15Sideways (2004)

The story of two friends on a road trip through wine country is also an examination of the male ego in crisis. Miles is a broken-hearted unpublished novelist and wine connoisseur, Jack is a washed-up actor, living off the fumes of a career in daytime soaps. “Because we liked the novel so much, it was a struggle to keep the screenplay as short as possible,” Alexander Payne told Variety. Miles and Jack’s shenanigans—mostly Jack’s—crescendo in a decidedly offbeat act of male bondage. The 2005 Oscar- and Writers Guild Award-winning Adapted Screenplay comes to pack an emotional punch because the characters, and the friendship, are so believable.