Harry and Tonto (dir. Paul Mazursky, 1974) uses the American road movie, a signature genre of late 1960s and early 1970s film, to address the experience of an older man who, exiled from his home, travels through America, coming in contact with the nation’s counterculture and working-class culture, in the process reassessing himself and his place in American society. Though the film was critically lauded in its day, few Shakespeare film scholars afterwards have explored its many parallels with King Lear, even though passages from the play are explicit points of reference in multiple scenes and there are myriad echoes of Lear in characterization and narrative. This chapter examines how and why writer-director Paul Mazursky brought Shakespeare’s King Lear and the American road movie of the early 1970s into productive dialogue with one another. Lear provides a means for broadening the range of the road movie beyond youth culture, allowing for re-examination of relations between generations and suggesting the congruence between Lear’s ‘unaccommodated man’ and those outside the American cultural mainstream. At the same time, the road movie provides King Lear a means to be accommodated to a specifically American sensibility.