Jason Diamond is a fixture of literary Brooklyn. Founder of Vol. 1 Brooklyn, sports editor for Rolling Stone (with stints at Men’s Journal and Flavorwire before that), and owner of a spectacular beard, Diamond is instantly recognizably and widely loved—as a writer, as an editor, as a literary citizen, as a mensch. His debut book, Searching for John Hughes, comes out today, and so Diamond and I talked via email about his memoir, about New York and Chicago, and about the events he has coming up this week: tonight’s book party at Book Court with Danielle Henderson and two bottles of Malört; Wednesday’s “The Greatest Three Minute Teen Stories Ever” at Housing Works. Go!

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This memoir is about a lot of things (not least of which is the titular Hughes), but it’s also so much about home and place. You’ve created an evocative portrait of both the Chicago of your childhood (and adulthood), and of New York City in the aughts. What is your relationship to Chicago today? To New York? What (and where) do you call home?
Can I claim dual citizenship? I have a hard time seeing myself living anywhere other than New York City because I’ve been here so long, got so used to its pace, and also because I’m pretty much not employable anywhere else that I know of. Chicago is my hometown. I root for the Cubs and Bulls, I still say “jagoff” all the time, and I’d rather put cyanide on a hot dog before I’d put ketchup on it. That said, New York was a place I dreamed of living in as a kid. Now I sometimes daydream about going back to Chicago. I smell certain things in the air or hear a song and I’m back there. But I don’t think I’d be able to do it. I love visiting a few times a year and discovering and rediscovering things that make the city great. People sometimes need to get out of their hometowns no matter how great they are.
Another subject you tackle is failure, or—rather—how what we want sometimes changes. The seed of this book was planted when you first began work on a John Hughes biography, now you’ve written a Hughes-laced memoir. What was it like walking away from the first book?
It was really hard, but I learned a lot from failing. I think we’re so quick to tell kids that you can do whatever you want to do if you put your mind to it, and while that’s great, it’s actually not that easy. I’m a bigger fan of the “learn from your mistakes” bit adults tell you when you don’t succeed. I think you have to fail a lot to accomplish anything, and I did plenty of that. I think part of my big problem was I kept trying to walk away, but couldn’t. I kept interpreting things as signs and feeling like I was on the right path when I really wasn’t even close. I really had to find something to focus my attention on in order to move past because, looking back on it, I think I was using the idea of a John Hughes biography as an excuse to justify my existence. I just wanted to feel like I was doing something.
You also talk a lot about your family here, recalling stories that are both difficult and painful. How did you tackle these revelations? How much time did you spend, if any, thinking about how making these stories public would affect you? How they’d affect your family?
I actually got really mentally trapped dwelling on a lot of the things in the book. It wasn’t hard for me to open up about them, but writing them, then rewriting over and over, trying to make these things readable for whoever might pick up the book, was a really strange process. That, and really having to really think about things I didn’t really want to spend a ton of time thinking about, for days and sometimes weeks, really triggered my depression more than a few times. It was hard.
I’m not really close with my family so I couldn’t say how it’s affecting them. If they’re hurt or offended by anything I wrote then I guess I’d understand, but this is my book and my story. Now that I’m a little older, I’ve put myself in a place where getting along with my family in some capacity is possible, but I’ve spent over half my life estranged from one or both of my parents in some way, so I guess I probably won’t come that close to having many “normal” family relationships. That’s something I’ve had to really admit to myself.
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Another big theme of this memoir is survival: surviving your father’s violence, your mother’s absence, homelessness, being without medication, poverty, the loss of people who stepped in at various points to care for you. This is really the heart of the book, but I’m interested in hearing how you’d describe it in sum. How did you survive?
I honestly think it’s a combination of stubbornness and hope, but sometimes I also think those two things are sort of the same, or maybe that they’re tied together. Like you have to be stubborn to keep having hope. I’m also endlessly curious. Things always make me think that yeah, the world could be garbage, but there is always something new for me to obsess over. Some book or movie or something.
Tonight, at Book Court, is your first book party—an event you describe dreaming about many times throughout your memoir. How does it feel now that it’s actually happening?
It’s so weird. I’m definitely really nervous. Last night my wife pulled off the ultimate night-before-my-book-party surprise karaoke party with a lot of my closest friends and it took some of the edge off. I couldn’t have asked for a better new chapter to the book of my life that I’m always writing, and I hope tonight will be just as fun.

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