It's a good idea, and Phillips gets some of it right. Rather than take the lesson to completion, however, he proves that, as a filmmaker, he is shy and timid himself. I steeled myself against cliché from the get-go, as School for Scoundrels opens with a montage of its main dweeb, Roger (Jon Heder of Napoleon Dynamite fame), getting out of bed and getting ready to the tune of Bill Withers singing "Lovely Day." Is there a lazier music cue out there? It's seems in particularly bad form after the song was used so well in Roll Bounce. It's over, leave it alone.
Thankfully, things immediately improve once we get out of Roger's apartment. Roger is a parking enforcer, and when he gives two thugs a ticket, they chase him down in his little meter maid mobile, pursuing him on foot faster than he can drive. The confrontation is amusing, and it sets up the meekness of Roger's character and his condition where he has panic attacks and faints. It's also just the beginning of Roger's colossally bad day, and after suffering one humiliation after another to the point where he thinks he can't take it anymore, he is rescued by his friend Ian (David Cross, "Arrested Development"). Ian turns him on to an ultra-secret school where a dastardly character named Dr. P (Billy Bob Thornton) teaches losers to be winners. Not just winners, but kings of the jungle, lions who always get whatever they want.
Of course, Roger wants a girl, his neighbor Amanda (Jacinda Barrett, The Last Kiss). After a few sessions with Dr. P and his scary sidekick Lesher (Michael Clarke Duncan, Sin City), including a hilarious paintball war and some funny scenes where students are forced to cause confrontations in their everyday lives, Roger gets up the gumption to ask Amanda out. It works, and following Dr. P's rules for lechery on their first date, he does pretty well for himself. It moves him to the head of the class.
Which is when Dr. P gets competitive, and when the movie should really take off. Posing as a surgeon, Dr. P decides to steal Amanda for himself, beginning a battle of wits between teacher and pupil. It starts off strong, with hurled insults and well-aimed tennis balls, but the schemes quickly lose their teeth. When you want the movie to get nasty and for Billy Bob to bring the sort of grimy sleaze that made him such a hateful hoot in Bad Santa, the film turns emotional on us. It should get meaner as it goes, not more schmaltzy.
A big part of the problem is Jon Heder. I'm not sure there is anyone less funny than him. The guy is stiff from the bottoms of his feet to the top of his head. He tries for exaggerated expressions, but he just looks like an idiot in a rubber mask. His supporting cast attempts to hold him up, but they're too far out of Heder's league, so instead he gets out-acted left and right by the likes of Sarah Silverman, Horatio Sanz, and Luis Guzman. Ben Stiller pops up in the kind of cameo that he trades off with Will Ferrell from movie to movie, and his portrayal of a student previously broken by a war with Dr. P will seem familiar to anyone who saw him as the 12-step stepdad on "Undeclared." Add to that the dead-on-arrival gags about being anally raped by Lesher that keep popping up, and the mid-section of School for Scoundrels sags low. There is a bit of a rebound in Roger's last ditch effort to pull Amanda from Dr. P, but it's too little too late.
For a film about guys learning to be less wussy, School for Scoundrels is too wussy itself. Todd Phillips needs to get his own butt back to class and sit down with some DVDs of Animal House and Caddyshack to refresh his memory about why these movies have stood the test of time and become the high bar for dirtball humor. School for Scoundrels is merely spitwad by comparison.