There' an under-discussed subgenre in comedy films that we like to call QOCWF, or "quirky outsider co-inhabits with family." You've undoubtedly seen some of these before. Mr. Nanny, Hulk Hogan' 1993 flick, is one. So is 2003' Dickie Roberts: Former Child Star. There are many more, and most of them are similarly atrocious. You, Me and Dupree, which is more or less a QOCWF, would have been atrocious, too, if it weren't for the presence of Owen Wilson, who keeps things fun enough to pass the time.
Wilson plays Randolph Dupree, a dreamer who' perpetually recuperating from the last time he fucked up. We first see our man in a budget propeller plane as he' landing in Hawaii to attend his friend Carl' wedding. He' late because he initially went to the wrong island-goofy Dupree blooper No. 1 out of 3,000.
After the wedding, Carl Peterson (Matt Dillon) and his wife Molly (Kate Hudson) are settling into their new lives as married people. Other than the fact that Carl works for a nasty land developer who also happens to be Molly' overbearing father (Michael Douglas), everything appears to be hunky dory. But one night while he' out with the guys, Carl discovers that Dupree has lost his job, home and company car. He was sleeping on a cot in the back of the bar until the regulars there voted to boot him out. Upon learning this-Dupree blooper No. 2-Carl invites Dupree to crash with him and Molly until he gets his shit back together.