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William Dolan's Art Captures Hidden Beauty Found Only in Chicago Alleys

 William Dolan's Alley Art
William Dolan's Alley Art
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William Dolan

“It isn't hard to love a town for its greater and its lesser towers, its pleasant parks or its flashing ballet. Or for its broad and bending boulevards, where the continuous headlights follow, one dark driver after the next, one swift car after another, all night, all night and all night. But you never truly love it till you can love its alleys too.” — Nelson Algren, “Chicago: City on the Make”

WEST ROGERS PARK — Growing up, William Dolan was a North Side alley kid.

“When I was younger I had to stay near the house. My mom didn’t allow us to go across the street, but we could play in the alley,” Dolan says.

“I grew up climbing on garage roofs and playing in old refrigerator boxes. I used to deliver newspapers in the alleys, pushing a cart to deliver the Tribune and Sun-Times. Alleys were always a big part of me.”

In the alley behind his parent’s apartment building, Dolan and his pals played “line ball,” Chicago’s version of stick ball, using a 16-inch softball adapted perfectly for alley play.

“We’d mark off lines in the alley for a single, double or triple. … It’s a foul ball if you hit it in a yard. Hit it in a yard that belongs to a nasty owner or a mean dog, and you’re out,” Dolan said. “I was never particularly good at it, broke a couple garage windows, but my friends liked it, and it was always fun.”

Now, the 53-year-old Grammy-nominated artist — Dolan designed the cover art for the Cathy Richardson Band’s “The Road To Bliss" album in 2003 — has returned to the very places he grew up to capture what’s left of “the old city” that you can still see behind apartment buildings, corner bars and bungalows in his pen-and-ink drawings exhibit “Alley Walk” at AdventureLand gallery in Wicker Park, 1513 N. Western Ave., this month.

 Grammy-nominated artist William Dolan's drawings of Chicago alleys are on display this month at AdventureLand Gallery in Wicker Park.
Grammy-nominated artist William Dolan's drawings of Chicago alleys are on display this month at AdventureLand Gallery in Wicker Park.
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Jesse Sioux

“Alleys are still part of the old city that’s unique to Chicago and tells the city’s story. A lot of the city is getting homogenized with flower planters, old buildings get torn down and replaced with condos, but the alleys are the same,” Dolan said.

“There are 1,900 miles of alleys, and so much going on in them. It’s an interesting slice of the city.”

Dolan’s drawings capture alleys along "L" tracks, behind police lines and a few of the childhood homes where he used to play. The show includes drawings of streetlamp-lit alleys marked with gang graffiti, blocked by police barricades, littered with trash, covered in snow, bookended by old and new buildings and even one that seems to disappear into Lake Michigan.

“All the alleys are empty because I want the viewer to be part of the scene. Put a person in there, and it becomes about the person. You react to the person. I want the viewer to feel present in the picture,” he said.

“In the drawings, the point of view is a bit higher than a person standing. It’s more like 10 feet off the ground … kind of like you’re almost seeing the perspective of the alley itself, if it were humanized.”

For Dolan, Chicago’s alleys always have been an important part of how he loves his city in a way Nelson Algren understood long ago.

“Those alleys,” Dolan said, “That’s basically where I come from.”

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