This documentary makes the top of the list because, as those who have seen it will attest, it's perhaps the best film you could never watch more than once. Released in 2008, this doc from director Kurt Kuenne tells the story of Kuenne's longtime friend and supporter, Andrew Bagby. Andrew meets and falls in love with Shirley, a woman 13 years his senior, and the pair eventually have a son together named Zachary before Shirley begins to reveal herself as mentally unstable, to say the least. To say much more would be to rob you of the visceral, engrossing experience as relayed through Kuenne's unique editing style. The filmmaker's fast-talking voice overs are enervating as he unleashes a story that will break your heart into a thousand pieces.