Film / Cruel Intentions

How can someone so charming be so manipulative?

Cruel Intentions is a 1999 American drama film written and directed by Roger Kumble. The movie is a comedic and dramatic appropriation of the 18th-century French epistolary novel Les Liaisons Dangereuses by Laclos, but unlike other modern film versions of the novel (Dangerous Liaisons) is not set in the France of that time.

The story follows a handful of wealthy teenagers living in modern New York City. The plot is mainly driven by a bet held between the two main characters, and it heavily involves manipulation, seduction, and love in a rich and sophisticated socially elite youth atmosphere.

The film started as an independent film with a much smaller budget, and was later picked up by Columbia Pictures. The film was released on March 5, 1999. It was later followed by two direct-to-video films: a prequel, Cruel Intentions 2, and a sequel, Cruel Intentions 3. A pilot for a sequel television series set 15 years later is currently being filmed, with Gellar returning to the role of Kathryn.

Tropes associated with this work:

  • Adaptational Heroism: Sebastian is presented far more sympathetically than his counterpart in the original novel and its adaptations.
  • Adults Are Useless: The teenagers run the show and use their elders as pawns. In the second film, Kathryn and Sebastian's parents are essentially middle-aged versions of their children respectively. Responsible authority figures apparently don't exist in this universe.
  • Age-Inappropriate Dress: Despite only being in high school, Sebastian and Kathryn wear power suits as loungewear. Although, for the Upper East Side in New York City, this is more or less Truthin Television. And let's not even get started on Kathryn's lingerie as daywear.
  • Age Lift: Kathryn and Sebastian's counterparts in the novel were in their 40s but are now around seventeen.
  • All Girls Like Ponies: The second movie uses a racy version of this trope where proper horse-riding technique is used as a metaphor for sex.
  • All Girls Want Bad Boys: Sebastian's main charm seems to be that he is "bad boy," which ultimately works on Annette.
  • Alpha Bitch: Deconstructed with Kathryn. She is the most popular girl in school and regularly abuses the privilege, but she is also a borderline recluse much of the time and confesses to Sebastian that she isn't really happy with her life. Honestly, her desire to want to humiliate other girls is more out of envy than pure sadism.
  • Am I Just a Toy to You?: Inverted. Sebastian tells Annette that she was this when he breaks up with her. She doesn't believe him, because he is visibly trembling and miserable as he says it, but still finds it too painful to stay with him.
  • And Now For Something Completely Different: Watching it today, it's clear that Cruel Intentions is far and away from the typical cheesy teen-pop fare that was common in Hollywood in the late 1990s and early 2000s, though ironically it preceded most of the films it's being compared to here.
  • Armoured Closet Gay: Annette's friend Greg plays on the football team and makes himself out to be a heterosexual jock type. Of course he isn't, which is taken advantage of by Sebastian.
  • As You Know: For some reason (i.e., exposition), Kathryn has to remind her stepbrother not only who her ex-boyfriend is, but also that he just dumped her, like, last weekend.
    • Also, this awkward exchange:
    Sebastian: Nice to see you agan, Mrs. Caldwell!
    Mrs. Caldwell: You remember my daughter, Cecile.
  • Batman Cold Open: Sebastian's session with the psychologist to deal with his "sexual addiction." This also serves as his Establishing Character Moment, where he comes onto his doctor who, after he leaves, receives a phone call from her crying daughter telling her that Sebastian seduced her and let him take nude photos of her that he posts on the internet. Game, set, match.
  • The Bet: The whole plot revolves around a bet two step siblings make. Kathryn promises she will sleep with Sebastian only if he manages to sleep with Annette (the headmaster's daughter) before school begins. Sebastian ends up falling in love with Annette instead.
  • Betty and Veronica: Sebastian must choose between his affections for the sweet, blonde Annette and the cruel, dark-haired Kathryn.
  • Bittersweet Ending: Kathryn gets her comeuppance in the end, but Sebastian dies, both Annette and Cecile seem to have become more corrupted from the experience, and even Kathryn's defeat (set to The Verve's "Bittersweet Symphony") isn't pleasant. It's more bittersweet if you choose to be hopeful about all three girls' futures, so it's all up to the audience to decide in the end.
  • Black Comedy Rape Sebastian essentially date rapes Cecile by first getting her Unsuspectingly Soused and then using coercion to make her relent to him performing sex acts on her. And it's Playedfor Laughs the whole time.
    • Hell, if Sebastian's Wangsting and the tragic climax and dénouement were edited out, the whole film could pass for a Black Comedy. The opening scene alone is a comedic masterpiece.
  • Book Ends: The opening scene is the same as the last scene, except with Annette replacing Sebastian. In the original ending, this made much more sense given the state of Annette's character alignment.
  • Brainy Brunette: The calculating, devious Kathryn.
  • Brother-Sister Team: The manipulative Kathryn Merteuil and Sebastian Valmont are step-siblings - and yes, that particular loophole is milked for all it's worth.
  • The Cake Is a Lie: When Sebastian comes to collect from Kathryn, she just laughs in his face and gives him a "Reason You Suck" Speech. Unusually for this trope, there is no indication that it was a lie from the start, and it seems like Kathryn intended to keep her end of the deal until she realised Sebastian had truly fallen for Annette and got jealous.
  • Camera Fiend: Sebastian seducers the psychiatrists daughter by taking pictures of her legs- later, he's seen photographing a blithely ignorant Cecile.
  • Camp Gay: You can tell Blaine is a Depraved Homosexual because his dye job matches his sweater vest — it doesn't get much campier than that. Also, he displays mannerisms that are stereotypically associated with gay men.
  • Can't Hold His Liquor: Cecile gets pretty tipsy off one Long Island Iced Tea.
  • Catholic School Girls Rule: Though their uniforms are more drab and conservative than is popularly portrayed.
  • Chekhov's Gun: Sebastian's journal. He's seen with it throughout the film writing or inserting pictures. He later delivers it to Annette for her to read in order to wipe his slate clean. After Sebastian's untimely death due to Kathryn's manipulation, Annette does something else with it. See Cry For The Devil below.
  • The Cobbler's Children Have No Shoes: The psychiatrist is about to go on a book tour to promote her Great Parenting manual, however when she finds out her daughter was manipulated and had nude photos of herself put on the internet, her response is neither kind nor particularly constructive.
  • Cold Ham: One of the pleasures of watching this film has to be watching and listening to Gellar take frequent bites out of the tony surroundings - dainty bites, to be sure, but all the more memorable precisely because of that. And most of them in the same cynical California cheerleader voice she made famous.
  • Color-Coded for Your Convenience: Sebastian and Kathryn wear black and other dark colors, while Annette prefers white and pastels. Cecile initially wears white and other light colours, but shifts to wearing red as Kathryn and Sebastian begin to corrupt her.
  • Consummate Liar: Kathryn, Sebastian. Annette's best friend, Greg, qualifies as well.
  • Cool Car: Sebastian's Jaguar, which Kathryn has her eye on. In the end, Annette drives it off into the sunset after exposing Kathryn Sebastian's funeral.
  • Covered in Mud: In the second film, Sebastian pushes Kathryn in a pool of mud as a declaration of war.
  • Defiant Captive: Cecile comes off as surprisingly tough when Sebastian is performing cunnilingus on her against her will. She merely glares and acts annoyed, only breaking down after Sebastian leaves.
  • Depraved Bisexual: Kathryn doesn't necessarily identify as bisexual per se, but that doesn't stop her from convincing Cecile that it would be a good educational experience to "practice" the art of making out on each other to test her inhibitions.
  • Depraved Homosexual: Blaine, who's openly gay, is eager to help Sebastian blackmail closeted Greg by getting him into bed so that Sebastian can walk in on the two men together and take photos of them in a compromising position. To be fair, the heterosexual characters are also depraved, so subverted.
  • Divergent Character Evolution: An inverted example. In the prequel Sebastian is kind and considerate, and Kathryn is cold, calculating, and uses sex as a weapon; and frequently destroys other peoples lives for her own amusement or revenge. Both try to convert the other to their way of thinking, but Sebastian is broken by Kathryn and ends up becoming a male version of Kathryn.
  • Diving Save: Sebastian does this to save Annette from an oncoming taxi.
  • The Dog Bites Back: Cecile is the one that photocopied the journals. And to further add salt to the wound, she personally hands one to Kathryn.
  • Evil Gloating: Kathryn sure loves doing this. Half her lines consist of it.
  • Evil Tastes Good: Kathryn basically says this in one scene.
  • Expy:
    • Sebastian Valmont is Vicomte de Valmont
    • Kathryn Merteuil is Marquise de Merteuil
    • Annette Hargrove is Madame de Tourvel
    • Cecile Caldwell is Cécile de Volanges
    • Ronald Clifford is Chevalier Danceny
    • Bunny Caldwell is Madame de Volanges
    • Court Reynolds is Comte de Gercourt
    • Helen Rosemont is Madame de Rosemonde
    • Sebastian's journal represents the letters Vicomte de Valmont possessed
  • Fille Fatale: Kathryn is the poster child of this trope. While she's a brilliant Chess Master, her body is her weapon of choice for manipulating boys — and sometimes even girls.
  • Flirty Stepsiblings: Sebastian and Kathryn really push the envelope as far as they can with this trope. There's nothing subtle about the stepbrother and stepsister's sexual attraction to each other — viewers are clearly supposed to be shocked and disgusted, if not salaciously turned on.
  • For the Evulz
    Kathryn: You were very much in love with her. And you're still in love with her. But it amused me to make you ashamed of it. You gave up on the first person you ever loved because I threatened your reputation. Don't you get it? You're just a toy, Sebastian. A little toy I like to play with. And now you've completely blown it with her. I think it's the saddest thing I've ever heard.
  • French Jerks: Okay, technically Sebastian and Kathryn are French-Americans. But, they're still jerks.
  • Freudian Couch: Sebastian lies on the couch in his therapist's office.
  • Freudian Excuse: Kathryn states hers in one scene to Sebastian.
    Kathryn: Eat me, Sebastian. It's okay for guys like you and Court to fuck everyone... ...but when I do it, I get dumped for innocent little twits like Cecile. God forbid I exude confidence and enjoy sex. Do you think I relish acting like Mary Sunshine twenty-four seven so I can be considered a lady? I'm the Marcia-fucking-Brady of the Upper East Side... ...and sometimes I want to kill myself. There's your psychoanalysis, Dr. Freud. Now tell me, are you in, or are you out?
  • Getting Crap Past the Radar: Sebastian isn't interested in his stepsister's offer of sex if he wins until Kathryn adds, "You can put it anywhere..."
  • Good Smoking, Evil Smoking: Sebastian is an "evil smoker".
  • Hair of Gold, Heart of Gold: Beautiful young virgin Annette.
  • Hands-On Approach: Cecile and her music teacher Ronald, with a Cello.
  • Heel–Face Turn: Sebastian, who's every bit as slimy as his stepsister at the beginning, just couldn't continue being such a jerk after Annette genuinely won his heart. According to information on the television series, Kathryn by all appearances seems to have made one too following the film, even running a rehab movement for troubled youths like she used to be. However...
  • Heroic Sacrifice: After Annette is pushed onto the road by Ronald during his and Sebastian's fight, Sebastian pushes her out of the way of an oncoming car and gets hit himself. He would succumb to the accident.
  • I'm Back: Sebastian tries to invoke this after breaking up with Annette, but he overdoes his performance and he's clearly been crying, so it's not all that convincing.
  • Instant Seduction: Sebastian, apparently. In his first scene he tells a girl that she's beautiful, and the next we see him a few hours later he's already had sex with her.
  • Invisible Parents: Sebastian and Kathryn's parents are only vaguely mentioned as being out of the country.
  • Ironic Echo: Annette meets Kathryn at the end, just before it emerges she's released the journal, thus destroying the latter's reputation and turns her "in times of trouble, I turn to Jesus" line on her. Kathryn doesn't realise a thing.
  • Kick the Son of a Bitch: The deleted scene in which Sebastian slaps Kathryn. Good God, did she deserve it. Unfortunately, the scene had to be deleted because Sebastian then went too far after the slap, almost forcing himself on Kathryn sexually.
  • Kid-anova: At 17, Sebastian is already "sick of sleeping with these insipid Manhattan debutantes."
  • Kissing Cousins / Twincest: The twins in the second movie claim to be Kissing Cousins, but were played by Real Life twins.
  • Lame Rhyme Dodge: Said by Sebastian to an elderly woman who's hard of hearing.
    Sebastian: Then I fucked your daughter.
    Woman: What?!?!?
    Sebastian: I said, would you like some water?
  • Large Ham:
    • Cecile's mother, played by Christine Baranski.
  • Laser-Guided Karma: Kathryn's downfall comes about from people whom she screwed over. Her secrets are exposed by the journal of Sebastian, which was copied by Annette and distributed to the student body by Cecile.
  • Lean and Mean: In the form of the rail-like Kathryn.
  • Light Is Not Good: Kathryn can't seem to stop telling people how fortunate she is to be a part of the Christian faith. She speaks as if Jesus Christ is her greatest ally and even wears a rosary as a necklace in public. But despite all that she is an insufferable elitist, and manipulative, spiteful and cruel, and stashes cocaine inside a hollowed-out crucifix at the end of her rosary.
  • Love Redeems: Sebastian, sort of. He comes clean about everything and sacrifices his life for Anette.
  • Love Makes You Evil: The last shot of the movie, (Annette driving Sebastian's car, wearing Sebastian's sunglasses, and smirking like Sebastian did at the start of the movie) indicates that loving Sebastian may not have been all too good for Annette... The original ending was far less ambiguous; in it, Annette DOES become evil and, instead of publishing Sebastian's journal and expose Kathryn, uses the possibility of doing that to blackmail Kathryn into becoming her minion, who she plans on using to completely fuck around with the social order of her father's school.
  • Madonna–Whore Complex: Kathryn speaks against this, talking about the Double Standard of boys being able to sleep around while she must pretend to be a Madonna in order to avoid being classed as a Whore. Her whole game plan is to corrupt Madonnas Annette and Cecile and turn them into Whores.
  • Manipulative Bastard: Sebastian and Kathryn both excel at manipulating people to their own advantage.
  • Meaningful Name:
    • Sebastian's surname, Valmont, consists of the French words val (literally meaning "vale", the old-fashioned word for "valley") and mont ("mountain"). Sebastian starts out the movie "high" (cool and arrogant) but by the climax has been brought low and made pathetic.
    • Cecile:
      • Kathryn and Sebastian succeed in making Cecile impure - which is ironic, because her name is the French form of "Cecilia" - the Catholic saint who is famously known as "The Incorruptible."note 
      • More irony in that St. Cecilia is the patroness of music. Cecile, by her own admission, is a Dreadful Musician.
  • Noodle Incident: Cecile's mother about Sebastian: "I can't believe they didn't expel him after what he did to the school nurse."
  • Not Blood Siblings: Right before Kathryn propositions her stepbrother for anal sex, she makes it a point to clarify for the audience that her mother only married Sebastian's father fairly recently.
  • One Degree of Separation: Sebastian and Blaine automatically draw the conclusion that Annette and Greg must know each other because they both happen to be from Kansas, a relatively large state — and lo and behold, they're right. In fact, they grew up together.
  • Panty Shot: Cecile Caldwell (Selma Blair) sitting on the couch with her legs open, giving a view of white panties under her khaki short skirt.
  • Pet the Dog: Sebastian deliberately goes for this when volunteering to help Annette work at the old people home, with humorous results.
  • Popular Is Dumb: Subverted as Kathryn and Sebastian are in fact pretty intelligent.
  • Practice Kiss: In a Les Yay example of this trope, this is proposed by Manipulative Bitch Kathryn to the innocent Cecile, who is worried about making a fool of herself when kissing her boyfriend for the first time. After the kiss Cecile is left breathless, and unconsciously leans forward for more as Kathryn pulls away.
  • Prequel: Cruel Intentions 2....sort of (It was actually a pilot for a TV show that never happened.) Ironically, Roger Kumble himself is now aiming to create a sequel TV show.
  • Really Gets Around: Sebastian. Kathryn notes the hypocrisy that nobody thinks any less of him for sleeping with everyone, but she has to keep her sexual liaisons a secret.
  • "Reason You Suck" Speech: Kathryn gives one to Sebastian after she tricks him into dumping Annette.
    Kathryn: You were in love with her. And you’re still in love with her. But it amused me to make you ashamed of it. You gave up the first person you ever loved, because I threatened your reputation. Don’t you get it? You’re just a toy, Sebastian. A little toy I like to play with. And now you’ve completely blown it with her. I think it’s the saddest thing I’ve ever heard.… So I assume you’ve come to make arrangements. But unfortunately, I don’t fuck losers.
  • Redemption Equals Death: Sebastian dies saving the girl he loves from a car crash and in death he owes up to his and his sisters' crimes through his journal that Annette gets published, which exposes their cruel intentions.
  • Revenge by Proxy: The whole reason Kathryn sets Sebastian onto Cecile is to get to Cecile's current boyfriend, who is Kathryn's ex.
  • Rich Boredom: Supposedly, Kathryn somehow manages to balance a hard drug addiction and alcoholism and an exemplary academic resume (by blackmailing all her teachers perhaps?). Yet as far as we can tell, she and Sebastian seem to have nothing better to do than lounge around their palatial townhouse (or country estate if they feel like a change of scenery) while placing bets on how many people they can sleep with and lives they can ruin just to pass the time.
  • Secret Diary: Sebastian has one, as a carry-over from the original novel (which was made up of letters the characters wrote to each other). It's what exposes Kathryn at the end.
  • Setting Update: Of Dangerous Liaisons. It takes it from 18th century France to 1990s New York City, changing all the characters to teenagers.
  • Shower Scene: Cruel Intentions 2 has a shower scene with a pair of twins making out in front of Sebastian, which, incidentally, is the only thing people remember about the film.
  • Sinister Shades: After Ronald is fired by Mrs Caldwell, he is met outside the elevator by Sebastian and Kathryn, who are both wearing sunglasses and smirking, with the intentions of using Ronald's affiliation with Cecile to further their bet. Also, Sebastian is seen wearing the same shades in his first introductory scene, driving to his therapy session with Dr Greenbaum, where it is revealed he had been seducing Greenbaum's daughter to humiliate her. At the end, Annette's final scene (after outing Kathryn) is her driving out of New York City in Sebastian's car, his journal beside her, and smirking somewhat deviously...while wearing Sebastian's sunglasses.
  • Sissy Villain: Sebastian, who is symbolically emasculated not only by Kathrynnote , but also in a way by Cecilenote .
  • Smug Snake: Kathryn spirals into this toward the end. For much of the movie, she's very competant and successful at manipulation, but she really overreaches when she turns on Sebastian, whose assistance was a big contributor to her past success.
  • Some of My Best Friends Are X: Cecile’s mom denies disapproving of Ronald dating Cecile because he’s black, citing the fact that she’s donated money to Colin Powell’s foundation. Ronald is duly impressed.
  • Spared by the Adaptation: The ending of the stage musical parody ambiguously suggests that Sebastian faked his death to expose Kathryn.
  • Spit-Trail Kiss: The infamous lesbian kiss between Kathryn and Cecile was like this.
  • Stepford Smiler: Katherine pretends to be an upstanding Junior League-type schoolgirl, when in reality she's an oversexed, scheming coke fiend who takes out her frustrations on her fellow female classmates by persuading them to sleep around and ruin their reputations as a result.
  • Tears of Remorse: Kathryn at the end of the film, once she is exposed as the manipulative bitch she is and, upon reading about herself in Sebastian's published journal, she finally seems to grasp how messed up a person she is. Also, Sebastian wrote of her as being "my true love" despite all her faults, making her feel guilty about her indirect role in his death.
  • The Ghost: Allegedly, Annette is already in a committed relationship with a loving boyfriend known as "Trevor," who's conveniently absent for the entire movie as Sebastian moves in on her. Also, Court is supposed to be Cecile's official boyfriend, yet he only makes one appearance in a flashback, and the two are never seen together.
  • The Tease: Kathryn, at one point grinding on Sebastian to convince him to sleep with Cecile.
  • Teens Are Monsters: Especially in the prequel, and even more especially in the unaired episodes of the canceled television series that became the prequel. Almost every student at Manchester Prep turns out to be every bit as cruel as Kathryn and Sebastian.
  • There Are No Adults: The few adults who do exist on rare occasions are clueless.
  • The Three Faces of Eve: The three girls: Annette (wise and mature) as the wife, Kathryn (cold, manipulative Femme Fatale) as the seductress and Cecile (sheltered Naïve Everygirl) as the child.
  • Token Minority: Cecile's 'unsuitable' lover, Ronald. Kathryn was expecting Cecile's mother to be shocked at the idea of her daughter dating the "hired help". She's surprised when the mother is instead horrified because Ronald's black.
  • Took a Level in Jerkass: Again, Cecile, who gets more bitchy and slutty as the film goes on, just as Kathryn had planned.
  • Totally Radical: Cecile's dialogue, particularly when she says goodbye to Ronald with "Peace out!" much to Kathyrn's disgust.
  • Tsundere: Sebastian pretty much accuses Annette of being this at one point ("Hot one minute, cold the next")
  • Unholy Matrimony: Sebastian and Kathryn's parents. When she tells him that her mother suspects his "drunk, impotent" father of doing the maid he says excellent, while he calls her mother a "gold digging whore".
  • Unsuspectingly Soused: Becomes something of a running gag across the series.
  • Villainous Breakdown:
    • Sebastian originally had one when Kathryn refuses to sleep with him even after he dumps Annette, going into a tearful, psychotic tirade and even hitting Kathryn. However, it was cut out because it lessened the feeling that Sebastian could truly be redeemed. Interestingly, Kathryn still tells Ronald that Sebastian hit her, making it seem like a lie when it was originally meant to be true.
  • Villain with Good Publicity: Kathryn is obsessed with maintaining her wholesome reputation as the student body president who attributes all her success to her unwavering piety, and she'll go to any length to destroy anyone who threatens the image that she's worked so hard to create.
  • Virginity Flag: Annette suddenly wears dark clothes with a more revealing neckline in contrast to her former high-necked pastel wardrobe. Sebastian also wears a bright blue shirt to symbolize that he has fallen in love with her.
  • Virginity Makes You Stupid: Subverted with Annette, played straight with Cecile. Not that Cecile is any smarter afterward.
  • Where Da White Women At?: Ronald is instantly smitten with Cecile as well as, as it turns out, Kathryn despite that neither really seems like his type personality-wise. Suffice it to say, Cecile's mother does not approve of her daughter liking her men like she likes her coffee.
    • In a deleted scene, Kathryn uses the scandalous nature of her relationship with Ronald to her advantage by manipulating him into believing that Sebastian is a violent racist.
  • Wicked Cultured: Kathryn speaks Vietnamese, French and has sashimi as a midday snack. Sebastian rides, is an expert marksman and quite well read. He also drives a vintage Jaguar, which Kathryn covets.
  • Woman Scorned: The story of Kathryn's life. Halfway through the film, she delivers a Motive Rant about how she's sick of being dumped by guys like Court, Sebastian and Ronald for "innocent little twits" like Cecile and Annette. (Annette isn't really a twit, but Kathryn would consider her one just for being a Nice Guy.)
  • Verbal Backpedaling: Mrs. Caldwell does this after a politically incorrect outburst.
    Kathryn: She's so young, and he's so —
    Mrs. Caldwell: Black! Brown sugar. No sugar.
  • "You Do NOT Want To Know," Cecile says about being taken advantage of.
  • Your Cheating Heart: This is essentially the entire plot of the story. Annette cheats on Trevor both physically and emotionally with Sebastian. Sebastian arguably cheats on Kathryn emotionally with Annette. He also cheats on Annette physically with Cecile. Cecile cheats on Court both physically and emotionally with Ronald. She also cheats on both of them physically with Sebastian. Ronald cheats on Cecile physically with Kathryn. Kathryn hooks up with Ronald to make Sebastian jealous. It's implied that Court cheated on Kathryn with Cecile at least emotionally. And everybody lives — or dies — unhappily ever after.