You, Me and Dupree

You, Me and Dupree (2006) is an American comedy you can watch online on iFILM, directed by brothers Anthony and Joe Russo. Newlyweds Carl and Molly have barely unpacked when Carl's best man Randy Dupree shows up at the door — jobless, homeless, and apparently unaware of what "temporary" means.

Owen Wilson plays Dupree as a force of cheerful, unself-conscious chaos: he sets a minor fire trying to fix the plumbing, turns the living room couch into a date venue, and somehow becomes the household favourite before Carl does. Matt Dillon and Kate Hudson play the couple unwinding at different speeds, which is where most of the comedy comes from. What starts as a gag about an overstaying houseguest quietly turns into something sharper — a look at how much space two people actually leave each other once the honeymoon is over. Watch You, Me and Dupree (2006) online on iFILM.