Note: For anyone who read my essay, "The Cruel Intentions of Teenage Audiences," this review is based on my second viewing, with an audience, thankfully, that acted much more mature.

What an ingenious concept: Take a famed 18th-century novel, in this case Choderlos de Laclos's Les Liaisons Dangereuses, which has subsequently been adapted to film three times (in 1959, 1988, and 1989, respectively), and update it to modern-day New York City with wealthy teenage characters. Walking such a fine line with the classic source material could have easily turned out disasterously, or even laughably, but screenwriter Roger Kumble (also making his auspicious directing debut) has wisely stuck surprisingly closely to the book, as well as the 1988 film version by Stephen Frears, "Dangerous Liasons," and has unexpectedly captured the tricky tone, as well, between absolute wickedness and ultimate redemption.

Sebastian Valmont (Ryan Phillippe) and Kathryn Merteuil (Sarah Michelle Gellar) are two devious step-sibling Manhattan socialites on their summer break before their senior year in an exclusive private school, who amuse themselves by playfully flirting with each other and bragging about their various sexual conquests. They are quickly growing bored, however, by the growing air of predictability in the games they play with potential love interests whom they care nothing for. When Kathryn is dumped by one of her boyfriends for the clumsy, childish 15-year-old virgin Cecile Caldwell (Selma Blair, star of "Zoe, Duncan, Jack and Jane"), she is outraged, and asks Sebastian for a favor: seduce Cecile and then spread rumors about her promiscuity, even though she has her eyes set on her black music teacher, Ronald (Sean Patrick Thomas). The stakes grow even higher between Sebastian and Kathryn when she makes a wager with him concerning if he can seduce Annette Hargrove (Reese Witherspoon), a young woman whose father is going to be the new headmaster of their school, and whom has recently written an article in "Seventeen" magazine where she professes her plans to wait until marriage to lose her virginity, before school starts. If he loses, she gets his vintage Porsche. And if he wins, he can enjoy Kathryn in any way he wants. "I'm the one person you can't have," Kathryn tells Sebastian, "and it kills you." Sebastian accepts, but while spend time with Annette, the unthinkable happens: he actually begins to form real, human feelings for her, despite initially only using her.

"Cruel Intentions" is a sleek and stylish comedy-drama that makes no compromises with its title: the two main characters in the film, and even some of the supporting ones, are extremely cruel and emotionally sick people who get their kicks out of using people. Because of this, the film is also certainly not your normal so-called "teenager" movie, and I could easily imagine adults also getting involved in the characters' plight, just like many have with "Dangerous Liasons."

Even if the characters aren't all likable, they are written with a richness you don't often see, and the dialogue between Sebastian and Kathryn is truly fetching and enjoyable, as they don't always say what they mean, or slyly use double entendres to stand for what they are saying. And as played by Phillippe and especially Gellar, the two actor are certainly up to the challenge. Gellar finally has proven with this film that she can very well be a wildly versatile actress that can play sweet with one role and be deceptive and hateful with the next, as she does here. Even if Phillippe isn't always up to her level, he is still well-cast in the role and plays several scenes with a brutal honesty (even if, in the film, he is supposed to be deceiving someone).

As the innocent, beautiful Annette, Witherspoon turns in yet another fine performance to add to her impressive resume (which includes outstanding turns in such films as 1991's "The Man in the Moon," 1996's "Freeway," and 1996's "Fear"), and in one vital dramatic sequence, she is able to transform a potentially cliched scene into something that is thoroughly poignant. Witherspoon also works very well with Phillippe, even if there aren't quite enough scenes between them to believe that they have fallen in love, and they make a quite charismatic pair (perhaps because they are a couple in real life, just recently engaged).

In the fourth and final central role is Blair (in her first starring film), who is a standout as the juvenile Cecile. That Blair is 26-years-old (about two to five years older than the other cast members, even though she plays someone two or three years younger) and is able to believably play a high school freshman only goes to show that she is also very talented, as well as has a firm comic sensibility, since many of her scenes rely on humor. All other actors in the film have relatively small roles who are used as pawns in Sebastian and Kathryn's scheme, including Thomas, as the music teacher; Eric Mabius, as a teenage football player and closeted homosexual; Joshua Jackson, as Sebastian's gay friend; and Christine Baranski as Cecile's aristocratic mother.

Although the story at hand is ultimately a tragic one, and includes a masterfully-done conclusion involving Gellar that rivals the one in "Dangerous Liasons" with Glenn Close, "Cruel Intentions" is also an often very funny comedy, particularly when dealing with small blink-and-you'll-miss details involving the characters, the always-amusing dialogue, and the infantile antics of Cecile. People can criticize "Cruel Intentions" all they want, but when it comes down to it, it is so very similar to 1988's Oscar-nominated "Dangerous Liasons" that it really is hard to nit-pick. The only major difference I can actually detect between the two, except for the obvious (such as the present-day time period and teenage characters), is that the characters in "Cruel Intentions" seem to jump more vibrantly to life. In retrospect, while watching "Dangerous Liasons" not long ago for the first time, despite the brilliant performances by Close, John Malcovich, and Michelle Pfeiffer, all I could really think about was telling the characters, "lighten up already!"