Bad Movies We Love: Cruel Intentions

According to movies, teenagers enjoy one activity: scheming. Who could disagree? I schemed as a high-schooler. Certainly. If by "schemed" you mean "ate Wheat Thins for dinner, wore Kohl's cargo shorts, and cried at Natalie Imbruglia lyrics," which you do. Cruel Intentions perpetuates the myth that teenagers inhabit more exotic, scheme-filled lives than Danny Ocean, and its melodrama predates the emo generation by an impressive half-decade. Great! Star Reese Witherspoon may tame pachyderms in Water for Elephants this coming weekend, but in Cruel Intentions she conquered the more formidable "trunk" of Ryan Phillippe, which should be its own Big Top spectacle.

Sarah Michelle Gellar and Ryan Phillippe (who we discussed last week in I Know What You Did Last Summer) are evil step-siblings, Kathryn and Sebastian, who regularly team up to manipulate peers, lovers, and -- from the looks of it -- J. Crew clerks. Kathryn wants to get back at moron Cecile (Selma Blair) for capturing the attention of Kathryn's ex, so she enlists Sebastian to schtup Cecile and corrupt her innocence. Meanwhile, Sebastian wants to sleep with the self-proclaimed virgin Annette (Reese Witherspoon), and if he succeeds at the unlikely task, hard-to-get Kathryn says she'll sleep with Sebastian and let him "stick it anywhere." If he doesn't bed Annette, Kathryn wins his Jaguar. A regular bunch of Bradys, this family.

Cruel Intentions is based on the 18th century epistolary novel Les Liaisons dangereuses (which also spawned the movie -- watch this -- Dangerous Liaisons), but it's mostly based on the original idea of making rich teens the most diabolical horndogs alive. When Kathryn wants to manipulate Cecile into becoming a slut, she teaches her how to kiss with a passionate, slow-motion makeout. It's the most serious plea for an MTV Movie Award you've ever seen. Aside from the career of Michael Bay.

In case you're keeping track, this makes two Bad Movies We Love so far for Reese Witherspoon (with S.F.W.), two for Sarah Michelle Gellar (with I Know What You Did Last Summer), and three for Ryan Phillippe (with 54 and I Know What You Did Last Summer). What is it about Ryan Phillippe and his connection to lovely, awful films? Ah yes: He tries so hard. Ryan Phillippe's subtle acting choices range from "scowling 100% of the time" to "screaming mid-sentence," and those decisions often make a Bad Movie We Love happen. In Cruel Intentions, his bastardliness and butterscotch curls are the most clear emblems of the film's insanity. Bastardliness and Butterscotch Curls could've been the original title, in fact.

Selma Blair. How to describe this pouting thing? Here, she plays a kooky pollyanna who is too dumb to root for, and too unfunny to be tolerated. When Sebastian goes down on her in another of his ingenious manipulations (or something), she reacts like a two-year-old discovering her own navel. Kind of nasty! Better just to love her uptight mother, who gets 25 lines and a Chanel wardrobe.

Did you guess? You should've. The phrase "25 lines and a Chanel wardrobe" is reserved for Christine Baranski's filmography. She's also making her second Bad Movies We Love appearance, thanks to Addams Family Values. We should make a chart now.

I've seen Cruel Intentions three times now, and it's always easy to forget the soulless magnificence of Joshua Jackson's early scene as a gay trickster who sleeps with a closeted straight guy and lets Sebastian cash in on the blackmail. Look at that face. He's got the Commedia dell'Arte super-expressions to launch a mime career. Or at least Pacey-Con.

Oh no, another Oscar-winner is wrapped up in this business too. That's Louise Fletcher as Sebastian's aunt, and she's just as malleable and clueless as all of his pawns. Please. Imagine tony Mr. Phillippe handling the wrath of Nurse Ratched. That's a short story and/or fever dream I will soon create.

Now, the final scene in Cruel Intentions is a prissy Mean Girls-esque moment of backbiting accompanied by the Verve's "Bittersweet Symphony" (because nothing is better in a Bad Movie We Love than an overly literal soundtrack), but before we hit that off note, we're treated to one of the most dubious scenes of the past 20 years. Sebastian, who fell in love with Annette, brawls in the streets with Cecile's adoring violin teacher (Sean Patrick Thomas). Kathryn had informed him about Sebastian's tryst with Cecile, like a jackass. As their scuffle expands into a busy lane of traffic, Annette arrives and tries to break it up. Bad idea, June Carter Cash! Sebastian dives to save her as a car almost runs her over, but he gets himself killed in the act. It's such an outrageous and senseless death, you'd think you were watching I Know Who You Ate Out Last Summer.

If you still feel sad about the destruction of Sebastian and Annette's courtship (and I'm sure you do, since all their scenes were paired with Counting Crows and Aimee Mann songs), I suggest you try something. No, not watching the prequel or the sequel, fool! I'm talking about revisiting this scene, one that indicates we're dealing with the most despicable romantics alive.

"You mean nothing to me! You were just... a conquest!" Signed, Ryan Phillippe to this movie, 1999.