Three freshmen arrive at high school with nothing in common except a target painted on their backs: chubby, motor-mouthed Ryan, skinny and anxious Wade, and tiny, oblivious Emmit. Within a day they have attracted the undivided attention of Filkins, a bully whose menace runs well past the usual locker-shoving, and his sidekick Ronnie. With no teacher, parent or administrator willing to intervene, the boys do the only thing that makes sense to fourteen-year-olds with pooled allowance money: they place a classified ad for a bodyguard.
The man who answers is Drillbit Taylor, who introduces himself as a decorated ex-Army Ranger and is in fact a homeless drifter working a con. He sizes the boys up as marks, takes the job for the cash and whatever else he can carry out of their houses, and begins delivering self-defense wisdom of extremely questionable provenance. To keep an eye on his clients he talks his way onto campus as a substitute teacher, where he catches the attention of a colleague, Lisa, and finds himself maintaining a second fiction on top of the first.
What starts as a grift settles into something stickier. The boys begin to trust their fraudulent protector, Drillbit starts behaving like a man with responsibilities, and the escalating war with Filkins moves toward a confrontation that neither a con nor a classified ad can talk its way out of. Directed by Steven Brill, produced by Judd Apatow and built from an unfinished story by John Hughes, the film is a bullied-kid comedy about what happens when the person who finally protects you has nothing to protect himself with.
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