This photo essay, part of our collaboration with Magnum Photos, documents Alex Webb’s exploration of Chicago and the Loop. Inspired in part by one of his early influences, Ray Metzker’s “My Camera and I in the Loop,” he explores the streets of the US’s “Second City.” Though unlike the street photographers of the so-called Chicago School (Callahan, Metzger, Sturr, Sterling), Alex Webb has chosen to photograph the city’s multitudinous character in color. Having spent most of his 30 year long career shooting outside of the US, Alex Webb turns his lens to his home nation during this very important election year. We had the chance to pose some questions about his images and the city that inspired them.

Q: What was your goal with the photograph featuring an Obama t-shirt where the wearer’s face is in the shadows aside from the glaring lens of his sunglasses? It’s a very striking photograph that reminds me of a graphic novel with the sunglasses.

A: I did not have a goal in mind. In fact, I do not have goals in mind when I photograph. I respond to what I see before me. The creation of the image happens in a split second, before I am fully rationally conscious of what it is that I am photographing. The act is intuitive, instinctive and non-rational.

Q: I love the photograph of the girl on the bicycle — her colorful attire and bike pop out with how the light is cast and shadows in the rest of the photograph. When you mention cinematic close-ups, this seems to illustrate that. How did you approach capturing this cinematic feel with your street photography?

A: At certain days in the year a crisp, clear light pervades Chicago, enveloping the Loop in dramatic criss-crossing shafts of light. Capturing this sense of the Loop is no different than other street photography. It involves patience, anticipation, luck and persistence because, as we all know, the special images do not come easily; 99% of street photography, if not more, is about failure. It’s a bit like gambling — you try to get the odds in your favor, you work when the light is interesting, when there are intriguing things going on in the street and you keep hoping, against all odds, that something will work.

Q: The photograph featuring a painting of a man in a button down shirt with the passerby in the same blue button down and a statue of a man in a suit against a white marble backdrop is great. What message did you want to convey with this photograph? You mention cultural reflections and this seems to point out a corporate culture very different from the contrasts found near the Loop.

A: As I suggest above, I am not trying to convey messages. I take photographs to affirm reality, not explain reality and that reality often has a high level of ambiguity to it, which is subject to interpretation. So what one viewer discovers in a given image may be very different from what another viewer discovers. This particular photograph seems to suggest to you something about corporate culture, but another viewer might simply be amused by the similarity of be-suited figures and another viewer might find something else. I believe in photographs that have a level of ambiguity, images that work on suggestion, that ask questions rather than provide answers.

Q: From the Loop to street festivals — the rhythm seems to slow in the photographs of the festivals, but it also seems like you’re pointing out something else about Chicago. By taking a closer look into pockets of the cultural diversity found juxtaposed in the Loop, what were you hoping to capture?

A: I’m intrigued by the ethnic variety of Chicago, the simultaneous coexistence of many different cultures in what seems like a quintessentially American city. But then this poses the question of just what is quintessentially American these days. For the American city is an ever-changing entity. That’s part of what was exciting to me about photographing Chicago.

Q: Why did you choose to shoot this series in color?

A: Since 1979 I have worked predominantly in color. While I was initially inspired to work in color by my experiences in the tropics, I now respond to color everywhere. For me, right now, black and white just isn’t an option. I see in color and I feel in color, so I have to work in color. Also, working in color allows me to pay homage to some of my early photographic influences (one of the first series of photographs I remember seeing as a teenager was Ray Metzker’s “My Camera and I in the Loop” in an issue of Aperture magazine), who photographed Chicago in black and white.

Q: You posed the question, “Could a series of photographs from these urban streets begin to suggest a kind of state of the union for the U.S. today?” Is it a coincidence or purposefully chosen that you selected Obama’s hometown and campaign headquarters for this project?

A: There were a multitude of reasons why I chose Chicago, but one of them was that it is Obama’s hometown.

Q: There is one photo you took of a caballero on a white horse, which appears to be in stark contrast to what looks like a field growing around some old train tracks and the concrete wall behind him. Can you tell us more about what’s happening in this seemingly contradictory scene?

A: This picture was taken at a Mexican Independence Day celebration. I loved the notion of this most Mexican of celebrations taking place in this drab, run-down area of a North American city.

Q: I have often been told that Chicago is almost a hybrid of New York City and Boston. Do you agree and what do you think makes Chicago unique?

A: I’m not sure I agree that Chicago seems like a hybrid of Boston and New York. It is Midwestern, whereas the other two cities are distinctly Eastern. What I find particularly unique about Chicago is its architectural muscularity. Chicago’s particular ethnic mix is a key to the city’s uniqueness: a large Polish and Eastern European population, a historically powerful African-American community and one of the largest Mexican communities in the United States.

Q: What is your next big project?

A: Over the past 30 years, I’ve photographed extensively outside the United States. I want to see what happens if I return to photographing more in my own country. I have been making some trips around the US, sometimes accompanied by my wife and creative partner, the photographer Rebecca Norris Webb, with whom I created the book on Cuba, “Violet Isle: A Duet of Photographs from Cuba.” Though it is at this point very much in a state of infancy, we are exploring the notion of creating another joint project.

-Leica Internet Team

You can see more of Alex’s work in his Magnum Photos portfolio and on his website,