Skyscraper City: The Jason Diamond Interview

by Royal Young

When I get to The Breslin, Jason Diamond is already two drinks in. I’m sweaty, having gotten lost in the maze that is the ACE Hotel basement. I blurt that my father is from Chicago. Diamond orders me a drink. He is immediately relaxed, perhaps momentarily forgetting about his duties as Editor-In-Chief of Jewcy and founder of Vol. 1 Brooklyn, as he talks about his native city.He speaks of The Loop, the lakes, the suburbs, driving into the Lower East Side with his father after his parents’ divorce to find the best Kosher chickens from a run down Orthodox butcher. Almost fifty years ago, my own father fled Chicago to defy his crazy Hebrew clan and his bland, unhappy Midwest roots. My father dreamed of becoming a famous artist in New York and for a moment, he was.  Now, surrounded by the clink of glasses and rustle of expensive suits and shiny dresses, it seems Diamond and I are drinking in the classy American establishments our immigrant ancestors never had. Diamond and I talk about success, something he is familiar with, tirelessly exploring thrilling ways of channeling his creativity. From the publications he curates to readings, events and his own irreverent, nostalgic and hilarious writing.

Diamond and I discuss visiting Philip Roth’s summer home, the city he loves, public humiliation and a little advice.

HOLY DIVER: Did anything especially tragic happen during your childhood that attracted you to writing?

Jason Diamond: I guess less tragic, more traumatic was that my parents got divorced when I was pretty young.  I spent most of my childhood being shuffled from two different households.  My mom also moved to a new place every year, so it made it really impossible to make friends.  I was pretty awkward growing up, so I read a lot from a really young age since the books I read didn’t judge me like I felt most people did.  I think from there, the next logical step was to start writing.

HD: Could you describe some of the landscape you grew up in? How does Chicago and music fit into your own life and work?

JD: Oh jeez, that could fill a novel.  My mother’s side of the family has been around Chicago for a long time, so I’ve always felt a connection to the city and the suburbs around it.  I’m working on a non-fiction book that focuses on four women who grew up in a neighborhood a few miles north of the city, and besides the story itself, I’ve always believed the North Shore of Chicago (in the book’s case, Lake Forest) is a really special place that could lend itself to any work.  But Chicago as a whole I’m fascinated with due to the strange history of the city.  Books like The Devil in the White City by Erik Larson and Sin in the Second City by Karen Abbott really are fantastic works that focus on the period I’m most interest in, but then there is so much more to read about.

As for music, it’s the same as books and writing.  I never played music, so listening to it became another escape from all the weirdness of the world, and my own personal inability to relate to people around me.  But I’m also good at remembering things, so I created a pretty good mental library of music I liked, and who played with what band, what label put out which record.  I also have really varied tastes; I could listen to something composed by Nico Muhly while working, then switch it up and listen to Minor Threat or something like that.  I think that is one of the reasons I’ve had some success as a music writer.