As if just being a male meter maid didn't already set you up as the punch line of somebody's joke, New York City meter maid Roger (Jon Heder) is, in every aspect of his life, a veritable humiliation magnet. Wimpazoid Rog is such a born loser that he winds up paying the parking fines for the jerks he tickets, and even the little kid he's sponsoring in the local Big Brother program rejects him. Then there's that beautiful neighbor (Jacinda Barrett) he can't even get up the nerve to ask out.
All of which prompts Roger to enroll in a highly unconventional self-esteem boosting program run by a foul-mouthed crypto-fascist known as Dr. P (Billy Bob Thornton, once again basically recycling his Bad Santa/Bad News Bears uber-jerk shtick). Dr P's "confidence building" tips encourage the worst sort of behavior (Rule #1: Lie, lie and lie some more), and the bulk of School for Scoundrels amounts to a series of not-particularly amusing episodes involving Roger and his fellow wimps attempting to unleash their inner assholes.
What minimal fun the movie has to offer trickles away during the second half, when Roger learns his lessons too well, prompting the highly competitive Dr. P to knock him down a notch by putting the moves on his new girlfriend. The spectacle of the two men locking horns is more mean-spirited than interesting, and, worse, it's rarely very funny — to the point that, by the film's end, director Todd Phillips (Road Trip, Old School) can't even seem to decide whether he's selling us a comedy or some sort of vaguely serious thriller. School for Scoundrels assembles a solid supporting cast only to leave them standing around with little to do, and Heder, the Napoleon Dynamite golden boy, is even less engaging here than he was in The Benchwarmers, putting his big screen future seriously in doubt. There's an obligatory cameo by Ben Stiller in there somewhere as well.
