‘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.

Through it all what I was mainly thinking about were books like A Confederacy of Dunces and Don Quixote, in which the protagonist is totally ignorant to how silly they’re being. They go on these quests they think they’re totally right to do, but they’re actually not. I was acting like those characters at that point in my life, and I wanted to write about that, so I did. Larry David is also a big influence. You know, like when you totally think you’re in the right but what you don’t realize is you’re alienating people. That’s what I was doing.

You tend to structure each chapter around one or two particular Hughes films. Was this your intent while writing the book, or did it just happen?

It was kind of organic. I don’t know if you could really say “kind of organic” about anything, but as I was writing it, I would envision the particular part I wanted to write about. It would just pop into my head and I would immediately think it was similar to Home Alone, Sixteen Candles or whatever movie came to mind. Sticking with a particular theme was important, so I figured I’d stick with those comparisons and make them work. Honestly that was kind of my intention to begin with, with writing a memoir, since so many memoirs are crap.

I’m not trying to degrade memoirs, but the great memoirs are the ones where people actually write their stories, their lives, in an interesting way. That’s the challenge I faced, because I’m not the most technically savvy writer. I’m not a wordsmith. Not going to dazzle you with my prose, so I needed to figure out a way to tell my story in an engaging way. Framing it via Hughes’ movies, and how they specifically connected to me during the times I was writing about, would do that for me.

Reading the book felt like watching the beginning of a Hughes movie, to some degree. The reader follows you, as one of Hughes’ downtrodden, misunderstood teenagers, as you struggle with writing the book and trying to make a name for yourself.

It’s a real thing. We’re taught from an early age we have to do things a certain way. We’re taught from day one, when we start learning things, you have to do things this way in order to be happy. It’s this crazy thing, and I heard all of that growing up — you have to go to college, you have to get married, and all that. Still to this day, I’ll impose these mental signposts, telling myself I have to be better, do better and be great at whatever I do. I’ve nearly killed myself trying to accomplish this, but somewhere along the way I learned it’s okay to go in a different direction, away from the path you’re told to follow.

You often recount watching certain Hughes films throughout the book. Sometimes it depends on the time of year, others in regards to what you’re experiencing then. Are you still able to watch Hughes as much these days?

I can still watch them. The funny thing about his movies is they’ve become dependent on my mood. If I’m feeling a Breakfast Club kind of day, then I can totally watch that. Every year around this time I watch Planes, Trains and Automobiles. I don’t think that’s ever going to change. I’m probably going to watch Home Alone next week. I watch a lot of movies, but I can always go back to John Hughes.

When you really don’t have a home growing up, these things that you love — these books, these movies — they can kind of become your home. You can go back to them and they’ll make you happy. His movies still do that for me. I’ve been able to look at them from every possible angle, and I’m very happy I’ve been able to do that and still feel the way I do. There are things I’m still not happy with in certain ones, but that’s home. That’s family. You’re not going to be totally satisfied, but I’m glad I can always go back to them.

Searching for John Hughes is now available in hard copy and digital editions at Amazon and wherever books are sold.