A couple of days before cashing in on a free Caribbean cruise for two, dorky Brooklyn hipster Max (Sean Bones) gets dumped by his girlfriend (Norah Jones, in a tiny cameo)—perhaps because he has no personality and his mouth hangs open like half an idiot—but takes the trip alone anyway. Strutting around the ship's senior citizens in a daze, he barely talks to anyone, and eventually docks in Jamaica, where he naïvely gets in a car with the first stranger who smokes weed. Through a series of increasingly dumb-ass decisions, Max loses his money, passport, clothes, and boat ride back home. Meanwhile, TVs and newspapers in the background hint that Obama is about to win the U.S. Presidency, but our superficial hero can't be bothered to notice in filmmakers Ben Chace and Sam Fleischner's glorified vacation video. The two wrote this slight, handheld-shot drama around a free cruise that Ben won, then upped their indie cred with supporting players from Yeasayer, MGMT, Suckers, and the Congos. If Max had been knifed to death for his oblivious behavior (the threat does exist), the film might've been a critique of ugly Americans embarrassing themselves in front of indigenous folks, but methinks we're meant to actually feel sorry for this privileged twerp in neon sunglasses.