With an identity crisis always pushing it forward, You, Me, and Dupree is inconsistently funny. At times it’s a hard drama, over the top goofy comedy, and then a basic relationship tale. It feels disjointed, as scenes fail to flow together, yet there’s still enough material here to laugh at.
Owen Wilson is the star here, playing the lovable Dupree, the down on his luck slacker. Matt Dillion plays Carl, his best friend. Carl’s new wife is played by a gorgeous Kate Hudson, generally taking the role of the sympathizer.
Dupree lands on hard times, and moves in with Carl for what should be a brief period. This sets off the expected conflicts, especially as Dupree attempts to relive his younger days. Laughs take a long time to develop, and are spaced wide apart. The brief payoff is usually brief, though enough to carry the film until its next event.
This is a movie at its best when Owen Wilson is allowed to take over. Carl ends up overloaded at work, and this creates a separate conflict that simply isn’t that entertaining to watch in either a comedic or dramatic way. These scenes, even though Michael Douglas handles the role of Carl’s boss and in-law nicely, don’t feel like they fit. They give the film a hard edge, which negates some of the comedy.
It’s a shame too, as the simple premise of Wilson’s character hanging around, creating awkward situations, and attempting to find work would have been enough. Spinning into the relationship downfall and corporate power struggles leads it into a path that it can’t find a way out of. In the end, it feels as if the comedy is secondary.
That said, this is still worthwhile to watch, simply for Dupree’s antics. It’s a great character that you root for to finally find some success. You’ll need to sit through some uglier spots to find the fun, yet you’ll still come away happy. 
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