It's difficult to talk about Street Photography without talking about Garry Winogrand. Winogrand would typically carry two Leica M4's with 28mm lens attached, loaded with Tri-X film and shoot copiously. He died in 1984 at age 56, leaving behind 2500 rolls of unprocessed film. Read the excellent essay by Frank Van Riper and another by Mason Resnick called Coffee and Workprints: A Workshop with Garry Winogrand.
One of my favorite images from Winogrand is below, from the book, Garry Winogrand: The Animals. The Getty museum has this to say about this photo.
Garry Winogrand confronted tough issues like racism with a sense of humor, as he did here by photographing this black man and white woman holding apes. The chimpanzees are dressed like children and resemble the human child standing behind the couple. The photographer's close vantage point, the crowd, the dramatic winter light-all add a sense of spectacle. Winogrand was not simply reacting to a strange moment, but probably also to racial tensions sweeping the country at the height of the Civil Rights movement. The year this picture was made, black actors won Academy Awards, and the U.S. Supreme Court overturned state laws banning interracial marriage. It is not clear whether this man and woman were actually a couple, but Winogrand must have known that their togetherness was as unsettling to some people as their circumstances were comical.
Garry Winogrand, 1967. Central Park Zoo
Garry Winogrand, 1952. Coney Island, NY
YouTube Video of Winogrand:
Interview Part 1
Interview Part 2
Out of Print Winogrand book, Winogrand 1964