Cruel Intentions

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.

Tropes associated with this work:
"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."
 * Adults Are Useless
 * 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.
 * Anti Villain:
 * Again, Kathryn (Type II). She's actually more of a Jerkass Woobie with the "woobie" part significantly reduced, in that so many of her cruel schemes are motivated by a Scrooge-like resentment toward the rest of the world.
 * Sebastian, too (also a Type II). He's as scuzzy as his stepsister in the beginning, but as the tale progresses his saving graces become much more evident.
 * 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.
 * 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
 * Betty and Veronica: Sebastian must choose between his affections for the sweet, blond Annette and the cruel, dark-haired Kathryn.
 * Bitch in Sheep's Clothing: Kathryn.
 * Bittersweet Ending or Downer Ending:
 * Blond Guys Are Evil: Sebastian and Blaine
 * Book Ends: The opening scene is the same as the last scene, except with
 * The Cake Is a Lie:.
 * Camp Gay: Blaine
 * Catholic School Girls Rule: Though their uniforms are more drab and conservative than is popularly portrayed.
 * Chekhov's Gun:
 * The Cobblers Children Have No Shoes: The psychiatrist's daughter is a psychological mess.
 * Not really, she's been seduced by someone who took nude pictures of her, and she just found out that they've been posted on the internet. Most women, not to mention young teenage girls, would be extremely upset at this, no matter how psychologically balanced they were.
 * Colour Coded for Your Convenience: Sebastian and Kathryn wear black and other dark colors, while Annette prefers white and pastels.
 * Corrupt the Cutie
 * Covered in Mud: In the second film, Sebastian pushes Kathryn in a pool of mud as a declaration of war.
 * Cry for The Devil:
 * But hey,
 * Disproportionate Retribution:
 * The Ditz: Cecile.
 * Divergent Character Evolution: The two main characters receive a negative version of this in the prequel.
 * Diving Save
 * Evil Gloating
 * Evil Tastes Good: Kathryn basically says this in one scene.
 * Evil Is Scared Of Feeling Good: "....She made me laugh."
 * 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
 * Flirty Stepsiblings
 * For the Evulz
 * For the Evulz

"Kathryn: It's all right for guys to fuck everyone... ...but when I do it, I get dumped for twits like Cecile. God forbid I exude confidence and enjoy sex. Do you think I relish acting like Mary Sunshine 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."
 * At least, she says that's the reason to Sebastian. It's heavily suggested that jealousy in regards to her twisted relationship with Sebastian was the actual driving force at work. In that light, "For the Evulz" is a less creepy reason.
 * French Jerks: Okay, technically Sebastian and Kathryn are French-Americans. But, they're still jerks.
 * Freudian Couch
 * Freudian Excuse: Kathryn states her's in one scene to Sebastian.


 * Hair of Gold: Annette
 * Hands On Approach: 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.
 * if you choose to be hopeful about her future.
 * Heroic Sacrifice:
 * 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.
 * Kissing Cousins / Twincest: The twins in the second movie claim to be Kissing Cousins, but were played by Real Life twins.
 * Large Ham: Ronald. "THE BLACK MAN IS GONE! THE BLACK MAN IS GONE!"
 * Some have accused Sarah Michelle Gellar of being this too.
 * Laser Guided Karma:
 * Though compared to her eighteenth-century counterpart, she gets off light, all things considered.
 * 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 Roman Catholic 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.
 * Love Makes You Evil: On the other hand,
 * The original ending was far less ambigious; in it,
 * Manipulative Bastard: Sebastian
 * Manipulative Bitch: Kathryn, IN SPADES
 * 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: Sebastian Valmont and Kathryn Merteul.
 * 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, teasing while in an interview for a college entrance and acceptance.
 * Pet the Dog: A small moment for Kathryn, when she tells Cecile's mother that Cecile's been seeing Ronald. Kathryn isn't just surprised, but shocked, maybe even angry and upset, when Cecile's mother is angry over Ronald being black (Kathryn thought she would be upset over Ronald being "hired help"). She may be manipulative and play games with people's lives, but race doesn't seem to be an issue for her (further emphasized when )
 * 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.)
 * Really Gets Around
 * Redemption Equals Death and Death Equals Redemption:
 * Secret Diary
 * Setting Update
 * Sinister Shades
 * 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.
 * Spit Trail Kiss
 * Straw Hypocrite: Kathryn uses gay slurs towards men ("Trevor's a fag", "Could you be more queer?") but has no problem kissing Cecile, twice, with tongue.
 * Teens Are Monsters
 * There Are No Adults: The few adults who do exist on rare occasions are clueless.
 * Token Minority: Ceciles' '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.
 * In case you ever forget Ronald's black, the subject of his race comes up in every other scene, such as his plans to write an opera based on Martin Luther King, and Kathryn riling him up to attack Sebastian by claiming Sebastian slept with Cecile.
 * Too Dumb to Live: Cecile.
 * Took a Level In Jerkass: Again, Cecile, who gets more bitchy and slutty as the film goes on, just as Kathryn had planned.
 * 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 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: Kathryn at the end.
 * 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 Protagonists
 * Virginity Flag: suddenly wears dark clothes in contrast to her former pastel wardrobe. Sebastian also wears a bright blue shirt to symbolize that he has.
 * Virginity Makes You Stupid: Subverted with Annette, played straight with Cecile.
 * Where Da White Women At: Ronald with Cecile.
 * 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.
 * It would be more accurate to say the trope is subverted or maybe deconstructed, since Kathryn (by her own admission) only pretends to be refined; in her private moments, she's quite the crass, foul-mouthed bitch. To a lesser extent, Sebastian, too, can be a bit of a lout.
 * Woman Scorned