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Author Interview | Jason Diamond is “Searching for John Hughes”

New memoir traces impact of John Hughes' films, Chicago suburbs, and the Cubs on author's life.

Erica Riveraby Erica Rivera
Photo: Elyssa Goodman.

Searching for John HughesIf you came of age during the ‘80s or ‘90s, you’ve likely seen a John Hughes film, whether you intended to or not. Jason Diamond didn’t just watch them– he studied them and longed to embody the world of bumbling, adorably flawed teens from classics like The Breakfast Club, Pretty in Pink, and Ferris Bueller’s Day Off.

Diamond’s new book, Searching for John Hughes, is not just a fan’s elegy to the late, great writer and filmmaker but a memoir framed by the influence of Hughes’ films in Diamond’s life and how he sought escape through them. The author’s own story of wayward adolescence in Chicago’s suburbs at the end of the 20th Century is every bit as nuanced and tenderhearted as the films that so captivated him in his youth.

Diamond now lives in New York and is the founding editor of Vol. 1 Brooklyn and sports editor for Rolling Stone.

Crave: What about John Hughes’ films resonated with you?

Jason Diamond: When I was a kid and I watched them, I instantly was like, “I know where that is. I know where these movies are being filmed.” Seeing what looked like my backyard instantly grabbed me. From there, I just started watching his movies; they’d be on or the babysitter would bring a VHS tape over, and I’d be like, “This is cool. This is what I imagine being a teen is like and what normal families are like.”

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Do you think Hughes’ movies have withstood the test of time? Do they still make you feel those feelings when you watch them now?

Yeah. Obviously, there’s a little bit of a difference because I’ve immersed myself in so much research about his movies and his life. I still find myself going back to them when I feel like I need something, when I’m feeling down, when I’m feeling out of it, I’m going to watch “Ferris Bueller” or “Home Alone”. The movies are like an old friend.

In the book, you write, “I used those John Hughes movies as my road map for life. You should never do that.” Why not?

Escapism. We take movies or books or things that we like and have a few hours where we don’t have to deal with the drudgery of life and all those terrible things that are always happening. I think I took it a little further. When I started seeing those John Hughes movies when I was a kid, I was like, “I really want this kind of life.” In those movies, there was some strife, and people had family problems, but to me, that looked so normal. That’s what I wanted to reach for, to get to a place where problems could float away at the end of the day and everyone’s happy. I really wanted that because my family life was so not any of that. I was like, “Maybe if I pay attention to these people, one day I’ll be like them.” They’re movie characters. They’re fictional creations. You’re not going to be like them. I had to learn that. It took a while.

Is there one character that you particularly connected with?

I think Allison from “The Breakfast Club”. When I first saw that movie, I could see a lot of myself in her: the teen who is obviously different and relishes being different. As a kid, I really wanted people to like me and wanted people to talk to me, but I was so awkward and weird, I didn’t know how to be like, “Hey, let’s be friends. I’m not so weird.” As a kid, I looked at her and identified with her because she’s the goth weirdo of “The Breakfast Club”. As I got older, I realized it was deeper than that.

Do you think there’s a comparable filmmaker now?

It’s so hard to write those kinds of stories this day in age. John Hughes was sort of like a place and time. He was somebody who knew how to pull people’s heartstrings. He could be sappy and it worked. And I don’t think sappy works as well these days. And that’s fine. There’s only so much sap we can handle.

It’s interesting that he captured adolescence so well even though he was writing from an adult perspective.

That’s something that people have always been fascinated by. First things first, he was a writer. That’s how he saw himself. I think that’s why people connected with him. I don’t mean to compare him–because the comparison has been made a thousand times–but the J.D. Salinger comparison does make sense to me because he wrote about young people in a way that really resonated, and then what did he do? He up and disappeared.

Did Hughes inspire you to be a writer?

I didn’t really realize, until I wrote this book, how much he has inspired me as a writer. I don’t know if he inspired me as much to become a writer but he definitely inspired my writing in a lot of weird ways. I think my Midwestern side comes out a lot in the essays I write and the subjects I want to focus on. I’ve read a lot of his writing for National Lampoon and it’s sexist and crude and not really my thing, but he definitely is an influence on me. The stuff he created is in what I do.

When I read the final version of my book, I was sort of like, “Yeah, I can kind of see a big John Hughes influence here.” Which is kind of funny because I wasn’t going for that. Except for the happy ending. I wanted to leave it off with a happy ending because I always thought that was a John Hughes thing.

Your story could be a movie. It has all of the cinematic elements.

My wife made a joke about that, but I don’t think so. I wouldn’t want to see that. I don’t think I want to see anything I ever do on a screen.

You talk about the importance of the Cubs in terms of the culture of Chicago in the book. It seems timely given that the team finally won the World Series. How do you feel about that?

Oh my God. It’s insane. I was watching the game the other night and as soon as it was over it dawned on me: I just saw the Cubs win a World Series game! I don’t want to sound like a total jock or sports nerd, but one of the last things I remember talking to my grandfather about before he died was the Cubs. I have a lot of bad family memories, but a lot of good family memories are about the Cubs. I’m a massive, die-hard Cubs fan. It’s super intense.

I keep joking that I couldn’t have fit more into one month: I’ve got the Cubs in the World Series, this crazy election, and my book comes out.

It’s all happening.

Yeah. I might need a break.

What would you say to Hughes now, if you could?

I would thank him. I live a life where I’m surrounded by books and movies and I listen to lots of music and I’m inspired by a lot of art that I love, but his has lasted and his has impacted me more than anybody else I could think of. I have some issues with his films that I get to in the book. There were certain things that, as I grew older, thought, “That’s bad.” Like Long Duk Dong and the Jake Ryan rapey teen in Sixteen Candles. But I would tell him “Thank you.” I have few regrets in this life but I really wish I could have told him that.