Life in the city is absurd. We’re all crammed together in apartment blocks and buildings like so many lab rats. We run into each other on subways, spy on neighbors through windows, deal with the discomfort of being so close together. But then there’s the positive side of all that density: creative culture, great food, a never-ending parade of things to see. This is where the pseudonymous Chicago street artist Don’t Fret loves to dwell. His work—whether murals of people in their underwear, businessmen waiting at bus stops, or incisive one-liners on posters—is both bitingly funny and poignant. In preparation for the opening of Complex and FIAT’s My Design City Gallery on July 18—where Don’t Fret will be showing his work—I talked to him about his sources of inspiration and where his love for the ridiculousness of cities comes from.

Why do you work across so many different formats? You’re not just doing wheat pastes or murals, but creating indoor projects, installations, and drawings on paper.
I think it’s just about context. When I started I was only making work for the street, and I didn’t really think about doing a gallery show or even making work that was for sale. When I started to want to do shows and make work for galleries, I knew I couldn’t approach it the way I do when I’m making work for the street. But working in a gallery space (or more recently I did a show in a 75-year-old hardware store that was set for demolition) for me is about changing the space and taking the energy from the street and molding it into something different.

Image via Don't Fret

Your work often makes me laugh out loud, with its lightly absurd characters and satirical statements. What’s your sense of humor like, and how does that factor into your work?
I think, at certain points of my life, I have been kind of a glass half empty guy. So I like that I’ve found humor as a kind of tool for dealing with the “dark times.” I think humor might be our most important sense, and I’ve found with some of the more critical or social commentary aspects of my work that you can use humor as a way to hold peoples hands and engage them with ideas that might otherwise make them uncomfortable.

Your work really resonates with city dwellers who are familiar with the voyeurism and surrealism of urban space. Are you hoping to reach that crowd?
I grew up and currently live in a big city (Chicago), and I think some of the text work is just reactionary to some of the absurdities of living in a big city. I’m interested in absurdity and kind of taking a notion and skewing it a different way. “Live by the sword, die by your peanut allergy.”

How do cities act as a source of inspiration for you?
Living in a city means living with other people, and at times I think it means “dealing” with other people. Everyone has a voice in our cities. I look at the street as a place for ideas and expression, and I think it’s interesting that most people don’t. The street is public space, or at least it should be. Like in a weird way, I think the guy preaching the bible on the corner, the kid getting signatures for green peace, the dude playing drums in the street, and graffiti writers all have something in common—using the street to express ideas.

Image via Don't Fret

“Street artist” is sometimes a controversial term. Do you identify as one, or do you take issue with being identified that way?
Street artist is a word that sells T-shirts. There is a “street art” reality show. What most people now refer to as street art has essentially just become people legally painting murals. Some of these people have, in the past, done unsanctioned work and some of these people have never done any illegal work in their life, but call themselves “street artists,” when essentially they are (and I’m not fond of this term either) contemporary muralists. But “contemporary muralist” doesn’t sell T-shirts and “America’s Next Muralist” probably won’t do well in the time slot after Kardashians. Street art may exist as illegally placed public artwork or installation, but I don’t really like the term “street artist.”

The cities you depict have a traditional, 20th century vibe rather than the glassy modernism that many hipster neighborhoods have now. Is it a form of nostalgia?
Yeah, I think there is definitely some nostalgia in my work. The story in Chicago used to be steel and stockyards, and that is changing now. The neighborhood I grew up in is changing too, and I guess some of my street-scene paintings are looking back at the architecture, and the types of people and businesses that were in my neighborhood. Blending the past with the present and looking at how we got here and the pros, cons, and absurdities within all of that.

Image via Don't Fret

So you must notice some generational shifts happening. How are cities changing lately?
There are certainly more gluten-free options…

What role does social critique play in your work?
I think it’s a big part for sure. It certainly has accounted for a few hate mails from vegans.

Why do you work under an alias and keep your work anonymous? Do you still have to avoid trouble with the law even though street art has become so established?
I want my work to be about the ideas and the content, not about me. I consider what I do to be in a sort of legal grey area. I don’t think the characters I put in the street are particularly antagonizing, but I find it funny that some people find them antagonizing simply because of their placement in the street is illegal.

Who are your inspirations, both in art history and in the legacy of street art?
Ed Gorey, Jim Nutt, Chris Johansen, Woody Allen, Vaclev Havel, David Sedaris, and Barry McGee.

So you’re anonymous for artistic purposes. But can you tell us anything about yourself? How would you describe yourself? 
Vaguely. I’m a human from Chicago.

Image via Don't Fret