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Film / Cruel Intentions

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"It amazes me someone as charming as you can be so manipulative."

Cruel Intentions is a 1999 American drama film written and directed by Roger Kumble, and starring Ryan Phillippe, Sarah Michelle Gellar and Reese Witherspoon. 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 was in the works for NBC, with Gellar returning to the role of Kathryn, but the network ultimately passed on the series.

In 2018, the film was adapted into a Jukebox Musical of 90s hits, which premiered Off-Broadway. The cast album is available for streaming on Spotify and YouTube.

Tropes associated with this work:

  • Adults Are Useless: The teenagers run the show and use their elders as pawns.
  • 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 Truth in Television. And let's not even get started on Kathryn's lingerie as daywear.
  • Armoured Closet Gay: Greg, a popular and wealthy football player at Sebastian and Kathryn's school, is in the closet and secretly hooking up with Sebastian's gay friend Blaine. Sebastian takes advantage of this, setting things up so that Blaine brings Greg to a hookup that Sebastian has access to and later photographing them in the act. Since Greg spends most of his time bragging to his teammates about his (female) hookups, Sebastian's threat to spread the evidence around school and show them to Greg's father is enough to terrify the boy into helping Sebastian with his scheme.
  • Boarding School: Technically, Manchester Prep is a day school, but it comes with the same tropes of spoiled students picking on Scholarship Students and engaging in Situational Sexuality — except for the one perfect and kind student, of course.
  • 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.
  • Casual Car Giveaway: Either this trope or Hero Stole My Bike is the only plausible explanation for that bizarre closing shot of Annette driving off into the desert behind the wheel of Sebastian's prized vintage Jag.
  • Casting Gag: Swoosie Kurtz appears in a modern day adaption of Les Liaison dangereuese after appearing in its seminal film adaptation a decade earlier.
  • Catholic School Girls Rule: Though their uniforms are more drab and conservative than is popularly portrayed.
  • Celebrity Cameo: A brief close-up of a family photo shows Sebastian and Kathryn with their parents alongside President Clinton and First Lady Hilary Clinton.
  • Cheating with the Milkman: Kathryn sarcastically remarks to Sebastian that her mother suspects that her stepfather is having an affair with the maid.
  • Chinese Laborer: Technically, Kathryn's handmaiden is Vietnamese.
  • 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 stony surroundings.
  • 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 colors, but shifts to wearing red as Kathryn and Sebastian begin to corrupt her.
    • In the scene where Sebastian seduces Cecile, he's wearing dark green ("go") while she's wearing bright red ("stop").
  • Consummate Liar: Kathryn, Sebastian. Annette's best friend, Greg, qualifies as well.
  • Cool Old Lady: In the original story Madame de Rosemonde becomes a trusted friend and wise mentor to Madame de Tourvel. In this version, Sebastian's Aunt Helen is just an eccentric biddy who whips up "iced tea" and pawns her charity duties off on her nephew and his girlfriend so she can go to the theater instead.
  • Deadpan Snarker: Sebastian and Kathryn both have mastered the art form.
  • Darker and Edgier: Of all the Les Liaisons Dangereuses adaptations, this modern version is definitely the edgiest and also arguably the darkest in the way that Kathryn Merteuil and Sebastian Valmont come across as even more brooding, nihilistic and emotionally disturbed than their 18th-century counterparts. Add the fact that all the characters are minors, and you've got an especially disturbing tale of sexual predation and death.
    • Also Darker and Edgier as far as teen flicks go. When Cruel Intentions came out in theaters, the film's ostensible target audience couldn't even get in to see it without a parent or guardian.
  • 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. Though to be fair, the heterosexual characters are also depraved, so it doesn't stand out as much.
  • The Dog Bites Back: Cecile is the one who photocopied the journals. And to further add salt to the wound, she personally hands one to Kathryn.
  • Establishing Character Moment: needing to overcome the challenge involved in casting a 26-year-old woman as an immature teenager, the film introduces Cecile dressed as small child would, in an animal-themed t-shirt and schoolgirl skirt (in contrast to the power suits worn by the more sophisticated villain protagonists). She fails to keep her legs closed while seated and fails to recognize Sebastian's reference to her wardrobe malfunction. Her mother has to close her legs for her, signalling her sexual vulnerability.
  • Ethnic Menial Labor: The film loves using this trope for comedic effect: The Caldwells have a Hispanic maid who says her one line, "¡Ay, caramba!" right on cue, while the Valmonts have two different Asian maids who give pedicures, an English butler, a creepy German chef, an Arab driver who wears a turban, and two Swedish masseuses. Of course, all their personalities are stereotypical and over-the-top.
  • Expy:
    • Cecile Caldwell is Cécile de Volanges.
    • Ronald Clifford is Chevalier Danceny.
    • Bunny Caldwell is Madame de Volanges.
    • Court Reynolds is Comte de Gercourt.
    • Helen Rosemond is Madame de Rosemonde.
    • Blaine Tuttle is Azolan.
    • Greg McConnell is Julie.
    • Mai-Lee is Victoire (sort of — she's just Kathryn's maid, not an accomplice in her schemes).
    • Gretchen and Mora are both Emilie (in a deleted scene).
    • Sebastian's journal represents the letters Vicomte de Valmont possessed.
  • Fan Disservice: Everything about the sexual relationship between Sebastian and Kathryn, once the audience realizes that they're actually step-siblings.
    • Sebastian getting Cecile drunk and then taking advantage of her state by coercing her into letting him perform oral sex on her. Albeit Played for Laughs.
  • Fanservice:
    • Selma Blair and Sarah Michelle Gellar making out for 47 seconds.
    • Kathryn lounging around in a pantsuit and lingerie that show off her Cleavage Window.
    • A shot of Sebastian's backside as he and Annette dress down to go swimming in the pool.
    • Annette stripping down to a blue swimsuit.
    • Sebastian and Annette's love scene.
  • The Fool: Realistically, Cecile seems to have more or less average intelligence for a 15-year-old girl, but she's treated as though she's mentally handicapped by her more sophisticated peers, which is continually Playedfor Laughs. More than anything, she's simply naive and lacks social graces. She gets better; at the end of the film, she finally understands the other characters' true motivations and helps to take down Kathryn.
  • French Jerk: Okay, technically Sebastian and Kathryn are French-Americans. But they're still jerks.
  • Freudian Slip: Mrs. Caldwell's racism slips out when her coffee arrives: "...Black! Brown sugar! No sugar!".
  • Golddigger: Sebastian sarcastically refers to Kathryn's mother as this, believing that she only married his father for his money.
  • Grande Dame: Tiffany Merteuil uses her status in the community to persuade Nouveau Riche social climbers to "throw money" at her self-serving charity, as Kathryn puts it.
  • 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.
  • High School AU: Of Dangerous Liaisons.
  • Hollywood Homely: In Cruel Intentions 3, Patrick's Freudian Excuse for being a sexual predator is that he isn't fortunate enough to be an Adonis, especially in comparison to one male character who's played by a former Abercrombie & Fitch model. He even says he feels like he has to "play up the homely" with nerdy clothes and unstyled hair to trick girls into thinking he's a Nice Guy.
  • Hookers and Blow: Sebastian and Kathryn make drugs and debauchery look so glamorous.
  • I Like My X Like I Like My Y: When Mrs. Caldwell's racism slips out, she tells the shocked waiter she was referring to how she prefers her coffee "—Black! Brown sugar! No sugar!".
  • Insult Friendly Fire: Sebastian drops a few "fag" and "fudge-packer" jokes after he catches Blaine and Greg together, then casually adds "no offense" with a look towards Blaine. Considering Blaine is pretty similar to Sebastian personallity-wise, and the entire thing was set up to manipulate Greg anyway, he doesn't seem to mind all that much.
  • I Want You to Meet an Old Friend of Mine: Sebastian hands Kathryn a magazine that has Jennifer Love Hewitt on the cover. Both Ryan Phillippe and Sarah Michelle Gellar had starred alongside her in I Know What You Did Last Summer.
  • The Jeeves: Naturally, the Valmont house has a proper English butler to manage a full staff of diverse Ethnic Menial Labor stereotypes.
  • Jukebox Musical: The stage adaptation has classic 90s songs, from "Genie in a Bottle" to "No Scrubs" to "Only Happy When It Rains."
  • Kick the Dog: Why did Sebastian humiliate his therapist and his therapist's daughter in the opening? Because "[the therapist] was charging him too much".
  • Large Ham:
    • Cecile's mother, played by Christine Baranski.
  • Light Feminine and Dark Feminine: Annette and Kathryn, respectively.
  • Love Is a Weakness: The movie's tagline is "In the game of seduction, there is only one rule: Never fall in love." Kathryn and Sebastian (at first) both live by this philosophy, which she uses as the basis for her "Reason You Suck" Speech against him.
  • 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."
      • More irony in that St. Cecilia is the patroness of music. Cecile, by her own admission, is a Dreadful Musician.
  • My God, What Have I Done?: After attacking Sebastian and inadvertingly causing his demise, Ronald, now remorseful after realizing he was manipulated, kneels in the street with Annette to tend to the dying Sebastian.
  • Nouveau Riche: The Caldwells in contrast to the Old Money Valmonts.
  • Noodle Incident: Cecile's mother about Sebastian: "I can't believe they didn't expel him after what he did to the school nurse."
  • Old Money: The Valmonts in contrast to the Nouveau Riche Caldwells.
  • Police Are Useless: The officer just seems dismayed that Sebastian rudely brushes him off after he repeatedly tries to point out that his car is in a no-parking zone.
  • The Precious, Precious Car: Sebastian's 1956 Jaguar XK 140 Roadster is his most prized possession. If he loses his bet with Kathryn, he has to hand it over to her. After Sebastian dies, Annette somehow ends up with the car. Although, production stills from the NBC spin-off TV series appear to show Kathryn eventually ends up with the car in San Francisco. Apparently, she hands it over to Sebastian and Annette's son, Bash Casey, once he comes out of the woodwork to claim his family name.
  • Prison Rape: If there's one decent thing about the Cruel Intentions 3 script, it's this witty line from Kathryn's cousin Cassidy, alluding to another character's earlier complaint that his promiscuous sex life has become boring: "You're off to prison, where the sex is never boring."
  • Racist Grandma: Cecile's mother, Mrs. Caldwell, seems like a cultured philanthropist but barely conceals her decidedly ignorant views, no doubt carried over from her generation. When she learns that Cecille is carrying on a dating relationship with Ronald, she promptly fires him and bans him from having any contact with her.
  • Rape Is a Special Kind of Evil: In Cruel Intentions 3, Patrick becomes the official villain of the movie when he crosses this line.
  • Reprise Medley: The Act One closer, "Only Happy When It Rains," concludes with all the main characters singing reprises of nearly every song in the act.
  • Scatterbrained Senior: Since Adults Are Useless anyway, it should come as no surprise that the residents at the nursing home that Sebastian and Annette visit are adorably senile.
  • Screw the Rules, I Have Connections!:
    • In Cruel Intentions 3, Cassidy's father founded an entire dorm hall just so she could have her own private suite, decked out in just about every standard college room code violation you can think of.
  • Secret Circle of Secrets: Kathryn's many extracurricular activities include running the Manchester Tribunal, a secret society of cruel popular kids at her snobby prep school. Basically, it's a rip-off of the Skull and Bones fraternity at Yale. Orders of business include such dastardly plans as ruining classmates' reputations, getting faculty members fired and scoring tickets to the Hole concert.
  • Setting Update: Of Dangerous Liaisons. It takes it from 18th century France to 1990s New York City, changing all the characters to teenagers.
  • Seven Deadly Sins: Both Sebastian and Kathryn have this:
    • Both are incredibly promiscuous people. (Lust).
    • Both mostly sit around and do little work. (Sloth)
    • Both come from a wealthy background. (Greed)
    • Kathryn is a drug addict and a bulimic. (Gluttony)
    • Kathryn envies her classmates. (Envy)
    • Kathryn and Sebastian despise others around them. Kathyrn in particular takes pleasure in manipulating others to cause as much damage or chaos to themselves and/or their peers as possible. (Wrath)
  • Sexual Karma: Sebastian and Annette's sex scene is depicted as tender and heartwarming in stark contrast to the other instances of sexual intercourse.
  • Shout-Out:
    • According to costume designer Denise Wingate, Selma Blair's red hoodie was supposed to invoke Little Red Riding Hood.
  • 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.
  • Social Climber: Bunny Caldwell hopes Kathryn will take Cecile under her wing so her popularity will rub off on her socially awkward daughter.
  • 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.
  • Sophisticated as Hell: Sebastian and Kathryn, being afforded the best education money can buy, mix phrases such as "au contraire" with adolescent potty-mouth language.
  • Stealth Pun: Cruel Intentions contains quite a few of these:
    • Just like the sterling cross in which Kathryn hides her drugs, she looks like a saint on the outside, but on the inside, she's filled with pure sin.
    • Sebastian sports a hunting jacket when he first meets his "prey", Annette.
    • Kathryn wears a snakeskin-print dress as she "slithers" seductively onto Sebastian's lap and hatches an evil plan.
    • Cecile wears a red hoodie when she sneaks out to go see Sebastian.
    • Sebastian has a bowl of maraschino cherries on his nightstand after he pops Cecile's cherry.
    • In the DVD commentary, the director points out that the way Sebastian suggestively points the neck of the champagne bottle toward his face when he says he and Kathryn should celebrate was intentional.
    • The way Sebastian strokes the handle of his tennis racket when he taunts Cecile isn't so stealthy.
  • There Are No Adults: The few adults who do exist on rare occasions are clueless or indifferent to what the kids are up to. Either way, they are not individuals to whom the children can appeal.
  • 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.
  • They Wasted a Perfectly Good Sandwich: When Kathryn is meeting with Cecile and her mother, the maid Mai-Lee sets a tray of tea or something in front of them, which no one touches. When Sebastian arrives, he sets the tray aside and it's completely forgotten by the time everyone has left the room.
  • Title Drop: Courtesy of Annette quoting a letter about Sebastian's manipulation: "Even more treacherous than he is attractive...he has never uttered a single word without some dishonorable intention."
  • 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")
  • Unsuspectingly Soused: Becomes something of a running gag across the series. Provides the page quote.
  • Verbal Backspace: 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.
  • Virginity Makes You Stupid: Subverted with Annette, played straight with Cecile. Not that Cecile is any smarter afterward.
  • Where da White Women At?: Ronald Clifford 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.
  • "You Do NOT Want To Know," Cecile says about being taken advantage of.

Tropes associated with the prequel, Cruel Intentions 2:

  • Adults Are Useless: In the second film, Kathryn and Sebastian's parents are essentially middle-aged versions of their respective children. Responsible authority figures apparently don't exist in this universe.
  • Alcoholic Parent: In the second film, Sebastian's mother is said to be "in rehab for the long haul," hence the reason why he moves in with his father.
  • 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.
  • Ambiguously Bi: Kathryn is going to date and fall in love with Court Reynolds at some point after the Prequel and before the first movie. However, she made out with Danielle when it was revealed they were accomplices to Sebastian.
  • Ambiguously Gay: Danielle pretends to fall in love with Sebastian, but in reality she couldn't care less about him. She's also not shown seemingly having any crushes on boys at her school, but she does make out with Kathryn when they are revealed to be accomplices. It's implied she was involved with Kathryn in a threesome with Sebastian after they join forces, however it’s not made clear if Danielle has any real affection for Sebastian.
  • Archnemesis Dad: Edward Valmont and his son Sebastian have a strained relationship even though they're exactly the same.
  • Betty and Veronica: This is reversed in the prequel where Kathryn is an icy blonde and Danielle is a warm brunette, and then subverted in the plot twist at the end when Danielle reveals that she's really just like Kathryn.
  • Bitch in Sheep's Clothing: Kathryn and Sebastian are obvious. It's revealed Danielle is just as bad as Kathryn.
  • Brother–Sister Incest: A pair of girls (who claim to be cousins, but are played by real-life twin sisters share a kiss in the shower while the male lead watches.
  • Butt-Monkey: Cherie in the second.
  • Chinese Labourer: In the prequel, Kathryn has another one who's a Cambodian refugee, but she's mistaken for Chinese and Japanese by her mistress.
  • Covered in Mud: In the second film, Sebastian pushes Kathryn in a pool of mud as a declaration of war.
  • Depraved Bisexual: Gretchen and Sarah, who seduce Sebastian and maintain an incestuous relationship with each other.
    • Kathryn may be this; see Ambiguously Bi above.
  • 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.
  • Downer Ending: The antagonists Kathryn, Sebastian and Danielle are all revealed to be cruel and manipulative by the end of the prequel, while the naive, spoiled yet good-natured Cherie has been seduced and recorded by Sebastian. It's heavily implied they are going to ruin Cherie’s reputation and get her expelled.
  • Evil Matriarch: Tiffany Merteuil shows her "love" for her family by being controlling and manipulative.
  • Freudian Excuse: In the prequel, a sobbing Kathryn uses the emotional abuse she endures from her mother as her excuse for being so mean.
  • Idle Rich: Sebastian and Kathryn each get a weekly five-figure allowance. And no, they don't mow the lawn for it. Meanwhile, middle-class Danielle has an after-school job at a used bookstore.
  • Kissing Cousins/Twincest: The twins Gretchen and Sarah claim to be cousins, but they look very identical to one another and they were played by Real Life twins.
  • Negative Continuity: In the first film Sebastian called Kathryn’s mother a "gold digging whore" which implies that Kathryn is the step-sibling who came from a poorer background. However, in the prequel Sebastian is the one from a poorer background. Many fans have noted this.
  • The Omniscient Council of Vagueness: In Cruel Intentions 2, the Manchester Tribunal convenes in the school's candle-lit attic with a a slide projector to discuss its plans to corrupt Sebastian and Cherie Claymon.
  • Pervert Dad: Although Sebastian's dad is certainly a sleazeball, in this case, it's actually Kathryn's mom who tries to get a little too close to her new stepson in the prequel.
  • Preacher's Kid: Before Headmaster Hargrove takes over the position, Danielle Sherman is the same thing, only she's not what she seems.
  • Prequel: Cruel Intentions 2... sort of. It was actually a pilot for a TV show that never happened.
  • Screw the Rules, I Have Connections!: Cruel Intentions 2 invokes this trope often to explain how the characters are able to pull off some pretty unbelievable scams (e.g., Sebastian switching his high school transcript with a forgery; Kathryn getting her hands on the real one).
  • 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.
  • Social Climber: In the prequel, Bunny Claymon has the exact same hopes for her daughter Cherie.
  • 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.
  • Twincest: Gretchen and Sarah. A scene shows the identical twins make out in the shower to entice Sebastian. Rather ridiculously, in the scene the girls claim to only be cousins.
  • Twin Threesome Fantasy: Gretchen and Sarah (played by Alicia & Annie Sorell) tease Sebastian with this in the shower, invoking Twincest as well (even though the two identical girls claim in dialogue to only be cousins).
  • Wicked Stepmother: Kathryn's mother tells Sebastian in no uncertain terms that if he doesn't keep an eye on his philandering father, the two of them will both be kicked "out on the street."


Video Example(s):

Alternative Title(s): Cruel Intentions 2


Colin Powell

How dare you accuse her of racism--she gave money to Colin Powell!

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