Bobby Long (John Travolta), a former professor turned full-time drunkard, and Lawson Pines (Gabriel Macht), Long's former teaching assistant, spend their days drinking and swapping literary quotations in a New Orleans house owned by a deceased lounge singer. When the singer's daughter, Pursy (Scarlett Johansson), shows up to reclaim her mother's property, Bobby and Lawson try to grift their way into keeping the home while attempting to convince the high-school dropout to pursue an education.