Gus Van Sant tells the story of a young African American man named Jamal who confronts his talents while living on the streets of the Bronx. He accidentally runs into an old writer named Forrester who discovers his passion for writing. With help from his new mentor Jamal receives a scholarship to a private school.

In this loose adaptation of Shakespeare's "Henry IV," Mike Waters is a hustler afflicted with narcolepsy. Scott Favor is the rebellious son of a mayor. Together, the two travel from Portland, Oregon to Idaho and finally to the coast of Italy in a quest to find Mike's estranged mother. Along the way they turn tricks for money and drugs, eventually attracting the attention of a wealthy benefactor and sexual deviant.