DRILLBIT TAYLOR (Steven Brill, 2008)
Gangly Wade (Nate Hartley) and chubby Ryan (Troy Gentile) are stoked for the first day of high school. They can carve out new, cool identities for themselves, that is until they show up wearing the same shirt and stand up for tiny, bullied Emmit (David Dorfman). These fashion and social blunders put them on the radar of Filkins (Alex Frost), the school's most fearsome bully. Filkins is emancipated from his Hong Kong-dwelling parents and snookers Principal Doppler (Stephen Root) with his Eddie Haskell act, meaning he is answerable to no one.
In DRILLBIT TAYLOR the boys determine that their only means for survival is to hire a bodyguard. They interview many but can only afford the curiously named Drillbit Taylor (Owen Wilson). Claiming to have been discharged from the Army for going beyond the permissible limits of heroism, Drillbit talks up his fighting and covert ops expertise to earn their trust. Whether he is telling the truth is beside the point. The homeless beggar is only interested in scrounging up a few hundred dollars to get him to the better life he believes is waiting in Canada.
Drillbit intends for the bodyguard arrangement to provide a quick monetary gain but discovers that he can string along the boys for much more. He holds impromptu self-defense lessons that he makes up as he goes along. To keep their suspicions down, Drillbit infiltrates their school using a substitute teacher's guise, which has the side benefit of attracting a pretty English teacher (Leslie Mann).
Produced by Judd Apatow and co-written by Seth Rogen, DRILLBIT TAYLOR has a been there, done that quality reminiscent of SUPERBAD if it were much tamer and less funnier. The character names may be different, but these types are mirror images of Michael Cera, Jonah Hill, and Christopher Mintz-Plasse. It's very easy to envision those actors' younger selves as Wade, Ryan, and Emmit. Although not a prequel in any way, DRILLBIT TAYLOR is essentially the unofficial bookend SUPERBAD: FRESHMAN YEAR and a sign of diminishing returns from the Apatow brand.
Ultimately DRILLBIT TAYLOR lacks enough fresh material with the boys to sustain interest for the stretches when their bodyguard is bumming around off-screen. Nothing distinguishes their ordeals from the zillion other teen comedies in decades past. Perhaps that shouldn't be surprising since John Hughes gets a story credit under the pseudonym Edmond Dantes.
Yet for as overly familiar much of DRILLBIT TAYLOR is, Wilson salvages a good deal of it with his trademarked space case shtick. The lines he delivers aren't inherently funny; it's how sunnily and seriously he speaks them in his lilting voice that makes the words humorous. The Zen cowboy/mystic surfer routine is fitting for a script that doesn't tether the character to the world or this particular cinematic one. Drillbit floats in and away when the spirit moves him, leaving the bulk of a film named after him to the three boys he's supposed to be protecting.
Where Wilson struggles, though, is in defining a character that the writers don't see clearly. Is Drillbit looking to exploit the kids, or does he truly like them and take their safety to heart? Is there something darker spinning in his head, or is he an amiable bum with a severe lack of motivation? DRILLBIT TAYLOR suggests all of these as it flip-flops to an ending that opts for the softest landing. The film could have cut loose more if the writers decided Drillbit doesn't care at all or is a mother hen. It's safer in the school hallways to stay neutral, but in comedy a side needs to be picked.