The film opens in Hawaii, at the marriage of Carl Peterson (Matt Dillon) and Molly Thompson (Kate Hudson). Dupree is Carl’s lifelong friend and best man, despite being something of a screw up (he somehow wound up on the wrong island). The relationship is strangely co-dependant; it seems to thrive on Carl’s willingness to excuse Dupree’s weirdly impulsive behavior and general incompetence, and Dupree’s absolute admiration for all things Carl, which he dubs his Carl-ness. That seems to be a big part of Dupree’s philosophy- identifying a person’s essential nature, and then labeling it as that person’s name with “–ness” at the end.
As a friendship this arrangement appears to work out for the two of them. However, circumstances begin to change back on the mainland, when Dupree is faced with the simultaneous loss of his house, car, and job. Carl takes pity on him and invites him to stay over until he can get back on his feet. “It’ll be just a few days,” Carl explains to Molly. “Yeah right,” replies the audience.
Sure enough, days stretch into weeks, and then months, all the while Dupree’s irritating quirks begin to surface. For example, it’s only at about the halfway point when a mid-coital Dupree burns down Carl and Molly’s living room. And, while he does endeavor to find a new job, his efforts are lackluster at best. He tells one potential employer that he’s not really “task-oriented,” and repeatedly inquires about the company’s observance of obscure holidays.
On the other hand, Dupree becomes transfixed by trivial elements of his everyday life: skateboarding with the neighborhood kids, cycling, cooking for Carl and Molly, and so on… He pursues these goals with dogged determination. Often times I found myself playing Dupree’s guidance counselor; he obviously relates well to kids, why doesn’t someone suggest he work at a youth center? He’s apparently a very good cook, where’s his application for next year’s Top Chef? By the end of the film, when Dupree has cobbled his slacker ethos into a pop-psychology best seller, I mostly felt sad for him- it seems as though in his quest to help others, no one really tried to do the same for him. Where’s the Dupree-ness?
Other aspects of the film suffer from a similar lack of thought- in one case, Dupree is set up with a girl named Mandy who he pines for throughout the film, but is never actually seen on screen. It’s a scenario that cries out for some kind of payoff that the film never supplies. Another odd twist that never quite gets resolved is Carl’s relationship with Molly’s overbearing father (Michael Douglas). Mr. Thompson also happens to be Carl’s boss, and for much of the film, he is attempting (sometimes literally) to emasculate Carl.
Although the film’s resolution revolves around their reconciliation, somehow it doesn’t ring true. Part of the problem is that Matt Dillon doesn’t really play intimidation well; Carl would’ve been better off as a Jon Favreau in “Swingers” type guy. I would’ve rather seen someone who could be pushed around a little and freak out, but still be a likeable character, whereas Dillon never really seems to cede control in his scenes with Douglas.
Ultimately though, I have to wonder why I’m putting so much effort into what is essentially a disposable summer comedy. I think it’s because on a certain level, Dupree works as a character. In the end, the audience wants him to succeed and do well. Unfortunately for me, that meant wanting to see him in a better film than this one.
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