Kathryn Merteuil

Cruel Intentions

In the film, Kathryn is wealthy, beautiful and popular, She is part of the Upper East Side's social elite. Portrayed as a manipulative mastermind who uses and destroys people for her own amusement, she is also depicted as being addicted to cocaine, which she hides in her rosary, and may even suffer from Bulimia, as her ex-boyfriend Court states she's a "Bulimic Headcase" and Sebastian's private journal also states she's bulimic. She hides her true nature behind the facade of a deeply religious model student, fooling everyone she knows, except for her equally narcissistic step-brother Sebastian Valmont. Kathryn shows signs of sociopathic and narcissistic traits, treating the death of her supposedly "loved" brother with cold disdain, and gleefully enjoying destroying his life, as well as those of the people she perceives as threats or inferior to her. Despite this, she isn't an actual sociopath (she does not have antisocial personality disorder), as she still has had feelings for a few men in her life, and has displayed genuine emotions - traits sociopaths wouldn't exhibit. She has a strong superiority complex, but the extent of her interest in Sebastian is left ambiguous (she does cry when Sebastian's journal is made public, but whether this is because she finally saw how much Sebastian actually loathed/loved her, or if it is because people finally see her conniving, troubled mind, is left unanswered).

In the film, she's first seen discussing her prep school with Mrs. Caldwell and her daughter Cecile. Kathryn promises Mrs. Caldwell that she will look out for the sheltered and naive Cecile. However, she reveals to her step-brother Sebastian that her real intention is to use Cecile to take revenge on Court Reynolds, her ex-boyfriend, who had dumped her for Cecile. Kathryn asks Sebastian to seduce Cecile; yet he refuses as he is planning to seduce virgin Annette Hargrove, the daughter of their school's new headmaster. The two make a wager: Kathryn believes he cannot get Annette to bed, yet Sebastian believes he can. If Kathryn wins, she gets Sebastian's vintage Jaguar XK140; if Sebastian wins, Kathryn will have sex with him.

After numerous failed attempts of seducing Annette, Sebastian agrees to seduce Cecile. Cecile confesses to Kathryn that her music teacher, Ronald Clifford is in love with her. Afterwards Kathryn secretly tells Mrs. Caldwell about Ronald and Cecile's romance and Mrs. Caldwell intervenes in their relationship. Sebastian, in turn, calls Cecile to his house, ostensibly to give her a letter from Ronald. There, he blackmails Cecile and performs oral sex on her. The next day, Cecile confides in Kathryn, who advises her to learn from Sebastian so that she can make Ronald happy in bed.

After Sebastian sleeps with Annette, Kathryn offers herself to Sebastian as he has won the bet, but he refuses; he now only wants Annette. Kathryn begins showing signs of possessiveness towards Sebastian, and it is suggested that she is in truly in love with him. The next day, Kathryn taunts him and threatens to ruin Annette's reputation, so Sebastian pretends indifference to Annette and coldly breaks up with her. After Sebastian tells Kathryn that he has broken up with Annette and arranged for Cecile and Ronald to be together, Kathryn reveals that she has known all along that he was truly in love with Annette and manipulated him into giving her up. Kathryn knowing he came to make plans for them to have sex, rejects him. Once he leaves Kathryn calls Ronald to tell him that Sebastian slept with Cecile and (falsely) inform him that Sebastian hit her. This false information leads to Ronald attacking Sebastian and engineers his death. At Sebastian's funeral, Cecile distributes copies of Sebastian's private journal, made into a book by Annette, titled "Cruel Intentions". Kathryn is humiliated and rejected by her former friends, and her spotless reputation is ruined when the drugs hidden in her rosary are discovered.

Cruel Intentions 2

The straight-to-video sequel to the original film, a prequel, centers around a younger Kathryn. In the prequel film it is revealed Kathryn was born to Manhattan's Tiffany Merteuil a well-respected New York socialite. However, the prequel features several inconsistencies in its relation to the first film, such as the backstory concerning Kathryn's mother and Kathryn's overly outward meanspirited behavior, this is due to the film originally being written as a TV series retelling rather than a prequel. She attends Manchester Prep, a prestigious co-educational private school on just outside of the city. As in the first film, she manipulates and controls everyone around her, even seducing her school's headmaster, and then blackmailing him into letting her do whatever she wants. Soon her new Step-brother Sebastian Valmont and his father move in, and after their first meeting, Kathryn becomes quickly jealous of Sebastian as he out skills her in both piano and vocabulary.

The next day, at a school assembly, Kathryn, who is the student body president, delivers a speech to her classmates, but is interrupted by uncontrollable hiccups coming from a student, who then begins to choke on the gum that she was chewing in a bid to stop her hiccups. She is saved by the quick action of Another fellow student who performs the Heimlich maneuver, allowing the student to expel the gum, which ends up flying into Kathryn's hair. Afterwards Kathryn calls a meeting For the secret society of student elites, deciding upon the fate of the new students. This leads them to Cherie, the student with the hiccups, as well as the discovery that Cherie's family is wealthier than that of Kathryn; this, and the events of the assembly, cause Kathryn to seek a vendetta against Cherie.

The next night, Kathryn calls Cherie, asking if she'd like to attend a school event with her. Revealing to Sebastian that she plans to ruin Cherie's reputation. She takes Cherie to a popular nightclub, and tricks her into drinking several Long Island Ice Teas. After getting the attention of a male club goer, Kathryn tells Cherie he clearly likes her and that she has to "fuck him". Yet her plan fails once Cherie throws up on the young man's feet. After Sebastian angers Kathryn, whose day is interrupted by not being able to contact her driver, She conducts a plan to make him similar to her, and begins thinking on how she can mold Sebastian into a heartless womanizer. She starts by interfering with Sebastian's attempts to woo the fellow student Danielle. Kathryn first tries to tempt him away from Danielle by luring him with identical twins, who confide to Sebastian that Danielle is the only virgin at Manchester and she plans not to have sex with anyone unless she's truly in love.

Kathryn continues her attempt to sabotage Cherie, however it backfires, as Kathryn's mother tells her to become best friends with Cherie, in an attempt to encourage Cherie's mother to donate a large amount of money to the school. Sebastian soon professes his love for Danielle, only to find that she does not reciprocate. It turns out that Danielle is actually secretly working alongside Kathryn and is helping fulfill her secret plan to dupe Sebastian and make him heartless. Defeated by Kathryn's manipulation, a heartbroken Sebastian states he no longer has any attentions to ever fall in love again, afterwards he makes an alliance with Kathryn to dominate and manipulate others. She then tells Sebastian he should start with Cherie.

Cruel Intentions 3

While Kathryn herself does not appear in the third film in the franchise, the main character in this film - Kathryn's equally manipulative cousin Cassidy Merteuil - reveals that she is currently a patient in a methadone clinic.

Characterization

Kathleen Sweeney sees Merteuil as one of "Hollywood's Bad Girls", a stock character that Sweeney regards as appearing first in Veronica Sawyer in the 1988 film Heathers. Sweeney suggests that 1999 "gave viewers two manipulative dark-haired Queen Bees": Kathryn Merteuil in Cruel Intentions and Courtney Alice Shayne in Jawbreaker. Sweeney notes that in both films, "the Queens of Mean are punished by their peers, but not before laying out the game plan for wielding power in high school as visual "how-to" manuals for aspiring Queen Bees everywhere." Merteuil, Sweeney suggests, "maintains a Straight-A Uber Girl persona of innocence until the very end." Samantha Lindop classifies Merteuil as a fille fatale (a young femme fatale) and compares her to Adrian Forrester in The Crush.

Richard Burt suggests that Merteuil is "punished for being beautiful and smart" in that she "can't keep guys from dumping her for stupider girls." Burt goes on to note that Merteuil is a "bitch" who is "incapable of love" and "ultimately humiliated for her destructive nastiness."

Gellar's portrayal of Merteuil was parodied in the 2001 film Not Another Teen Movie, in which Mia Kirshner played Catherine Wyler, "The Cruelest Girl in School".