled “sluts.” Sebastian is considered a legend for his sheer number of sexual conquests, yet Kathryn is demonized for hers: “God forbid I exude confidence and enjoy sex… I am the Marcia fucking Brady of the Upper East Side,” she laments. Is it enough to redeem her? Probably not, but to the audience, Kathryn is no longer just a heartless bitch who does what she wants just because she can.
Cruel Intentions actually tried to expand its universe on a few occasions. First, there was Manchester Prep which began as a potential series on FOX that had shot three episodes before being scrapped. This was then turned into the straight to video, Cruel Intentions 2 which functions as a prequel to the first film and starred a young Amy Adams as Kathryn. The film was again directed and written by Roger Kumble and has become a bit of a cult classic in its own right but mostly because it’s so bad that it’s good.
Cruel Intentions 3 followed in 2004 and has no real relation to the previous films other than the main character being the cousin of Kathryn. The film really isn’t remembered fondly by fans but I have personally seen it and think it’s a fun movie to make fun of if you have absolutely nothing else to do. Proving to be successful in its own right was Cruel Intentions: The Musical by Jordan Ross, Lindsey Rosin, and Roger Kumble. The run was originally scheduled for a ten-week engagement but the show was extended three times, through April 2018. The jukebox musical began as a pop-up engagement in Los Angeles before moving off-Broadway. The musical was well-received by critics, which features a mix of 90s tunes that revolve around the plot inspired by the film. Sarah Michelle Gellar, Reese Witherspoon, and Selma Blair even attended a showing too much fanfare on Instagram.
The last attempt to revive Cruel Intentions came in 2016 when Roger Kumble developed a pilot for a TV version that was shopped to NBC. Sarah Michelle Gellar reprised her role as Kathryn and it was set seventeen years after the events of the film and sees Bash Casey, son of Sebastian Valmont and Annette Hargrove, discovers his late father’s journal.
Upon discovering this, he is thrown into a world of lies, sex, and power with Kathryn Merteuil, Bash’s step-aunt, who attempts to gain control of Valmont International. The pilot, which was well-received by the network and tested high, was ultimately passed over because its soapy premise didn’t align with the other series on the network. Snippets of the pilot can be found below:
Cruel Intentions may not have aged well with its questionable attitudes towards manipulation through sex, but its juiciness, iconic moments and trailblazing mark it left on the teen film landscape makes it an essential watch to this day. In an era of squeaky clean teen movies, Cruel Intentions was a sexy cinematic firebomb, one dressed up in a blood-red bustier and dripping in quasi-incestuous dirty talk. A hotbed of elegant townhouses, preppy fashions, and lurid camp, Roger Kumble’s 90s classic feels both entirely of its time (even the film’s trailer is perfectly era-appropriate, a rapid-fire montage of film clips backed up by the likes of “Sneaker Pimps” and the theme song to Charmed). but it’s also oddly ageless. This sort of decadence never really gets old and like a fine wine, Cruel Intentions has aged gracefully 20 years later.
