Ben Singer (Matthew Broderick) is a deeply sarcastic man and an unsuccessful children’s folk singer. Ben's sole pleasure in life is obtained from smoking marijuana and playing chess games with his Senegalese cohabitant, Ibou (Michael K. Williams). When Ibou unexpectedly gets ill and an insensible municipal employee makes worse the crisis, Ben's pessimistic views become explicitly confirmed. He tries to file a lawsuit against the city for wanton apathy. But, when Ibou's beautiful and sexy sister Khadi (Sanaa Lathan) moves into their apartment, Ben's life begins to turn around, and he discovers that sarcasm may be nothing but a point of view.