Randall Dupree enjoys life. In fact, he freely admits that happiness is his number one goal and he won't let things like not having a job or a place to live stand in the way. This 30-something free spirit is overjoyed to be best man at the wedding of his best friend since childhood, Carl; but that relationship is not the only one put to the test when, right after the honeymoon, Carl tells his bride Molly that they have an unexpected house guest.
To Molly, it seems like Dupree is moving in for a more extended stay, and it doesn't help her mood when she accidentally discovers his habit of sleeping 'au naturel.'
Owen Wilson turns on all his boyish charm in the role of Dupree, the guest who will not leave.
"Kind of like Dupree, I think I definitely try to avoid being jaded or cynical. I try to have enthusiasm. Dupree carries that much further than I do, but I think that's a very good quality," he says.
Wilson says the film's plot mirrors experiences he has had with his brothers Luke and Andrew and familiar to many, if not most, young people newly on their own.
"There have probably been some times that I have been like Dupree. I know that my older brother says that Luke and I wrecked his first marriage because we were always staying at his house. We had a ladder set up so we could go into the second-story window. One time Andrew had locked me out and I needed to get some of my clothes and I fell through the ceiling. That made its way into Dupree. So, yes, I think I've experienced that; but I've also been on the other end. I had Woody Harrelson staying with me and I'd say 'well, I'm on my way to a meeting, Woody. I'll talk to you later on.' He answered 'wait, are you going in your car? What am I going to do?' ...So it felt that Woody was a little like Dupree," he says.
"Oh yes, I've had multiple 'Duprees' in my life over the years: friends of yours who sort of get into your life and they are more entanglements than they are relationships," says Matt Dillon, who co-stars as new husband and put-upon best friend Carl. "Even though Dupree is like his old friend, as soon as he comes on ...he doesn't do it deliberately, he's guileless [and] he means well ...everything he does is disastrous for Carl, so Carl finds himself often having to clean up for Dupree. I have had friendships like that. I can think of a number of things in this film that really mirror things in my own life in some way," he says.
"It's funny, Molly, my character in the movie, as patient as she is, I'm still a little bit more patient," says Kate Hudson, who plays newlywed Molly and says she knows the Dupree phenomenon well in her off-screen life, with unexpected and extended stays by, among others, colleagues of her rock star husban, Black Crowes lead singer Chris Robinson. "I actually kind of enjoy it. I enjoy a lively house. I enjoy weird characters. I had one who was crashing at our house for over a year - my best girlfriend - so, what are you going to do?"
However, Hudson believes that the situation in the film - the husband's best friend moving in - is more typical of what really happens.
"I think it is a guys' story. I think it's a story about a guy who loses his best friend to his new best friend, who is his wife. As much we're all on screen together, the movie is about the passage of marriage and what it means for people, especially for Dupree, when they lose their friend. We're getting a little too serious; it is just a comedy, but there is this sense that in a guy's world, sometimes it is just all about the guys ...and that's okay," she says.
You, Me and Dupree also features Michael Douglas as the doting father of the bride (and the groom's boss). There's also a cameo by Dupree's inspiration, bicycle champion Lance Armstrong. The comedy is co-directed by filmmaking brothers Joe and Anthony Russo.