The story of two hustlers turning tricks on the streets of Portland, Oregon seemed an unlikely starting point for arthouse director Gus Van Sant to finally achieve mainstream success. Certainly no one expected the film to take three times its budget at the box-office. The script was also exceptional among teen-angst projects for drawing on a classical work, Henry IV Part One, for its inspiration (one 'William Shakespeare' is given a co-writing credit). Scott (Reeves) is the scion of a wealthy family who, like Prince Hal, can give up his days of slumming and carousing when the appointed time comes. That choice isn't open to Mike (Phoenix), a narcoleptic drifter who is doomed, like Falstaff, to be rejected by his closest friend and left to his uncertain fate. While both actors were widely praised for their roles, it was Phoenix's haunting - and haunted - performance just two years before his death at age 23, that is perhaps the film's greatest legacy.