Jason Diamond (Photo: Elyssa Goodman)
by Andrew DeCanniere
Not long ago, I stumbled upon what has to be one of this fall’s best — and most engaging — reads, Jason Diamond’s memoir Searching for John Hughes (out on November 29th from HarperCollins / William Morrow). Earlier this month, I had the opportunity to chat with the author and Skokie native about how the book came to be, John Hughes and his work — and the role of Chicago’s suburbs in it — his influences, and much more. Read on to see what he had to say.
UR Chicago Magazine: I really thought that the way in which the book came to be was interesting. I mean, obviously John Hughes and his work had a significant influence on you, but it really seems to just have evolved organically, starting out as this idea that you brought up while out to dinner.
Jason Diamond: Yeah. That was really the pitch for the memoir. The initial idea for the memoir had stemmed from how I wanted to write about failing, how you could do everything wrong — how much I had failed and this kind of quixotic idea that I was going to write John Hughes’s biography. At 23 or 24 or 25 or whatever, I really wasn’t prepared to admit that writing a biography is this really massive deal. It’s not easy. You can’t just write it. I just sort of latched onto the idea that I was going to do that, and spent the next few years kind of getting a little obsessed. I mean, I was trying to do other things. Obviously, I was trying to work, I was trying to pay my rent. I was trying to figure out how to be a writer, but I just really thought that writing a biography was this magic bullet solution. You really can’t just jump into it like that. Looking back on it now, I kind of chalk it up to the fact that I was young and pretty romantic. Old school romantic about trying to do this thing I was passionate about, but didn’t really have any set idea. I didn’t sit down over the course of a few weeks or a few months to plan out how I was going to do this. I just jumped right into it. That’s something I wouldn’t advise for almost any endeavor, especially for writing a biography.
UR: It certainly sounds like it could be quite the daunting task approaching it that way, for one thing — to just jump into writing the biography like that.
JD: It’s kind of funny because a few years later, I read The Power Broker by Robert Caro, and I read other serious biographies. I started reading about what Caro does. I think he’s the biographer. I started reading about his process and how many years he puts into it. Obviously, that’s not every biographer. There are some biographers who can just get a bunch of information and put it into a book, and the book is out there, but that doesn’t necessarily mean it’s good. I just really had no idea — I read biographies growing up and I was just like ‘They seem pretty simple. I could do that.’ It was just a really silly idea, in retrospect. I’m glad I did try to do it. I could say that if I could go back and tell 23-year-old me not to do that, but I don’t think I actually would, now that I think about it. Maybe I’d leave it be. There are things we do in our younger years that we can look back on and go ‘I really screwed up my life by doing that.’ I don’t think I did that by trying to write a biography on John Hughes. However, I do think it was a little crazy, in terms of the way I went about it. Ultimately, I’m really glad I did. It was really hard, though. It was kind of like coming to grips with the fact that I wasn’t going to do it. Besides that, I’m happy I gave it a shot.
UR: And it’s just really interesting how that morphed into this memoir. The end product is a really interesting read.
JD: Yeah. It was really weird because I was playing with the idea of writing some sort of cultural history about the Chicago suburbs. I just tossed around this idea in my head. I was kind of actively researching it. Then I put it aside and was like ‘Nah, I’m not going to do this.’ Then I was working on another thing for another writing project, and it kind of collapsed on me. It just didn’t work out, so I was talking with my agent about it, and he was like ‘What do you want to do next?’ I was under the impression he was just going to tell me that we’re not working together anymore — that if I failed once, we’re done. I’ve been disappointed in myself and in life and in the things that I’ve done, but this was similar to the feeling when I finally started accepting the fact that I spent over five years thinking I was writing this biography, and that’s not happening. So, I thought maybe I should write a book about failing — specifically about me failing to do something. I think that we don’t like to admit it, but failure is what drive us and it is what’s super important to us eventually succeeding. I was joking where I told somebody it’s like a Larry David-esque take on my life. Look at this twenty-something in New York with his weird obsession and ignorant way of going about it. I’m really fascinated by characters like Oblomov and Don Quixote and Ignatius J. Reilly from Confederacy of Dunces. I kind of look back on my time and I sort of feel like there’s a reason I’m so obsessed with those characters. The reason is because we all have a tendency to be like that when we’re really obsessed with something. I had blinders on. So, I wanted to sort of turn the mirror on myself. When we started talking about the book, my editor was like ‘I wanted to know about your entire life,’ and I was like ‘Why would anybody want to know about my entire life? It’s me.’ As I started writing it, it really started to make sense to me how it sort of all fits together, and the finished book is that beautiful pink paperback.
UR: I also think that there’s a lot that people can relate to. There’s a lot that is unique, but I also think there are quite a few things that are universal. I think that for a lot of people in their late teens or early twenties there’s this sort of feeling of trying to find your place, of trying to find your people, and of trying to figure out what you want to do with your life. I think that regardless of your background or family situation, those are all things that many people will be able to relate to. They’re things that so many people grapple with at some point or other.
JD: That’s honestly the most important thing in the world to me, because I didn’t want it to be a book about John Hughes. I didn’t want it to be a book about my family life. I was really hoping that people would take away from it that you just have to keep going at it everyday. Things can be really bleak and crappy, and everything could fall apart, but you just have to kind of get back up and try your best. That the book is relatable is important to me, because when I was a kid all I wanted to do was relate to people and connect with people. I just longed for ways to connect with people. I thought about that going into writing this book. I would like to make sure anybody who reads it hopefully can connect in some way with something in there.
UR: The other thing that I found interesting that you said is that while it’s not a Hughes biography, you do mention that you did have this connection to his films. You say it sort of formed your view of the world and how you wanted life to be more like his films. The more that things didn’t go as planned, or the more off course they went, the more that seemed desirable.
JD: Yeah. Things go wrong in John Hughes movies. Not everything is great. People forget birthdays, people don’t love people back. All kinds of things befall people, but I think at the end of the day everything still works out. Everything is pretty good. It’s not perfect. I’ve never really been a believer in perfection, but it’s nice. A lot of his movies also happen to take place, essentially, in my backyard. So, it just became something I always connected with and went back to.
UR: And you allude to the fact there’s a sort of discrepancy between the world the movies portray and the reality of the suburbs — or, at least, your experience of the suburbs.
JD: Definitely. I mean, we can’t ask for the lives we’re given. I wasn’t dissatisfied with my life until I got a little older. I was like ‘This stinks. I hate everybody at school.’ As a kid, nobody was really teaching me how to live my life. I was going back and forth between my parents’ houses. A lot of the art I liked — which, back then, was comic books and John Hughes movies and Hardy Boys books and cartoons — fell by the wayside. The John Hughes movies stayed with me. It was just like having a comfortable space, watching those movies and thinking about those movies. A place for myself, really.
UR: You also learn quite bit about John Hughes and his work through the book. I feel like there’s a lot that you get to learn about him, as well. In fact, you talk a bit about how the Chicago area itself — and, in particular, the North Shore — takes this central role in his films. How it’s as much a muse as, say, Molly Ringwald or any other actor might have been. I just found that aspect interesting as well.
JD: I’m a big movie watcher and you have the French New Wave films that show Paris so beautifully. You have Woody Allen, who shows Manhattan so incredibly. You have Spike Lee, who shows Brooklyn. Obviously, LA has plenty of representation in films. I mean, there were movies set in Chicago and the Chicago suburbs before John Hughes was making movies, and there were movies set in the Chicago suburbs after he was making movies, but he sort of made it a thing. A couple of years before he did Sixteen Candles, you had Risky Business, which was set in Highland Park. You had Ordinary People, which is in Lake Forest. The way he shows Chicago in Ferris Bueller’s Day Off — and the way he shows the suburbs and the people living in the suburbs in his other movies — it’s really incredible. They’re not doing anything exceptional. They’re just living their lives. They’re a little silly at some points. I think The Breakfast Club is still incredibly relatable to anybody who has been to high school anywhere, but especially in the suburbs. I just think he did such a great job of that. I mean, it’s the Chicago suburbs, but I think it speaks to anybody who grew up in the suburbs anywhere.
UR: You also discuss the transition that film seems to have undergone, away from the suburbs to more of this focus on the big city. It may still be about the same time in one’s life, but the setting has sort of changed.
JD: Yeah. In the nineties, you start seeing movies like Singles and Reality Bites. They’re great movies. Those movies came out when I was a teenager. All of John Hughes’s movies came out when I was a little kid. There were some really great teen movies in the nineties, like Clueless and Ten Things I Hate About You, but he really turned it into an art form. The Breakfast Club could be a play. I mean, I’m really surprised that there has not been a serious adaptation to the stage. Ferris Bueller’s Day Off is such an incredible movie. I don’t mean to sell Ferris Bueller to anybody, but it’s really a great shot-for-shot funny and, actually, incredibly deep movie when you think about it. The whole idea is that you’re stuck with all of these people who want to hold you down — your parents, your crappy high school principal Rooney — and you just want to have a perfect day. That’s incredible. I wake up everyday, and at some point within the first hour, I think of that. I’m like ‘Man, I really want to try to have a perfect day today.’ You can’t, but Ferris Bueller totally wanted to, and that’s really a beautiful thing. I wish more of us could really think like that.
UR: I think that’s one of those that has really become something of a classic and, of course, with the holiday season coming up, Home Alone is another one. That’s actually one of my favorites.
JD: Definitely. And Home Alone 2. My wife is a few years younger than me. I saw Home Alone in the theaters when I was the same age as Macaulay Culkin, and she saw Home Alone 2 in theaters when she was about eight-years-old. That’s her favorite Home Alone, and I think that’s fair. I get that. If I were eight years old, and that was the movie I saw, I would’ve loved it, too. But Home Alone is just so cozy and Kevin McCalister is such a cool little kid. I love that movie. I watch Planes, Trains and Automobiles everything Thanksgiving — I write about that in the book — but I also watch Home Alone at least twice around the holidays every year.
UR: I actually saw Planes, Trains and Automobiles for the first time in a long time last year or the year before.
JD: I mean, when he got to work with John Candy — even John Candy’s character in Home Alone — it worked out really well. That movie, to me, is just so great. Steve Martin’s a genius. You just can’t really beat it.
UR: I know that you touched on it somewhat earlier, but if you can sum it up, I was wondering what you hope the takeaway from your book would be.
JD: I was thinking about that, and it all boils down to cheesy cliches. People can tell you that you can’t do something, or you may think that you can’t do something — and maybe you can’t. You might not be able to do that one thing. You might not be able to write that biography. People always say ‘I really wanted to be a writer.’ And I’m like ‘You could be a writer.’ I know it sounds really simple, but you can. You might not get paid a lot for it, but you can write. There are places you can write, there are things you can do. If you really want to do something, you should go for it. It’s total high school football coach corny kind of talk, but it’s so true to me. You might not get exactly what you want, but you’re going to get something out of it if you just keep working. Also, know your limitations. At the end of the day, you have to know when to hold them and know when to fold them. If you’ve been trying to write a biography for five years, and it doesn’t look like it’s happening, you might want to put it in the desk for a few years and think about it. That’s really it.
UR: Who would you say your influences are? Who are your favorite authors, or which are your favorite books?
JD: Nora Ephron is probably one of my favorites. I also love Joan Didion. In terms of fiction, Saul Bellow, F. Scott Fitzgerald, Edith Wharton, James Baldwin. There are a lot of writers that I love. I don’t know if I could necessarily call them all influences, beyond the fact that their writing inspires me. There are so many of them.
UR: I can certainly relate. I think it can be kind of hard to really narrow it down.
JD: I think that if I go with anyone, I’d say it’s Nora. I saw Nora Ephron’s movies and started reading her essays. I was like ‘This is something I’d like to shoot for as a writer.’ There’s just this honesty. The writer tries to laugh at themselves, but also can be honest and emotional and still good. I try to be honest with whoever is reading my stuff. I’m trying to be open with them. I like the idea that if somebody reads something I write, they’re like ‘Oh, yeah. I can see hanging out with this guy and talking to him about it.’ I like connecting with people and I like my writing to be accessible.
Jason Diamond is a writer and editor from Brooklyn. He is an associate editor at Men’s Journal, a columnist at Electric Literature, former literary editor at Flavorwire, and the founding editor of Vol. 1 Brooklyn. He has been published by the New York Times, The Paris Review, New York, The Believer, The New Republic, the New York Observer, Tablet, The Rumpus, The Awl, and in many other places.
For additional information, visit the. You can also find Jason on both and .
At press time, upcoming appearances in the Chicago area include the following:
2421 N. Milwaukee Ave.
Chicago, IL 60647
Monday, December 5, 2016
7:00 PM - 8:00 PM
Jason Diamond with special guest Megan Stielstra, author of Once I Was Cool
4736-38 N. Lincoln Ave.
Chicago, IL 60625
Tuesday, December 6, 2016
You can also find a complete listing of all scheduled appearances by.
This interview originally appeared in Chicago Splash Magazine.