Some movies feel effortless, like the crew and actors came on the set and magic made itself. You, Me and Dupree feels effortless – but more like no one made even bothered to try to make a decent movie. The film is a mishmash of half-baked jokes, sitcom scenarios and Owen Wilson attempting to float by on his charm.
I thought about walking out of Dupree at least three times. The film drags like RuPaul, mainly because someone decided that laughing too much might upset the audience. It isn’t just that Dupree’s jokes don’t work – there really aren’t that many of them. The basic plot has Matt Dillon, playing either You or Me, as a guy marrying the boss’ daughter (Kate Hudson as either Me or You, and often clad in next to nothing). His best friend is the party boy slacker free spirit Dupree, who loses his job for taking a week off to attend the wedding. Feeling guilty, You or Me allow Dupree to stay with him and his new wife. I assume hilarity was scheduled to ensue, but got caught up in traffic.
One of the most frustrating things about the film is how Dupree has no actual character. The guy often comes across as functionally retarded whenever it’s necessary for his wacky ways to get him into trouble/piss off You and Me. Then he’s suddenly a world class chef, or a hopeless romantic who writes poetry, or – for reasons that never become fully reasonable – an obsessive bicyclist. I don’t have a problem with someone having these traits, it’s just that the film waits until the second half to reveal them.
The reason it waits is that it gives us a crazy “reversal” – in the beginning Kate Hudson can’t stand having Dupree around and Matt Dillon is defending him/getting in trouble because of him. But in the second half Dupree nearly burns down the house, which is apparently the key to Kate Hudson’s heart (other key: being a junkie rock star). This begins what could have been an interesting storyline – it’s clichéd to have the friends turn against each other (only to make up at the end, duh), but here Dillon seems to be actually coming apart. The guy’s going completely fucking nuts, and suddenly I understood why they cast him. I mean, the You or Me character is an ex-frat type of guy who now works hard to get ahead – he’s supposed to be the clean cut yet identifiable character. To me Matt Dillon always gives off the vibe of the kind of guy who goes into a Boston bar at 3 in the afternoon and doesn’t leave until he’s bottled someone. When the film escalates to the point where Dillon assaults Wilson, things finally seemed to be picking up. It doesn’t last long, though – the movie goes on to create a madcap scenario where the two friends bond once more.
What’s really interesting about the movie is that Michael Douglas plays an evil land developer who happens to be Kate Hudson’s dad, and you can almost see where they trimmed away the edges of the usual evil land developer character so they could have the movie finish with a happy ending. Is the new development he has Matt Dillon working on environmentally unfriendly/unsafe/constructed on an Indian burial ground? No, but it really feels like it should be. All we end up with is a poorly motivated bad dad who is making his new son in law’s life a living hell only to suddenly switch gears at the end. The use of the character type, removed from its usual arc, makes this movie disorienting – you’re very used to the clichés that the film has been serving up, so when one of them doesn’t work right you notice. And it doesn’t even make logical sense – unless Daddy met his new son-in-law for the first time at the wedding (and they work together, so – unlikely), what kind of an asshole waits for the vows to be exchanged before he tries to run off his daughter’s boytoy? That’s not even taking into account the fact that the wedding is big and on Hawaii, and must have cost a fortune. So he’s an asshole who just pisses money.
I’ve been long wondering how long Owen Wilson’s laid back stoner/surfer persona could support him – the answer is up through Wedding Crashers. In this film he’s annoying and he’s not enough to support the proceedings. I assume that the film is going for the same chemistry that Wilson has with Ben Stiller, but he and Dillon don’t click in that same way – again, Dillon’s just too naturally menacing.
The only bright spot in the film is Seth Rogen, who just doesn’t get enough screentime. The funniest films of the last few years – much like the funniest films, period – are ensemble films, where a number of people get to be funny. You, Me and Dupree makes some feints in that direction, but the lesson it didn’t learn from The 40 Year Old Virgin was to give the supporting comedic players lots of room. More Rogen would have upped the comedy without a doubt, and maybe given the film a layer of depth that it currently fastidiously avoids.