Three dorky teenagers starting high school want one thing – to make their first day their best.
Wade (Nate Hartley) and Ryan (Troy Gentile), guys who just want a good start, meet Emmit (David Dorfman) by standing up to Filkins (Alex Frost), the school bully. They also get to know each other much better once crammed into the same shirt.
After a week of similar hazing by Filkins and his croney, Ronnie (Josh Peck), the boys decide it’s time to hire a bodyguard.
Using an online advertisement, they attract everyone from a former bodyguard for Tupac ("it ain’t my fault he’s dead") to Ulitimate Fighter Chuck Liddell himself, finally settling on Drillbit Taylor (Owen Wilson) – a "home free" vagabond who deserted during the Gulf War.
Trained as a special ops soldier, he now lives in a small "strategic outpost" made of a box by a ravine and showers naked on the beach.
The boys, taken in by his persona, hire Taylor for a paltry sum (including Emmit’s bar mitzvah money) with a promise of more later.
Taylor, looking to make enough money to move to Canada, strings the boys along by cajoling them through a bogus training camp and teaching them "classic" techniques skimmed from movies.
Once his young students try to use his teachings, they get beaten up repeatedly by Filkins, who just won’t take it.
Wade finally confronts Taylor and asks about the claims he made of being there to protect the boys when they need it.
One thing leads to another, and Wilson’s character finds himself in school as a substitute teacher, hitting on Lisa (Leslie Mann), while Wade hits on Brooke (Valerie Tian), the Asian girl who caught his eye on the first day.
Once Taylor’s scummy friends rob Wade’s house, he realizes what really matters and starts getting his act in gear.
Once the audience can get past the embarrassment of reliving high school vicariously through the kids, they start seeing Wilson’s character’s true depth and finds a lovable fraud, who, through the efforts of three teenagers, realizes his whole life can change for the better.
Several in-jokes pepper the screen with cameos from old movies in the same genre, and Wilson’s clever ad lib makes the movie fun for those with an eye for cinema trivia, while everyone else can ride along with a storyline which isn’t overly complex, but which still holds some acting gems.
Contrary to Taylor’s belief that "you can’t polish a turd," he (and the movie) turn out to be far better than the viewer might first imagine.
