Taken on its own, Drillbit Taylor is a film that's too grounded in reality to be that funny. Considering the pedigree involved in writing the project, add the phrase "Exceedingly disappointing" to it also. You see, John Hughes came up with the story, and Seth Rogan co-wrote the screenplay. No, this isn't an Ethan Cohen vs. Etan Cohen situation here, these are the John Hughes & Seth Rogan that you know and love. So how did this film go so wrong?
First off, the story. The plot revolves around three bullied kids hiring a bodyguard to protect them, except the bodyguard is actually a homeless person, and doesn't really have any credentials to be bodyguarding. Sound familiar? It should. The plot derives cliches from every bully plot or sub-plot in movie history, every character pretending who they're not, then being found out plot or sub-plot you've ever seen, and a myriad of other random high school cliches. And since the script was co-written by Seth Rogan, who also did Superbad, you can derive a dozen similarities to that movie as well. In fact, in that respect, Drillbit Taylor seems like the prequel to Superbad. There's the tall, geeky kid that has trouble with the ladies. There's his smart-mouthed friend, who also happens to be chubby. And they even have their third member, who isn't really a core member, but can be helpful/crazy when you need him to be. But Michael Cera, Jonah Hill & Christopher Mintz-Plasse these kids aren't. They're bad actors, and they sell little if anything about their characters. The adults are good actors, but with the exception of Owen Wilson and maybe Danny McBride, everybody is reduced to little more than cartoon characters. In one scene, the bully charms all the parents and the school principal with a stupid joke and a smile, and everybody acts like he was Jesus Christ. Granted, this fits into the cliche in these films that adults are stupid and you must take it upon yourself to stand up for yourself, but that's Home Alone logic. And at least in that film, the adults weren't total buffoons.
But that being said, the highlight of the film, and the only real reason you should think about watching this film is Owen Wilson. Wilson brings a certain charm to the character and makes the most out of a poorly-written character that's story-arch is a little bit non-existent. Wilson's character starts off as a greedy jerk, then turns into a nice guy, with the implication of one scene being the only explained reason. Then there's the fact that Drillbit can't really fight, then turns into a kicking bad-ass in the one ending scene that makes of the film's DVD cover.
Which brings me to this: The film isn't that funny. There's some gags that work, and the charms of a few of the actors make jokes more funny than they really are, but there simply isn't much here to laugh at. This is mainly due to the fact that there's little place for true humor in the story. Why? Because the bully is an unrelenting and dangerous psychopath that threatens people and commits bodily harm to them with a freakin' samurai sword. Thus, the confrontational scenes are utterly brutal to watch. It's like watching a mouse crawling into a lion's cage. You admire its perseverance, but you known that the Lion has the ability and the desire to shred such a cute thing. It's not funny, it's just uncomfortable and scary. The story tries to add humor around these situations, but every one of them falls flat. Especially the ones that involve topics such as balls. Oh, and if you've ever had past experience, or have been traumatized by a bully, you'll be traumatized by watching this film. I felt traumatized and I haven't even been in that situation.
Overall, if you're a HUGE Owen Wilson fan, then check out this movie, and you'll find something you like. Otherwise, skip it like it's a fat girl at the prom dance. There's not much to like, there's not much to think about, there's not that much to laugh at, and in the end, you just feel bad.