Wilson plays Dupree, consummate party boy and friend to Carl (Matt Dillon). The film opens in Hawaii, where Carl is fixing to marry Molly (Kate Hudson), before the judgmental eyes of her bizarre father (Michael Douglas). Dupree is a goofball ne'er-do-well who seems a little worried about his best bud tying the knot. When Carl returns from his honeymoon, he discovers Dupree was fired for taking time off work for the wedding, and he naturally feels responsible. He invites Dupree to spend a few days at his home while he gets back on his feet, and this is where the trouble begins.
Molly is not thrilled about Dupree's presence in her new home, and she's justified in her pain. Dupree clogs up the downstairs toilet, and then leaves his post-buffalo-wing-binge stench in the bedroom toilet, failing to inform the couple of the mess he's left behind (they find it in the morning). Dupree is impossibly rude in this film, ordering HBO without permission, sleeping nude on the couch and eventually burning down the living room.
The Dupree character is too annoying, brainless and revolting to be even remotely funny. Wilson's surfer-boy, dimwitted shtick can be awesomely tiresome when the material isn't up to snuff, and this is his worst film yet. He's priceless in the Wes Anderson films (especially Bottle Rocket) and pretty good when paired with the likes of Vince Vaughn and Ben Stiller. But here, where most of the laughs fall on his back, he comes off as a desperate comedian.
Most ludicrous is Dupree's infatuation with an unseen librarian named Mandy who Molly hooks him up with, a date that culminates with him lubricating Mandy with butter on the living room couch. Dupree pines for Mandy after their one date, something that could be funny if minimally explored, yet the screenplay makes him a total psycho regarding her. This is just another idiotic script element that gives Wilson too much stupidity to overcome.
Dillon, so funny clowning around in There's Something About Mary, is forced to play things mostly straight in this film, and it's a boring performance. Hudson, who hasn't taken part in a decent film other than Almost Famous, continues her remarkable slump. She can only get so much mileage out of her one good movie, and she might need to get somebody different to sort through her project opportunities.
While the Dupree character is rather preposterous, Douglas is full-blown ridiculous in this movie. His is the typical disapproving father-in-law, until he starts demanding that his new son-in-law take his wife's name and get a vasectomy. There's never really any explanation for why Douglas' character is so mercilessly evil in this film, and none of it is funny. It's just sort of cruel and ugly. The social crimes the guy commits shouldn't be redeemable, yet the script asks you to forgive.
If the sights of Owen Wilson getting hit by a car, sleeping naked on a couch or taking a major digger during a skateboarding run seem excruciatingly funny to you, have at it. You, Me and Dupree is Hollywood comedy at its worst, a movie-by-numbers fiasco that insults everybody who watches it, and everybody associated with it.