We meet Carl (Matt Dillon) and Molly (Kate Hudson) the day before their paradise wedding, but then Carl has to go and pick up his best man and old school buddy Dupree (Owen Wilson), who had flown to the wrong Hawaiian island: “they all sound the same”.
Back home after the nuptials, Carl arrives at the pub for the regular guys night out and hears that Dupree has been fired from his job, lost his apartment and had his company car taken away. Dupree –never happier than when near a pool table and a bowl of pretzels – is quite happy to sleep behind the bar, but Carl insists that he comes to stay with him and Molly until he gets himself sorted out. Big mistake.
Molly is skeptical, especially when there are some very early disasters – a small fire, a blocked toilet and the humiliation of walking in on Dupree “romancing” her work colleague Wendy with a knob of butter – but Dupree’s got a big heart and means no harm. He’s an instant hit with the local kids as well – they love to hang out and go skateboarding with him.
Carl is not having such a good time though; having married the daughter of his boss Mr. Thompson (Michael Douglas) he has suddenly been given much more responsibility as is working longer hours. Underneath all that, he is sure that Mr. Thompson doesn’t really like him at all, especially when he suggests that Carl considers getting a vasectomy.
With the Honeymoon Period wearing off and Dupree’s hapless but good-hearted attempts to get on with his life stalled, Carl becomes convinced that Dupree has his eye on something else: Molly. Three’s become very much a crowd…
Wilson is responsible for plenty of funny moments in You, Me & Dupree, but writer Mike LeSieur has injected some effective drama and emotion into the story as well. Alongside his well-known improvising, Wilson also does something you don’t often see; he acts with his body too, using a number of walks and slouches to emphasize his character.
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