Dupree (Owen Wilson) is the lovable slacker best man for Molly (Kate Hudson) and Carl Peterson (Matt Dillon)'s Hawaiian wedding. Carl is working for his property developer father-in-law Mr. Thompson (Michael Douglas) who keeps trying to emasculate him. Molly is a schoolteacher. Dupree becomes homeless and jobless. Carl takes him in for a few days which Molly reluctantly accepts. However, a few days don't last a few days.

Dupree is the house guest that overstays his welcome. He makes me want to kick him out and that's how I feel about the movie. It could still work with Owen Wilson as a likable goof but Matt Dillon is too intense of an actor. The chemistry is off. It would be better if Carl is played by a comedian or somebody with a lighter touch. It also makes Carl's later jealousy much harsher and darker. None of that is particularly funny.

This very much starts as a slacker type comedy with raucous male friends as Matt Dillon gets married and starts a new life as a newlywed married to Kate Hudson and he is working at his father in law's company (Michael Douglas.)

However Dillon takes in Dupree (Owen Wilson) when he goes through a rough patch and we cringe as Dupree turns his life upside down with his nasty habits even leading to his house being burnt down.

At work his father in law becomes overbearing even hinting that he does not want him to have children and wanting him to take his own surname. Now if Douglas's family name is so important to him why does he not want grandchildren?

No wonder Dillon is going out of control and his relationship with his wife suffering as a result. He seemingly has no one to turn to. Dupree his best friend seems to have better relationships with the kids in the neighbourhood as children are the only ones he can relate to.

The film has no idea what it wants to be. It is not a romantic comedy nor a comedy at all.

Maybe a dark comedy especially with Douglas overbearing on Dillon but this is punctured with the slapstick from Dupree and some of Dillon's friends such as Seth Rogen.

Dupree is hard to sympathise with even if you are a slacker although in the latter part he starts to inexplicably grow up. Also you can tell the film is not so good as you never believe in Dillon and Hudson as a couple.

I wasn't sure what to make of the movie after I watched the trailer. I knew it could be a great movie, but I also was afraid, that this was going to be incredible boring. After watching it, I feel somewhere in between!

Dupree is lovable on the one hand, but on the other hand you also hate his guts! Would you take as much, as Matt Dillon did? Probably not, but then this wouldn't be a feature movie then. A short film maybe. But the film has some genuine funny moments. Some involve Michael Douglas, who brings some hilarious moments with him, but is again another character, from whom Matt Dillons character suffers. So in the end, it's just comes down to the question, how much can you suspend your disbelieve and how much you're willing to overlook the mistakes that are made here and ... just laugh (now and then)?