A while back, Aaron from the Dial Bookshop asked me to do some more Chicago author portraits for the store. I had done one for each month last year, but the wall they hang on had some room near the ceiling, so, out of horror vacui or completism, Aaron thought we should fill the rest of it. The six subjects I came up with are a mix of dead and living writers. Some I know well; others, hardly at all. Ben Hecht is probably closest to my heart for his 1001 Afternoons in Chicago and for The Front Page (even more so for the film His Girl Friday, which was inspired by that play.) Hecht is an outsized Chicago personality and a fun subject for a painting. 

On the opposite end of the spectrum is Leon Forrest, a writer I’ve always meant to read but haven’t gotten around to. Searching around for reference photos, I could only find two or three of the man. It made him that much more inscrutable. I took his epic, Divine Days, out of the library after finishing the painting, but have been a little intimidated to crack it open. 

Congress Parkway, which runs south of the Fine Arts Building (where the bookstore is), was recently renamed after civil rights activist and journalist Ida B. Wells. Aside from that link, the first thing that comes to mind when I think of Wells is a dim memory of picking up cab passengers in the remnants of the housing project named in her honor. They’re all gone now. 

All I know about Sara Paretsky is that she’s a famous and successful detective/mystery writer and that she’s a snappy dresser. I know there was a Kathleen Turner flick based on the heroine of her books, but I can’t recall a thing about it.

Alex Kotlowitz is a writer I admire very much. I loved his last book. It’s a little weird to switch gears from rendering someone like Paretsky—whom I never met and probably never will—to Kotlowitz, who I’ve talked to a few times and who may actually read this letter. But he’s one of the best writers this city’s got, so I couldn’t leave him. 

Stuart Dybek is another complicated one. I count him among my favorite writers from anywhere and I had the privilege to illustrate one of his stories awhile back. We’ve corresponded a bit too. But I couldn’t or wouldn’t call him a friend. He exists in a hazy in-between region—drifting from unapproachable master to humble and witty penpal. I don’t know how to think of him but think everybody should read his stories. Few have evoked Chicago more poetically or precisely.