A review requested by Brian, with thanks to supporting Alternate Ending as a donor through Patreon.

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It's hard not to respect Cruel Intentions for playing its game so well. We have here the collision of a couple of trends in the 1990s. First, it's a teen soap, from right around the time that teen soaps were starting to get really horny. And there's none hornier than this that I can name, a film that luxuriates in talk about sex acts and lurid allusions and the spirit of step-sibling incest hovering over it all like a pervy ghost. It is, indeed, a full-on "do you know what your children are doing?" type of exploitation film, except where as those movies are using the veneer of moral panic to at least vaguely disguise the fact that they're basically just serving up titillation, Cruel Intentions celebrates its depravity. It's unmistakably proud of itself.

Second, it's one of the "classic literature goes to high school" movies that were briefly all the rage in the wake of 1995's Clueless, itself part of the broader classic literature vogue of the 1990s. And here's the miracle about Cruel Intentions: for all its gleefully nasty licentious edge, it remains perfectly within the spirit and the letter of the 1782 novel Les Liaisons dangereuses by Pierre Choderlos de Laclos. It's just trying to be a good modernisation - it just so happens that an unblinking close-up of two attractive women tongue kissing is within the spirit of a modernisation of that robust, mocking exhibition of Ancien Régime libertinism. Sometimes, you do indeed get to have your cake and eat it too.

The film was the feature debut - indeed, near as I can tell, the directorial debut - of one Roger Kumble, who also wrote the screenplay. While I would hardly go so far as to call it one of the great first features, or a sign that the filmmaker has a clear and intuitive understanding of the language of cinema (in fact, the film looks quite average, with cinematographer Theo van de Sande doing fine work in making the lavish surfaces look appropriately shiny and expensive, but otherwise remaining largely anonymous), there is a definite brashness and freshness to the proceedings that feel like the work of a filmmaker who has something he wants to prove. It's a lively film, appropriately so given the focus on teenage characters who are driven more by their hormonal energy and the individual pleasures of individual moments.

This shows up especially strongly in the performances, which have no right to be this good. The film has assembled a rather strategic mixture of variably recognisable young faces, headlined by Sarah Michelle Gellar, riding high on the cultishly adored TV show Buffy the Vampire Slayer, and still at this point looking to make her move into movies; her co-lead is Ryan Philippe, who'd been popping up in movies here and there (in fact, he and Gellar had already appeared together in the dreadful slasher film I Know What You Did Last Summer in 1997), but was still more of a pretty-looking That Guy than an actual draw. Reese Witherspoon was a lucky get, having just landed on people's radars several months earlier with Pleasantville, while her major critical breakthrough in Election was right around the corner. Joshua Jackson had been in a fair number of films the target audience would know fondly, but of course his big calling card was as one of the more-talented secondary leads of television's Dawson's Creek. Among the significant cast members, Selma Blair was the only more or less complete unknown.

A canny job of casting or not, that collection of people isn't precisely known for the quality of their acting - Witherspoon is probably the most talented name on that list, and she's still pretty inconsistent - so the one place we absolutely must give Kumble his due credit is that he got quite a bit out of them that was by no means guaranteed, and the passage of time has only made it clearer just how few tricks some of these people had. Which makes it all the more impressive that Philippe and Gellar, in particular, are so damn engaging and vibrant (Blair is actively bad, but that's mostly on the writing). Gellar, I'd say, has never been better, not even in her signature role as Buffy Summers: she is having an absolute blast playing the calculating, mercilless Kathryn Merteuil, a bored, hedonistic daughter of fantastic wealth in Manhattan.Philippe plays her stepbrother Sebastian Valmont, and while the story does him dirty by asking him to start feeling real human emotions partway through (the film's one misstep as an adaptation: this face turn is there in the source material, but the movie over-emphasises it, and starts foreshadowing it much too early), he's matching Gellar's oversexed boredom line-for-line in the opening, if not her great self-satisfied villainy. Both of them are going for unabashed camp, and in their different emotional registers, both are great at it: the material is being re-conceived as melodrama, but this turns out to be a very good fit for it, especially since it already looks slightly like an extremely posh soap opera. At any rate, Gellar's hambone Machiavellian turn is so utterly fearless and showy that there really isn't a single scene of the film that she's in that isn't completely delightful. It's an indulgent performance for a film whose pleasures are largely indulgent.

The plot is a simple matter of two monsters keeping them amused: Kathryn and Sebastian plot to sexually destroy the lives of young women they don't admire for whichever reason, with Kathryn hoping to ruin the reputation of Cecile Caldwell (Blair), an unreasonable idiot, to get revenge on an ex-boyfriend, with Sebastian hoping to deflower activist virgin Annette Hargrove (Witherspoon) just to prove that he can do it. The question of whether Les liaisons dangereuses is a social satire or just high-minded literary is, I believe, still open, and Cruel Intentions matches this aspect of its source material. Maybe not so high-minded, admittedly: a film that involves this many teenage characters (albeit played by visibly non-teenage actors) discussing explicit sex acts is clearly going for provocation first, titillation second (or maybe the other way around), and there's not much about it that's artful at all; certainly, there's damn little that's subtle. But for all that, there's an irreducible core of social commentary that still shines through. The idle rich are not held up for any admiration in this film: Kathryn is openly evil and proud of it, Sebastian is seemingly a literal sociopath, incapable of understanding that other people have inner lives, Cecile is an almost literally dysfunctional idiot. Annette is the only person who's done much of anything, and she's the only character the film expect us to like at all at least until the somewhat unpersuasive shift where she encourages Sebastian to become a good man. It's not calling for revolution: it too hungrily loves the surfaces of the Manhattan upper classes for that. But it also makes it impossible to think about those surfaces, or these beautiful young people, or the whole matter of late-'90s teen soaps, without seeing the amorality underpinning them, by exaggerating that tendency to the point of outright nihilism. It is a pitch-black, nasty-hearted movie, and it makes no attempt to moralise; but it doesn't for a moment pretend that we should like these characters, root them, or feel anything but delight when they fail. This is maybe the nastiest bit about it: it views Kathryn and Sebastian the way they view everyone else, and makes it far too easy to completely slide into their depraved, decadent headspace. It's not a comfortable place to be, but the film sure does make it out to be disreputable fun.