A bittersweet comedy about families, friends and a frivolous fight against corporate institutions, Matthew Broderick plays Ben Singer, a failed children's folk singer, a newly unemployed proofreader and an every-other-weekend dad to his young daughter (Jodelle Ferland), who prefers pretty much anything to listening to her dad's pessimistic ramblings. Struggling in all aspects of his life, Ben's only comforts come from smoking marijuana alone and regular chess games with his smart and opinionated Senegalese roommate Ibou (Michael Kenneth Williams). When Ibou is suddenly struck ill and an insensitive municipal employee exacerbates the emergency situation, Ben pours his energy into a lawsuit against the city for depraved indifference. Ben's life begins to turn around with the arrival of Ibou's beautiful and sexy sister Khadi (Sanaa Lathan) from Senegal, who moves into Ibou's room in Ben's apartment. As Ben suspects that it is his own cynicism corroding the beauty around him, he realizes that it's all a matter of perspective.