Andrew Winston’s Backstory

From the day I moved to Chicago I wanted to write a book about the city. Not just set in Chicago—about Chicago. It seemed to be an omen on my first visit that, according to the landlord showing me one apartment, Saul Bellow had written Humboldt’s Gift in that modest flat with its high windows facing the bus stop at Hyde Park Boulevard and 54th Street. A landlord dropping Saul Bellow’s name? I needed no further proof that this was the city for me. I decided to believe him, and signed a lease.

Chicago is a city that demands to be written about—but to be written about in a certain way. It is more pragmatic than newer cities and less self-involved than the older cities to its east. After all, this is a city that turned its river around and ran it away from Lake Michigan (where the city got its drinking water) so that industrialists could continue pour poisons into the stream. What is more darkly, more poetically American than that? To be in Chicago is to be closer to some essential quality of the American character, down where you can feel the engine throbbing, watch the cogwheels chewing away, and sometimes get your necktie caught in the gears.

I never did write a novel in that apartment. I lived in five more apartments in four other Chicago neighborhoods over the six years, from the southside to the northside. A crowd of characters collected in my head, and I made several false starts on books that tried to impose various styles and genres onto my diverse cast.

Then a friend working at a weekly newspaper asked if I would try my hand at creating a serialized novel á la Tales of the City, set in Chicago. Suddenly I saw a way to write a book as a tapestry of interwoven lives. The book would be about the process of people connecting and the changes they inflict on one another. I agreed and began mapping out a set of connecting stories on index cards using a complicated color scheme to create the warp and woof of the novel’s structure.

I sketched out seven storylines—a postman who stores undelivered mail in his southside garage, a Greek diner owner, a bunch of young hipsters starting a band (named Lather Rinse Repeat), two gay couples (one male, one female), a Jewish widow, and a Vietnamese-American boy and his mother. I had my melting pot, my seemingly simple starting point. I started writing, and the characters came rushing forward with their voices, desires, and petty preoccupations, as though they had been waiting for me to just start writing.

The paper’s managing editor decided not to do a serial fiction after all, but I was hooked and I kept writing. And writing. And writing. My wife supported me for almost two years while I spent more time finishing the book than making money. (You may be familiar with my classic work on the deep-fried onion blossom machine ad insert that came in your January 1999 credit card bill.) Over three years later I had completed an eleven hundred-page novel manuscript. Over the next two years I pared the book down to its current shape. (Much of what I cut out is on the book website.) I found a terrific publisher who believes in the book and now, at the end of the journey there is this teeming, rich book full of the stories that came to me through barstool conversations, news reports, and dreams. And it is, indeed, Chicago born.

Andrew Winston is a past editor-in-chief and fiction editor of the Chicago Review literary magazine. Looped is his first novel. His next book will be set in a different city that deserves to be written about. He can be reached via the Looped website

Comments

[deb]

I *just* finished this book. I got it from the library on a whim. I wasn't sure I would like it. But DAMN. It pulled me in and I could barely put it down to get any writing done. Thank you Andrew Winston. As a writer, you have given me something to think about.