Garry Winogrand’s photographs constitute an unflinching yet empathetic portrait of Cold War–era America. Attuned to incongruous juxtapositions, unexpected beauty, and the fascinating variety of humankind, Winogrand made a fine art of street photography, capturing scores of images imbued with mystery and poetry. Sasha Waters Freyer’s poignant documentary foregrounds Winogrand’s photographs, combining them with 8mm home movies and recordings that allow his words and voice to resonate along with the images. Eminent curators, photographers, scholars, and friends address the personal and historical context of Winogrand’s works; their contradicting analyses and assessments provide the most powerful argument for the enduring relevance of the photographs.