Ben Singer (Matthew Broderick) is a failed children's folk singer, a career proofreader, a compulsive marijuana smoker, and a less-than-extraordinary weekend dad. He's also 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, and an insensitive municipal employee exacerbates the emergency situation, Ben's pessimistic worldview seems unequivocally confirmed. His only recourse is to pour his energies into a frivolous lawsuit against the city for depraved indifference. But Ben soon finds that cynicism may be all a matter of perspective.