Drillbit Taylor gets many things wrong, but one thing it gets right is the casting of its three dorky high school students. In trying to find a beanpole, a pipsqueak, and a fat kid to absorb the sadistic wrath of a particularly sociopathic bully (Alex Frost), casting directors Juel Bestrop and Seth Yanklewitz didn't hire three handsome twentysomethings and "nerd them up" -- they hired Nate Hartley (16), David Dorfman (15), and Troy Gentile (15), each of whom is the hilariously perfect incarnation of his respective archetype. Gentile in particular earns laughs for his whip-smart attitude and rapping skills. Screenwriters Kristofor Brown and Seth Rogen are wise to make these characters (Gentile's Ryan is clearly a stand-in for Rogen) as much the protagonists as Owen Wilson's homeless grifter, because Wilson's part of the story is decidedly more artificial. Give Brown and Rogen points for the unusual decision to make the homeless community a focus of their movie, but then take away those points for their broad and jovial depiction of it. These indigent men, played charmingly enough by Wilson and Danny McBride, seem to have chosen homelessness as an extension of their free-spirited attitudes, rather than having homelessness thrust upon them by antisocial behavior, or some horrible addiction. If the story were just about Drillbit fleecing these dorks while operating as their half-assed bodyguard, that would be one thing. But then the film unwisely detours into Drillbit's redemption attempt as a substitute teacher at their school -- under the suspicious pseudonym "Dr. Illbit" -- where he romances a teacher played by Leslie Mann, producer Judd Apatow's wife. Everything related to Mann is hasty and perfunctory, although she manages to be as funny as ever. Drillbit Taylor just doesn't have the tools to be anything more than a minor peon in the Apatow empire.