Ben Singer (Matthew Broderick) is a failed childrens folk singer, 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 on game theory with his Senegalese roommate Ibou (Michael Kenneth Williams). When Ibou is suddenly struck ill, Ben's pessimistic worldview seems unequivocally confirmed. It takes an extended visit from Ibou's sister Khadi (Sanaa Lathan) for Ben to realize that cynicism may be all a matter of perspective.
