Personally I'd rank the recently departed Helen Levitt above the others; her photos simply crackle with life. They look like effortless poetry, and demonstrate genuine respect for her subjects, particularly children. I must confess that I've never 'gotten' Gary Winogrand, despite repeated study of his photos and reading several long interviews in which he explained his work and what he was trying to do. His photos seem to lack any shred of sympathy for his subjects. Robert Frank likewise is no doubt brilliant and incisive, but his work is incredibly sarcastic. Lampooning late 1950s Americans? Like clubbing baby seals. I'm with you on Elliott Erwitt, though. He draws humor from street photos without showing contempt for people.
I'm a Helen Levitt fan too. She's one of my favorites. I have two of her books in my library and go through both fairly often. I agree with you about the quality of her photographs. I especially admire the one of the three kids in masks on the front stoop.
But the reason I listed the three phtographers I did is because, first, Cartier-Bresson practically defined 20th century street photography. He didn't invent it. If anyone did that it was Atget, lugging around a huge stand camera and plates, though Andre Kertesz has a claim for the "inventor" title.
But Henri was a formalist, and careful composition was one of his main strengths. Robert Frank stepped out of that mold and showed that you could put power into pictures that aren't as carefully composed as Henri's, and that sometimes careful composition can detract. I don't agree at all that Robert shows no sympathy for his subjects. I'd say just the reverse. I think he shows deep sympathy for them. Again, you haven't given any information about yourself in your profile, so I don't have any idea how old you are, but I turned 79 last month and I was in my middle and late 20s when Frank did his tour de force. I see those pictures as anything but sarcastic. What he did was tell the truth about that period. I remember how upset Popular Photography Magazine was with The Americans
, and it took me a fairly long time to understand what I was seeing when I'd look at the pictures in that book. But they grow on you as the truth begins to seep through.
Garry Winogrand is another guy whose work takes time to understand. Besides that, a lot of Garry's stuff that gets printed isn't all that good. It appears he lost it in his later years. But I think Garry is the guy who finally eliminated any residual doubt in the fine art world that photography is its own kind of art and that you can't judge photographs on the basis of what you've learned about painting.
And so, what I was talking about is the lessons you can learn from these three people, each of whom broke away from a tradition set by his predecessor. As far as my favorites are concerned, Elliott Erwitt tops my list because of his sense of humor, but also because of some of the singularly un-humorous shots he made. The picture of Jackie Kennedy at her husband's funeral, with Bobby in the far right of the frame comes to mind. But Walker Evans runs a close second and was my absolute favorite for a long time. Helen Levitt's right up there in the top group too. I can also add Steve McCurry, Robert Doisneau, Manuel Alvarez Bravo, Brassai, Gene Smith, etc., etc, etc...