‘Searching For John Hughes’ Author Jason Diamond On Finding His Own ‘Don Quixote’-Like Adventure

In 2009, Roger Ebert penned a glowing obituary for the director John Hughes that described the filmmaker as “the creator of the modern American teenager film,” Ebert credited his subject with “[establishing] an international notion of ordinary American teenagers” — especially since he, more than anyone else among his peers, “took teenagers seriously… as individuals with real hopes, ambitions, problems and behavior.”

Although his new memoir, Searching for John Hughes, is less about the storied movie director and more about himself, Rolling Stone sports editor Jason Diamond manages to turn the same descriptive lens Ebert praised in Hughes onto himself and his hometown idol. The new book, which goes on sale today, was originally supposed to be a biography about Hughes Diamond began writing in his early twenties, but that particular project never came to fruition.

What did happen, however, had a profound effect on Diamond’s personal life and professional aspirations. The young, inexperienced writer managed to overcome a broken home in Skokie, Illinois and develop a career thousands of miles away in Brooklyn, contributing to the New York Times, The Paris Review and The New Republic. And he finally got to turn his abandoned Hughes biography into something much more sweeter.

How does it feel that the book, which you’ve been working on in one form or another for a long time, is finally coming out?

I got one of those email questionnaires for an interview the other day, and it asked me how long it took to write this book. The short answer is a year and a half, but the real answer is a little over a decade, though I’m not really going to say that because it’s not totally true. It’s so fun and so great that it actually got to happen. I took the longest way possible to write this book. I would not suggest that to anybody, but I’m just really excited I got to do it. It’s not the book on John Hughes that 23-year-old me imagined I’d be writing, so there’s something kind of meta and weird about that, but I got to tell my story while discussing somebody whose work I really respect in a weird, interesting way. I’m just really happy that it got done.

Does the Hughes family know about your book?

I’m assuming they’ve probably seen something about it. They live in Lake Forest just outside of Chicago, and I think the book is getting some press out there. Since John Hughes is pretty well known, whenever a book has his name in the title I assume they probably hear about it. Also, one of his sons is a really good writer. I have a couple of degrees of separation from him. I’m assuming they’ve seen or heard about it, and I hope I get to talk with them — any of them. That’d be really nice. Once I go to Chicago for the book tour, they’ll probably hear about it then with the advertising blitz.

Is that director interview what ultimately inspired the book as it is now, or did something else happen to nudge you along?

I’d kind of had some ideas along those lines, that maybe I should write about this experience of trying to write a book. That, and framing it as a memoir about failure that would focus on the earlier years depicted in the book. I wanted it to be this silly romp, something much funnier than what I’d originally been thinking, though it wasn’t until after I wrote it that I realized it wasn’t as funny as I’d wanted it to be.