This Forgotten Street Photographer Shot Some of Our Most Iconic Images

More importantly, Winogrand helped usher in an era of renegade artmaking with his documentary-style snapshots of bustling city streets and wild animals, pushing fine art photography out of the studio and into the real world. You may not have heard of him, but he’s likely the guy your favorite street photographer on Instagram is consciously or subconsciously emulating.

Winogrand himself was a larger-than-life figure armed with a gravelly Bronx accent and no-nonsense demeanor. He scraped by for most of his career, never enjoying huge financial success and dying young at just 56, leaving behind nearly 2,500 rolls of undeveloped film.

The new documentary Garry Winogrand: All Things Are Photographable not only examines his place in art history but also his sometimes chaotic personal life. Admirably, the film doesn’t pull any punches or attempt to lionize the photographer without also carefully weighing his more debatable artistic choices. These thoughtful critiques help the film achieve a rich, complex portrait of the artist. VICE spoke with director Sasha Waters Freyer about her new documentary, which received its theatrical debut at Film Forum in New York.

VICE: What first drew you to Garry Winogrand’s work?
Sasha Waters Freyer: He was still pretty widely taught when I studied photography as an undergraduate in the 90s. I was really interested in him mainly from a formal perspective… the way he put so much inside the frame before it was just total chaos and completely fell apart. And then, like a lot of people, he dropped off my radar because he sort of fell out of fashion. And then, in 2013, there was a new retrospective of his work that opened at the San Francisco Museum of Modern Art, and I remember reading an article and seeing those photos and being like, “Oh my God, Garry Winogrand! He's still amazing!” I hadn’t thought about him in 20 years.

You know, sometimes there are things that you're passionate about when you're 20, and when you look at them again as an adult, they don’t hold up. But when I went back, I was like, “No, this guy is still totally great.” And he famously had this big exuberant personality and was very complicated… I just kind of said, “Why isn't there a documentary about him?”

One thing I immediately noticed was how his photographs have this effortless quality to them.
His photographs look very easy, right? You look at that work and you're like, "I could take photographs like that." But you can't, you know? Like, go spend a month at a zoo making pictures. You will not make a picture as good as the couple standing in front of the wolf cage with the wolf walking up behind them. It's so hard to make that work, and he makes it look really easy.

I was waiting for the part in the documentary where he starts a job at some big photo journal, steals a extra few rolls out of the newsroom at night, and starts shooting his own work on the side. But that’s not how it happened, right? He just dipped on his job to become a full-time artist.
The idea that you were going to be an artist and make money was absurd. I mean, that's why his second wife left him. She was just like, "This is fucking crazy. This guy doesn't pay his rent. He doesn't pay his bills. He doesn’t pay taxes. He barely pays his child support." He literally was just doing what he needed to do to get by in order to keep making photographs.

But the art market is completely transformed now, and that didn't really happen until the 80s. Nowadays, I think there's so much pressure on young artists to think about the marketplace in a way that it’s hard to imagine when it didn't exist.

But the financial struggle stayed with him his whole life.
Totally. And he really fell out of fashion. He did this book called Women Are Beautiful in the mid 70s that really, really hurt his reputation. I mean, just in terms of the editing… it's kind of problematic. I understand why he took certain photos, and I appreciate it as a document, but I think it’s kind of an eye roll.

The title doesn’t help much.
People were like, "Oh, this is totally objectifying women. This is not how we want to be seen. This is not why we're out on the street in our bikini tops. We're out for our own self-expression and empowerment, and not just sort of as decoration." The irony, of course, was that he thought that book was going to be a big hit.

Someone has a great quote in your film about how the ways in which artists capture the world can go in and out of style.
Oh, that was Matthew Weiner, the creator of Mad Men. I think he discovered Winogrand when he was already making the show. He was a really huge fan, because he thought so much about that period, and that transformation of women, and how to represent it visually.

And I do think that, in defense of Women Are Beautiful, there are a lot of ways in which it is a celebration of women. It is a really important document of this period when women are entering the workforce and making themselves visible in a way that was completely new in American society. If you look at pictures of women from, say, New York in the late 50s, the way they’re dressed, the way they carry themselves, they way they engage with the camera… it’s completely transformed by 1972. Everything about the way women are self-presenting in public is transformed so radically in the 1960s.

Did your view of that particular book change after realizing where Winogrand was, personally, at that point in his life? Wasn’t he on marriage number three?
I became much more sympathetic towards him. I think he was just a complicated person who was trying to live in the world, and that's what we're all trying to do.

I got a very specifically titled jury award at South by Southwest. My award was for “Best Feminist Reconsideration of a Male Artist.” I was like, “Oh, this jury completely fucking got this film.” I didn’t want the film to just be worshipping him.

I think the thing that makes it a very feminist film is that we don’t often think of a male artist and their relationship to marriage and children and family and how it impacts their artistic output. But it’s a question that’s constantly asked of female artists. And for male artists, the stupid cliché is, “Oh, he’s a jerk, but it’s OK because we have this great novel or painting.” And with Winogrand… the ways in which he struggled to find a balance between being a good husband, being a good father, and also being a good artist… it was certainly painful at times.

You walked a fine line between highlighting his canonical work and influence but also investigating areas that were a little rougher.
About 22 minutes in, you hear him talking to his friend Jay Maisel. He talks about how, when he’s trying to get with women, he tries to convince them. But if he can’t convince them, he convinces them with the other hand. He likes to grab. And the “grab” verb, in particular, is problematic.

There are definitely people who shut down and are like, "Fuck this guy. I don't want to hear anything about him." But I also think that if you can get past that moment in the film, which is pretty early on, I think that young people actually really connect to him and appreciate him, because he speaks to the idea of learning through doing the work.

But what do you say to somebody who says, "He objectified women, so fuck him?”
Personally, I'm not interested in a personality litmus test in regards to the artists I'm interested in. I do think that it probably helps that I'm a female filmmaker. I think there’s potential for redemption baked in by gender, in a very straightforward, normative way.

I guess I would say… he objectified men. He objectified the world. I don't think he was making objects of humans, but I think he felt outside of a certain kind of human community, and he was trying to figure out a way to fit in. If you look at his series of men in particular, he's constantly photographing businessmen in New York. He was a first-generation Jewish American, who was really first-generation assimilated, and actually, not assimilated, right? I mean, even in New York, as a Jew from the Bronx, he worked in advertising agencies in the early 50s. He couldn't have done that five years earlier. They wouldn't have hired Jews.

So his mainstreamness is really complicated by his immigrant Jewish background, even if he presents "passively” as a white man, he's totally an outsider. He's trying to figure out how to live in the world.

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Greg Eggebeen is on Twitter.