Compulsive, obsessive, driven—none of these adjectives adequately describes Garry Winogrand, a giant among mid-20th-century photographers, whose lifetime output of images numbers in the hundreds of thousands, and whose shots of New York in the 1960s defined a city and an era. Inseparable from his Leica 35-millimeter camera, Winogrand was always looking for the moment that both caught the essence of random human encounters and commented on the culture at large. Although he died in 1984, he seems very much alive in Sasha Waters Freyer’s richly detailed documentary, where she adroitly employs his taped conversations with fellow photographer Jay Maisel to convey Winogrand’s outspoken, energetic, ultramasculine persona. Talking heads acknowledging Winogrand’s extensive influence include Mad Men creator Matthew Weiner and novelist and cultural critic Geoff Dyer, author of The Street Philosophy of Garry Winogrand, a parallel meditation on an artist ripe for reappraisal.