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.
At this point of the film, you can pretty much predict what Dupree' going to be doing. He clogs the toilet, walks in on the lovebirds groping each other, messes with their cable and gets caught masturbating. This section constitutes bloopers No. 3 to No. 33.
"At least he doesn't burn down the house," you're thinking, "because that would be trite as hell." We'd rather not spoil it, but okay, yes, he causes a fire while literally buttering-up a lady he' brought home.
For the first chunk of the film, it' basically a seesaw: over and over again, Molly is pissed about Dupree' actions, then Carl gives him another chance. By the second half, Carl begins getting mad too, which is problematic because Matt Dillon is incapable of acting angry.
When the subplot with Carl' job becomes the film' focus, the already sputtering storyline hits a brick wall. Because Carl is a poorly drawn, emotionally retarded character, he fails to capture our empathy, and because Matt Dillon is poorly cast in this role, we spend the final quarter of the film cringing.
Owen Wilson began his career by co-writing and starring in Bottle Rocket, in which he played a character named Dignan. Like Dupree, Dignan's a slacker pain in the ass to a more anal counterpart. But unlike Dupree, Dignan was one of the finest performances Wilson ever turned in. If nothing else, let's hope Dupree' blatant attempt and failure to imitate Bottle Rocket' success will convince Wilson to end his 5-year hiatus from screenwriting and that any slacker comedy worth doing is worth writing himself.