Portrait of Jason (1967), directed by Shirley Clarke, is a striking documentary that intimately portrays the life and personality of Jason Holliday, a Black gay performance artist. The film unfolds around Jason’s extended monologues, anecdotes, and personal confessions during a night in New York. With his unique humor, Jason candidly and poignantly shares his challenging life story, addressing issues of race, gender, class, and identity. The film is recognized not only as a portrait of Jason’s individual experience but also as an important work reflecting the social and cultural dynamics of 1960s America.