Can we all finally agree that Owen Wilson has jumped the shark? Not only is he far from his days as primary collaborator of hipster icon Wes Anderson, not only has he become the most mainstream of stars thanks to Wedding Crashers, but now he's starring in an honest-to-goodness middle-of-the-road rom-com with notorious career-bungler Kate Hudson. Bottle Rocket fans, get set to be appalled.
Actually, You, Me and Dupree isn't even a genuine romantic comedy, since the couple that ends up with the romantic obstacles, saintly teacher Molly (Hudson) and workaholic suburban planner Carl (Matt Dillon), gets married at the beginning. Dupree (Wilson) is the best man, and soon he finds himself, in the manner of all affable cinematic layabouts, jobless, homeless and loveless, and ends up crashing on Molly and Carl's couch days after they return from their honeymoon.
Thus follows everything you've seen in the trailer and not much else. Dupree is messy, lazy and inconsiderate, and he drives the clean, composed Molly crazy. That is, until about halfway through, when it feels like someone did a drastic rewrite, switching gears from a story about a nasty houseguest to one about a guy paranoid that his best friend is stealing his wife. None of the characters is sketched clearly enough to warrant any sympathy or involvement; Hudson has done this role so many times that she could play it in her sleep, and quite possibly did.
Wilson is also playing the same hipster doofus part he always plays. The problem, as Carl tells Dupree after Dupree bemoans his status as a lovable loser, is that he's just not that lovable. In short, Dupree is kind of a dick, and by the time Carl blows up at him, he's rather justified.
Then there are the tired gender politics, in which every man is a beer-drinking sports fan and every woman an emasculating harpy. In the end, nothing is solved but nobody seems to care, and Dupree, like Wilson, is left a populist hero whose dopey catchphrases inspire the masses but are meaningless.