John Schlesinger’s 1969 film Midnight Cowboy won the Academy Awards for Best Picture and Best Director, as well as Best Adapted Screenplay for writer Waldo Salt, for its depiction of the fraught and tender relationship between two men striving to exist in 1960s New York. Inspired by Glenn Frankel’s 2021 book Shooting Midnight Cowboy: Art, Sex, Loneliness, Liberation, and the Making of a Dark Classic, Nancy Buirski’s documentary explores this groundbreaking movie, but her attention is trained on the people who made it and the times in which it was made. The vibrant soundtrack punctuates kaleidoscopic visuals that include excerpts from Midnight Cowboy and stunning archival imagery of New York. Interviews with actors Jon Voight and Bob Balaban, alongside critics like Lucy Sante, not only convey the film’s personal significance but also its larger political context—the Vietnam War and Black, gay, and women’s liberation movements. Buirski creates a portrait of Midnight Cowboy that expands far beyond the making of a movie to consider the ways an X-rated picture about the experiences of a male sex worker came to embody a cultural moment.