You, Me, and Dupree (2006)

It isn't like Matt Dillon, Kate Hudson and Owen Wilson possess wholly unimpressive resumes. Matt Dillon has an Oscar nomination. Owen Wilson has all of that cool Wes Anderson cred. And for people who don't understand that Cameron Crowe is a total hack who hasn't made a good movie since 1989, Kate Hudson represents all of the naïve wonderment of the Girl Who Doesn't Actually Exist character in Almost Famous.

But the stars of You Me and Dupree were also the stars of One Night at McCool's, The Big Bounce and Raising Helen, and it was the unfunniest parts of them who showed up to make the worst kind of comedy imaginable: one that revels in sheer human ugliness. Owen Wilson's Dupree crashes a brand-new marriage and immediately engages in behavior ranging from masturbating into a sock to burning his best friend's house down. Were it not for Mike Myers in The Cat in the Hat, Dupree would be considered the least welcome houseguest in film history. It would be funny if it weren't so desperately, tragically cruel.