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Billy Bob Thornton as Dr. P
Jon Heder as Roger
Jacinda Barrett as Amanda
Matt Walsh as Walsh
Horatio Sanz as Diego
Todd Louiso as Eli
Michael Clarke Duncan as Lesher
Sarah Silverman as Becky
David Cross as Ian
Luis Guzmān as Sargeant Moorehead
Ben Stiller as Lonnie
Directed by Todd Phillips
Roger (Jon Heder) is one of your typical film losers, a nice guy with no confrontational aptitude and underdeveloped social skills, the combination of which automatically make him a target for others like the weak lion that's kicked out of the pack to keep it strong. After having all of his clothes stolen by a pair of neighborhood toughs and being fired' as a big brother, he enrolls in Dr. P's (Billy Bob Thornton) class on how to be a man.
"School for Scoundrels" is one of those typical all-about-self-confidence romantic comedies, where the object of desire (in this case Jacinda Barrett) isn't so much a character as a trophy of empowerment. It's a formula comedy, which means it needs to be really funny to get over the fact that it's not actually about anything, and despite several openings for really dark comedy, "School for Scoundrels" isn't really funny. Occasionally chuckle-worthy, but that's about it.
Dr. P is your basic confrontational specialist, using intimidation to scare his students into adapting more assertive personalities, based on the idea that nice guys really do finish last, and which would you rather be, nice or first? Dr. P is an in-your-face unrepentant jerk who is not at all above lying, cheating and stealing to manipulate a situation to his advantage. Thornton should be perfect, but apart from some of his speeches on manliness, he often seems bored.
Roger is a natural at Dr. P's form of human interaction and quickly rises to the top of the class, eventually managing to score a date with his dream girl, who as typical for this type of movie has to come off as completely oblivious (until she's not) without seeming stupid. It's not the easiest thing in the world to do and Barrett pulls it off decently enough. Heder also manages to be decently charming, only occasionally falling back into "Napoleon Dynamite" patterns, but does come off as weak next to the more experienced comedians, particularly Stiller.
When Dr. P starts chasing Amanda (Barrett) on his own, Heder turns to Lonnie (Stiller), an old patient of Dr. P's who went through something similar and has a score to settle with the good doctor and his psychopathic assistant Lesher (Michael Clarke Duncan). Only Stiller and Duncan are consistently funny throughout and their scenes together are the best in the film. Unfortunately, there's not very many of them.
"School for Scoundrels" has some solid opportunities for real dark comedy, but blows most of them for maudlin romantic-comedy tripe, and the ones it does go for it never takes far enough. It's not bad, but it could have been better.