Cruel Intentions (1999)

Cruel Intentions (1999)
  • Time: 97 min
  • Genre: Drama | Romance
  • Director: Roger Kumble
  • Cast: Ryan Phillippe, Sarah Michelle Gellar, Reese Witherspoon


Slaking a thirst for dangerous games, Kathryn challenges her stepbrother, Sebastian, to deflower their headmaster’s daughter before the summer ends. If he succeeds, the prize is the chance to bed Kathryn. But if he loses, Kathryn will claim his most prized possession.


  • Get ready to enjoy your youth, to follow your sexual instincts and to manipulate everybody! I have to say that the title of the movie fits quite well with it, it is pure evil and malice. The main reason why this film caught my attention though was the extremely selfish, flawed characters. They were all enticing, and very difficult to like. The actors in this film were very well casted. Ryan Phillippe gives Sebastian the perfect transformation from cold-hearted casanova to a guy who genuinely starts to fall in love. But, it is Sarah Michelle Gellar who really shines in this film. I would recommend “Cruel Intentions” to many people, and it’s darker, sexier, more entertaining and less predictable than the average teenage film.

  • Ah, summer vacation! A time for most teenagers to kick back and relax. For horny stepsiblings Kathryn Merteuil (Sarah Michelle Gellar) and Sebastian Valmont (Ryan Phillippe), summer is an uninterrupted period for them to conspire and take pleasure in the fates of the victims they’ve ruined.

    “I’m sick of sleeping with these insipid Manhattan debutantes,” Sebastian complains at the onset of Cruel Intentions, originally titled Cruel Inventions and the latest adaptation of Choderlos de Laclos’ epistulary novel Les Liaisons Dangereuses. “Nothing shocks them anymore,” he sighs. Not to worry, says dear stepsister Kathryn, she has a mission for him. Her latest lover, Court Reynolds, has tossed her over for the virginal Cecile Caldwell (Selma Blair), a pretty but gawky deb that Kathryn has recently taken under her wing. Sebastian must deflower Cecile — thus will she be damaged goods to Court and thus Kathryn is avenged. Too easy, Sebastian snorts, he does have a reputation to uphold. Annette Hargrove (Reese Witherspoon), he tells Kathryn, is the real challenge.

    Annette is not only their new headmaster’s daughter, she is also the subject of a recent Seventeen magazine article (with Jennifer Love Hewitt, Gellar and Phillippe’s I Know What You Did Last Summer costar). In the article, Annette proclaims that she vows to remain pure until she finds true love and marries. She’s already found true love with her boyfriend, Trevor, who’s currently off backpacking in Europe. That circumstance leaves the door open for Sebastian and there is also the happy occurrence of his aunt Helen (Louise Fletcher) putting Annette up as a guest for the summer. Kathryn taunts that Annette is out of his league. So a bet is made. If Sebastian wins the bet by sleeping with Annette, then Kathryn, whom he’s been lusting after, will sleep with him. If he loses, then Kathryn will be the proud new owner of Sebastian’s 1956 Jaguar roadster. “I’m the only person you can’t have and it kills you,” she teases and promises him the orifice of his choice. . .if he wins. Sebastian agrees.

    “I wouldn’t expect a man of your experience to understand my beliefs,” Annette remarks at their first meeting. Clearly, she is no ordinary girl but he’s not about to let her morals get in his way. In fact, maybe her morals will be the way to break her down. “I look at you with your morals. . .I envy you,” he remarks, but she’s wary of everything he says. Meanwhile, Sebastian has agreed to help Kathryn with her plan to ruin Cecile. Cecile’s found a paramour in her cello teacher Ronald (Sean Patrick Thomas), Kathryn reveals, but “unfortunately our Don Juan is moving with the speed of a special Olympic runner.” As Kathryn writhes on top of Sebastian, she asks her aroused stepbrother how his other project is faring. He’s getting there, he gasps. “Until then,” Kathryn purrs, running her tongue over his cheek, “down, boy.”

    The first incarnation of de Laclos’s novel of sexual deceit and conquest was in its native tongue, Les Liaisons Dangereuses by Roger Vadim. Set in the late Fifties and saturated with a Thelonious Monk soundtrack, it starred the incomparable Jeanne Moreau and that marvelous Gerard Philippe (“How much do I love thee/Let me count the ways. . .”) as a swinging married couple whose open marriage proves to be their downfall. Stephen Frears’ award-winning 1988 adaptation, Dangerous Liaisons, is justifiably the most definitive with a coolly wicked Glenn Close and a sibilant John Malkovich as the scheming duo and Michelle Pfeiffer delivering an exquisite portrait of heartbreak as the virtuous Madame de Tourvel. Meg Tilly couldn’t quite match Pfeiffer’s anguish but Colin Firth and Annette Bening’s youthful protagonists held up against their predecessors in Milos Forman’s Valmont. This latest incarnation is the most youthful and its weakest but how can it not be when it’s got to follow in those footsteps? Still, this update proves that the material is indeed timeless and durable.

    Cruel Intentions is an enjoyable film in much the same way last year’s Wild Things was. (I personally didn’t take to that film’s self-conscious noir stance but I did admire its trashy spirit.) The settings are sleek, the costumes skimpy and the actors in fine form. Dawson’s Creek’s Joshua Jackson, always a delight, has a supporting role as a homosexual drug dealer. Blair, currently on Zoe, Duncan, Jack and Jane, is hilariously provocative as the boy-crazy Cecile. She flops around like a gosling, tripping over her legs and being literally tossed around by Sebastian and Kathryn. Phillippe as Sebastian has that narcissistic air the role requires and the cherubic facade that can both enchant and betray. Leonardo DiCaprio, I think, would have been a more proficient Valmont, especially in the character’s later stages where Sebastian finds himself genuinely falling for Annette. DiCaprio could have charted the erosion of Sebastian’s arrogance with more clarity. However, Phillippe does a creditable job. Gellar slinks through the role, vamping it up like a cat in heat. She is delicious and, of the crop of television youths balancing film and television gigs, is the most talented and deserving of a sturdy movie career.

    Witherspoon is lovely — she and offscreen beau Phillippe are the golden couple of the teenybopper set — but writer-director Roger Kumble makes his most grievous mistake in her character. Part of the pull in the triangle is the virtue of her character. In the novel and in previous adaptations, the character was not only faithful to her husband but loyal to her faith as well. Valmont’s seduction results in the rupture of both faiths. She is aware of what she is doing, her desire suffocates her and Valmont, already in love with her purity, is pained by what he has caused. Annette, on the other hand, never fully convinces us of her devotion to either her boyfriend or to God. During the pivotal scene where Sebastian breaks with her, Annette is too strong for the drama to resonate. It’s not that she must be weak, but she must be broken and perhaps Witherspoon is too modern an actress to express that pathos. Or perhaps too limited in experience and scope to understand her dilemma.

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