A half-century after its release, Midnight Cowboy remains one of the most original and groundbreaking movies of the modern era. With beguiling performances from Jon Voight and Dustin Hoffman as two loners who join forces out of desperation, blacklist survivor Waldo Salt's brilliant screenplay, and John Schlesinger's fearless direction, the 1969 film became the only X-rated film to ever win the Academy Award for Best Picture. Its vivid and compassionate depiction of a more realistic, unsanitized New York City and its inhabitants paved the way for a generation's worth of gritty movies with complex characters and adult themes. But this is not a documentary about the making of Midnight Cowboy: it is about the deeply gifted and flawed people behind a dark and difficult masterpiece; New York City in a troubled time of cultural ferment; and the era that made a movie and the movie that made an era. Featuring extensive archival material and compelling new interviews, director Nancy Buirski illuminates how one film captured the essence of a time and a place, reflecting a rapidly changing society with striking clarity.