Owen Wilson as Drillbit Taylor
Troy Gentile as Ryan
Nate Hartley as Wade
David Dorfman as Emmit
Alex Frost as Filkins
Josh Peck as Ronnie
Danny R. McBride as Don
Leslie Mann as Lisa
It's the old coming of age story – adolescents begin transition into adulthood, adolescents are mercilessly bullied due to accompanying social and physical awkwardness, adolescents hire a washed up, homeless former Army Ranger (Owen Wilson) to be their bodyguard.
Hmm... stereotypical teenage characters with no resemblance to actual teenagers, absent parent figures utterly clueless about their children's lives, a full grown man-child standing-in for the parents and learning to take responsibility for his own life in the process... if I didn't know better I'd swear this was a John Hughes movie (or at least one of his limitless imitators), and waddya know, according to the credits "Drillbit Taylor" comes from an original Hughes story, albeit through the lens of the genuinely talented Judd Apatow ("Knocked Up") and his various cohorts.
No matter how talented they are, there's only so much Apatow and friends can really bring to such a tired idea, though Apatow himself has retreated to a producing position, leaving the writing in the hands of Seth Rogen, who after the success of "Superbad" has more than proven himself in this area. At first glance there's not a few things in common between the two – the skinny, awkward friend (Nate Hartley), the portly, mock-streetwise friend (Troy Gentile), and the unbelievable (and I mean that literally) dorky Emmit (David Dorfman), all desperate to remake themselves as socially acceptable on the first day of high school. It sounds right up Rogen's alley.
It's unfortunate then that, apart from two or three genuinely unexpected laughs, there's not much to recommend it. Most of it is the same high school comedy we've been watching since Hugh's heyday 20 years ago. Everyone is either popular and cruel (because in teenager-land one de facto means the other) or awkward and misunderstood, and thus fair game for the popular kids. And not a single recognizable human beings among them. Why are any of these people behaving the way they are, why is the bully a bully? There's no telling. And I actually knew someone just like Emmitt in high school, and even he wasn't like Emmitt.
We're expected to just understand the way these movies are supposed to be and accept the rules they use, which is fair enough. It's hackery of the first order, but fair. Within those rules, the adults the kids are supposed to be able to rely on (parents and teachers) are either absent or worthless, so the kids are forced to find their own parent figure, which brings Drillbit Taylor into their lives.
He also fits the Hughes mold perfectly, a basically good person with some serious personality flaws. Drillbit is supposed to be where the real comedy comes from, fooling the kids until he gets what he wants from them (money) and everyone else he comes in contact with as he dives head first into social situations he's not at all prepared for, masquerading as a substitute teacher at the kids' school so that he can, theoretically, keep an eye on them. Unfortunately, the jokes are so anemic that even taken just for themselves they're not particularly funny. It really requires of feat of incredible screen charisma to pull this off and actually make it work, and Wilson's just not up to it. Wilson can be a decent actor in the right hands, but director Steve Brill ("Heavy Weights") never tries to get out of his comfort zone and it shows in every moment of "Drillbit Taylor."
Except for a few genuinely unexpected laughs, so few you can count them on one hand, "Drillbit Taylor" is pretty dull. Not particularly bad, just dull.