We gave it a B-
Remember the shaggy-haired stoner, all fog-brained earnestness and Valley boy dude-speak? How about the corporate weasel, who hid his killer moves beneath a heat shield of mock-gregarious ”Hey, guy!” irony? Put the two together, and you have Owen Wilson, a slacker for the cutthroat age.
With his surf-bum hair, his broken nose, and that voice that seesaws up and down, grinding out each word with cracked, pained sincerity, as if he were trying to talk while holding in a bong hit, Wilson has always led with his sexy-foolish, natural-man charm. Yet if the voice is baked, the mind is clear, and it’s working overtime, usually for himself. In Wedding Crashers, he was perfectly cast as a scoundrel who used his soulful ”honesty” to hustle women into bed, telling them what they wanted to hear. His actions may have been deplorable, but what made them so funny was that the romantic lies seemed to trickle right out of Wilson’s good nature; it’s as if he lived to please, and couldn’t help that everything happened to work out his way in the process. No wonder Owen Wilson is a star: He’s the first actor of his generation to turn innocence into sleaze, then back into innocence again.
From the moment Wilson appears as the free-spirited screwup of You, Me and Dupree (yes, he’s Dupree), landing in a yellow prop plane in Hawaii, the movie uses his crooked smile and craftier-than-it-looks faux doofishness as a subtle form of one-upmanship. Dupree is set to be the best man at the wedding of Carl (Matt Dillon), a land-development executive who’s his oldest pal, and Molly (Kate Hudson), a sunny grade-school teacher. The two enjoy an idyllic wedding, but back home, before they have a moment to savor their lives as newlyweds, in walks Dupree, toting a moose head and a ukulele (are you laughing yet?), desperate for a place to crash after losing his job and his apartment. It isn’t his fault, of course — nothing ever is — but we can see that he’s the sort of infantile, moonstruck underachiever who can’t get a career going because, deep down, he doesn’t want one. He just wants to drink beer and eat nachos and watch a big TV and pretend he never has to grow up.
You, Me and Dupree isn’t a very funny movie (it preaches nonconformity in the rote style of an overlit sitcom), but Wilson, at least, keeps it afloat. The shrewdness of his performance is that he makes Dupree adorable and overbearing at the same time, so that you can’t separate the two. Carl and Molly start out united in their disdain for Dupree’s benignly reckless, me-first antics: the sight of his bare butt poking out from the rumpled couch covers, his ordering of premium cable TV, the fact that he seduces the librarian at Molly’s school — a nice girl! a Mormon! — by doing nasty things with butter on the first date right in their living room, just before he accidentally sets the place on fire. Before long, though, his hedonistic indolence begins to cast its spell. As a man in his 30s who still lives like a couch-potato jock out of college, Dupree is destined to be likened to such recent child-man slobs as Matthew McConaughey in Failure to Launch and Vince Vaughn in The Break-Up. But whatever observations the movie has to make regarding the Gen-X tendency toward arrested development, what we’re really watching is a less witty version of What About Bob?, with Dupree as the innocent invader who’s been placed on earth to drive Carl, the humorlessly toiling, overly rational middle-class breadwinner, crazy.
As Dupree, a saintly pest, lets his charm flow over Molly (he even writes poems), inviting her to enjoy life in a way that her systematic husband can’t, he becomes Carl’s nightmare: the slacker id who succeeds by doing nothing, seducing the world simply by letting it pass by. You, Me and Dupree is a three-headed comedy in which the situation really goes all the way back to Green Acres, where poor, uptight Oliver Douglas was driven to frothing fits by his wife’s fondness for the loopy neighbors he couldn’t abide. If only this movie were half as hilarious.
You, Me and Dupree would have had more bite, more comic anger, if it didn’t stack the deck by giving Carl an external reason for losing his grip: His boss is his father-in-law (Michael Douglas, clenching his teeth as if they were receiving radio signals), who happens to take a psychotic delight in abusing him. Matt Dillon is miscast anyway — by temperament, he’s close enough to slacker nonchalance that we don’t quite buy him as a yuppie control freak. The joke, of course, is that it’s really Owen Wilson who’s in control. He can’t play the dazed rogue forever, but for now he’s the happy master of that domain.