Charles Schine (Clive Owen) rides the train to work. He and his weary-seeming wife Deanna (Melissa George) share a quiet, dispassionate partnership in the Chicago burbs, expending most of their emotional energy on looking after their sweet, diabetic, occasionally near-death daughter Amy (Addison Timlin). They’re so focused on this noble cause that, as Amy notices, they don’t even kiss when they leave for work in the morning. He helps Amy with her homework, mom helps her with her shot, and Amy helps with the levity (“Who wants to live forever, right?”). And with that, dad’s on his way, running to the train, in the rain, all bedraggled and woebegone when he misses it.
And so begins Charles’ descent. While he is, as the film’s title suggests, Derailed by his encounter with Lucinda, he’s also stuck inside one of those “thrillers” where one semi-smart choice would turn the entire plot around, and Charles — apparently much less intelligent than he appears in his first few minutes on screen — does exactly the wrong thing at every opportunity. First off, he takes up the high-heeled, black-stockinged come-on from Lucinda (Jennifer Aniston, not quite, as the ads trumpet, “as you’ve never seen her”). They meet cute, she mixes rudimentary mystery with perky come-hitherness, and he’s hooked.
Though he knows better, Charles sets up a lunch, they lie to their spouses, get in a cab, and head to a hotel, all the while wondering whether this is really what they want to be doing (you see this in close-ups of Lucinda looking… whatever it is that Aniston looks when her role calls for “worry”). When at last they make their way through still more rain and more bedragglement into a seedy joint where they get a room for $46, they’re barely underway when a scary thug named LaRoche (Vincent Cassel) busts in their room with a gun.
The villain goes through their wallets, chides Charles for cheating with this “fine piece of ass,” then beats him bloody, and looks about to rape Lucinda as Charles goes under. While all this is odd, Lucinda’s ensuing behavior is downright bizarre. Insisting that her husband will take her little blond daughter from her, Lucinda makes Charles promise not to tell the cops or his wife. And of course, he agrees, feeling all guilty about the rape that went on during his wussy unconsciousness.
While all this business would constitute plot in another movie, here it’s just set-up. Within hours, LaRoche calls with a blackmail demand. Soaking in his tub with his bruised face sad and murky, Charles agrees, after a little hissing that LaRoche should never ever call his home again! And oh yeah, he soon figures out, Charles isn’t going to be able to keep up his toughness, especially when LaRoche keeps asking for money. And to whom does he turn for answers? The black guy.
This guy’s name is Winston (RZA), and he delivers the mail in Charles’ office. As he’s an ex-con (with a 4.0 GPA in high school), he has an understanding of brutality that is, at least for now, quite beyond Charles’ own. When Charles asks him what prison is like, Winston looks sage as only the RZA can: “Prison’s like walking a tightrope,” he says, then essentially admits that he killed a man to survive: “When your back’s up to the wall, you gotta do what you gotta do.” Charles agrees again, at least as far as he can comprehend the dire meaning of this assessment. What, exactly, does he gotta do?
What follows devolves even more feebly into silly-plotting. The scheme gone wrong leads to the introduction of a couple of other black guys, dogged and painfully named Detective Church (Giancarlo Esposito), who also happens to be related to Winston, and LaRoche’s second, Dexter (Xzibit, equipped with scary “street” affect and much goofier dialogue than he runs when pimping rides). Charles finds his inner thug after he’s made what appears to be a series of profoundly wrong decisions. His sudden ingenuity and action heroics hardly make up for the rest of his bad judgment, or the film’s ancient moralizing (i.e., adultery is bad).
While it’s easy to make title-related jokes about Derailed, the truth is, that the film’s troubles don’t begin partway through. Problems inhere in its grounding in stereotypes, from the hardworking, well-meaning white folks in the burbs to invading French villain to the uses and abuses of black criminals. While RZA and Xzibit deliver their own delights as performers, being infinitely subtler than their roles demand, their characters’ aggression and victimization are of a piece, and left to the white guy to sort out.