Matt Dillon has gotten some great laughs in movies like There’s Something About Mary, but he’s far better known for serious work in films like Crash. He may not get an Oscar nomination for You, Me and Dupree, but it’s potentially harder work than making a racist seem sympathetic. Dillon plays the best friend of a moocher who invites chaos into his new marriage by letting Dupree stay over.

“I like to do comedy, but I’ll be perfectly honest, I prefer to do drama and more character-driven-based stuff, generally,” Dillon said. “I found this is one of the more difficult roles that I’ve had to play because the character’s the straight guy, he’s very reactive. And I think where the comedy is with that type of character isn’t like a look or a reaction. God knows, I’ve had plenty of those in this film. So I thought for me, it was really important at the end that Carl stands up for himself, and I think that was important for a satisfying denouement. Also, he had a hand in all this chaos. In fact, he was the one who made the decision to invite Dupree into his home, so he kind of deserves, to a certain extent, whatever he gets. But I think Carl is the character that most people will identify with. I certainly have had multiple Dupree’s in my life over the years.”

As Dupree, Owen Wilson is a natural at those lovable troublemakers. Despite their different outcomes, his style of improvisation helped Dillon get into the comedic mindset. “I was pleasantly surprised to find that Owen liked to work spontaneously. We did a fair amount of adlibbing, and I found that very refreshing, because I like to work that way. And in comedy, that can be gold, because you never know what’s going to work. There’s a kind of magic that can happen when you’re spontaneous, it keeps you connected, and so I liked the way Owen works. It’s very natural.”

That sort of spontaneous flow is what Dillon has devoted much of his craft to achieving. “I had acting teachers, and one of the things that was encouraged was to keep it fresh, to be spontaneous. That’s the magic of film often. Or those mistakes, I’ve noticed at times in my career, it’s like the moments in the scenes I’ve done where I was like, ‘That was just awful,’ turned out to be some of my best work. And it’s interesting because something authentic has happened. If you say ‘I forgot my line’ or ‘I didn’t know what I was doing at that moment’ or ‘I lost focus,’ in fact there’s something very organic that’s happened that’s real, that’s happening in that moment. So I think what I’ve learned is to accept is those are the magic moments and that happens when you’re willing to be spontaneous and fresh.”

In You, Me and Dupree, Dillon found those moments in little incidents that were not originally intended for comedic effect. “Like when I’m getting out of the car and grabbing my coat and all these things have to match and I’m frustrated in this scene and I realize I forgot that thing and so we have to cut. In that moment, I think, ‘Oh, damn.’ And then I just use that and I just go with it. It’s that sort of thing of keeping it real. If you feel like something went wrong, you just keep doing it. That’s sometimes where the best moments are.”

Since he admitted to having Duprees in his life, the natural question would be whether he or brother Kevin Dillon is a Dupree. Kevin’s character on Entourage seems like a Dupree, living off his more successful brother, which leads to speculations on the real Dillon clan.

“In a different way; I had that with all my brothers at one point and friends. I’ve had a number of Dupree’s in my life. Friendship is important to me, so you end up putting up with some things because you like these guys despite their shortcomings. They’re your friends. And then your brothers, obviously, blood is thicker than water. But it’s hard to know because Dupree is unaware of the fact that he’s this crazy maker, so I’m sure I’ve been that to someone but I was probably unaware of it. And I’d say if I were a houseguest, probably, I have a tendency to like to play my music loud and that might be something that bothers people. My driving, I’ve been accused of not being the best, most safest driver.”

With Entourage a success, full of inside Hollywood references, it seems like the perfect opportunity to get the Dillon brothers together. But since Kevin already plays a character, it’s hard to figure out whether Matt should be himself or another character.

“I think the hard thing about that show is he’s got a brother already, so I don’t know if that would work out. But we’ve talked and I have said I’d love to direct one. He’d love that. But we’ve talked about it over the years, we’ve just never found a script.”

Dillon has another film coming out this summer, Factotum, and hopes to get back to writing his own scripts. He’s also entertaining several offers. “I don’t think I’ve ever been at a better time, career wise. And I think it was fun to do this comedy with these people, a bigger studio comedy, and it’s different and it’s a nice contrast to what I did with that. I’m excited about the future. I really feel like I couldn’t be in a better situation from where I’m at right now.”

And it really was an honor just to be nominated. “That was a great experience. That was a lot of fun. Obviously it doesn’t happen every time, and you can see that. There were a lot of terrific films made last year that didn’t get recognized and performances, so it’s really an honor to get recognized like that. That was a lot of fun, I really enjoyed it. A lot of people were upset that we won and Brokeback didn’t. What do they bother getting upset at? The fact is all those films that got nominated won, and at the end of the day, it’s a great honor, but what’s important, at the end of the day, I don’t say that film is my favorite film because it won the Oscar in 1956. I judge films on the way they’re made; I was very proud to be part of that film. To me, I just show up to everything, and the weightiness of that character lent itself to the work I like to do.”

You, Me and Dupree opens Friday.

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