Ben Singer (Matthew Broderick) is a failed children's folksinger, a career proofreader, a less-than-extraordinary weekend dad, and perhaps the most negative man alive. Floundering in all aspects of his life, Ben's only comfort comes from regular chess games and friendly debates with his Senegalese roommate Ibou (Michael Kenneth Williams). When Ibou is struck ill, his sister Khadi (Sanaa Lathan) stays for an extended visit. Her influence helps Ben realize that cynicism may be all a matter of perspective.