City landscapes have a way of offering up the unexpected—a hidden bar in a new storefront, or an alleyway that suddenly opens up where nothing was noticeable before. Street art heightens this sense of surprise by taking urban space as its canvas. Not only do graffiti and wheat-pasted posters give us narratives and characters that play out across city walls, they also heighten our attention to the context around them—the decrepit structures, the temporary construction walls, the bare brick of old apartment buildings. 

This sense of discovery is the most compelling aspect of the work of Don’t Fret, a Chicago-based street artist who works in wheat pastes as well as sculptures and standalone paintings. The pieces, which display urban scenes like vendors selling hot dogs, diners around a table, and trompe l’oeil storefronts, have a way of urging viewers to pay attention to their surroundings a little bit more. “I look at the street as a place for ideas and expression, and I think it’s interesting that most people don’t,” he says.

Don’t Fret’s style is rough and uneven by design. Like a skillful cartoonist, he knows when imperfection is perfect. The wobbly lines and obviously hand-painted colors of his pieces stand out in a world of glossy screen prints (Shepard Fairey) and omnipresent digital imagery. Here, nothing is airbrushed, nothing is Photoshopped. These are depictions of the city not in an idealized form—as in advertising or event posters—but as it actually exists at street level, for its citizens. 

The tone of Don’t Fret’s work is equal parts charming and poignant, hence the predominance of slight melancholy. A drunk in his underwear spills a martini glass. Anti-gentrification messages decrying brunch. The artist comes out of a tradition of painters who engaged with cities and people in the wild, as it were, capturing social issues as well as aesthetic ones. A touchstone might be Henri de Toulouse-Lautrec, who designed posters for ballets and theater stuck to the walls of early 20th century Paris, when he wasn’t sketching the insides of bars. The two share a populist impulse.

Don’t Fret is gradually moving off the streets, inhabiting neglected spots like an aging hardware store to create installations that move between artistic media. The format might be different, but the purpose is the same: to cause us to think twice about where we live, and the possibilities of an empty sidewalk.

Image via Don't Fret
Image via Don't Fret
Image via Don't Fret
Image via Don't Fret
Image via Don't Fret
Image via Don't Fret
Image via Don't Fret
 Image via Don't Fret
 Image via Don't Fret