Jason Diamond Credit: Elyssa Goodman

The title of Jason Diamond’s new memoir, Searching for John Hughes: Or Everything I Thought I Needed to Know About Life I Learned From Watching 80s Movies, is deceptive—it suggests a series of cheerful reminiscences about lessons Diamond learned from Ferris Bueller’s Day Off and The Breakfast Club and how he applied them to his own life. But Searching for John Hughes is both darker and more interesting. Diamond grew up mostly on the North Shore, close to where Hughes lived and set his greatest sequence of films, from Sixteen Candles in 1984 through Home Alone in 1990. These movies (especially the ones about teenagers) had a huge impact on a generation of kids who, like Diamond, grew up watching them on TV and believing they were an accurate representation of high school life.

During a dismal period in his 20s, Diamond decided he would make his name in literature by writing a biography of Hughes. Searching for John Hughes chronicles Diamond’s misadventures chasing after the director and everyone connected to him. The book also looks back on Diamond’s even more dismal teenage years when, after he was legally separated from his abusive father and abandoned by his mother, he spent three years essentially homeless, staying with whichever friends and teachers would take him in.

Now Diamond is 36. He lives in Brooklyn with his wife, two cats, and a dog. He’s the sports editor of Rolling Stone and the founding editor of the website Vol. 1 Brooklyn. It’s probably not as dramatic a happy ending as Hughes would have written, but Diamond seems pretty satisfied with it. We had a lengthy conversation a few weeks ago about the book, growing up in the Chicago suburbs, and 80s and 90s pop culture.

Aimee Levitt: So how did you come to write the book?

Jason Diamond: I sort of had been hitting a wall professionally: I had an idea for a book that nobody wanted. My job was terrible, it was the middle of August in New York, I really felt like I was failing, and I was very disappointed in myself. And I started to think about the last time I felt like I had failed so spectacularly, and I finally came to this realization that trying to write a John Hughes biography was kind of not my thing.

And I started thinking about how with a lot of the books I love I’m always attracted to these characters who are totally ignorant to how silly they’re being: Confederacy of Dunces, or Don Quixote, or Oblomov. I thought, “Oh my god, I was totally one of those characters, trying to write this biography.” And then I was like, “Maybe I should write a book about that: about failing, a memoir about myself failing.” When I presented it, people were into it.

The editor we ended up going with said, “I want you to write about your entire life.” And I was like, “Why?” But then I started sketching it out, and one of the things I eventually started realizing was, “Oh, this all kind of ties together perfectly—it makes sense!” My obsession with his movies, and where I grew up, and all that stuff. And so I just sat down and started writing, and pretty early on it came together like that.

I think it would be hard to make a lot of that stuff funny, especially the teenage stuff.

I sort of said, “I got to balance this as best I can, and try to be like, ‘Hey, I hope people realize that I kind of realized that I was sort of a twat when I was getting older.’ ” But I also realized that I write about some really heavy stuff. So I was trying as best I could to lighten that, because I don’t want to bum anyone out too much. When friends started reading the book, they were all, “I never knew all of this about you,” and they would say, “it made me cry,” and people started tweeting to me, saying I was making them cry, and I was like, “Oh my god, I don’t want to do that.”

It made me cry. I think it’s just something about abandoning a child. When you’re a douche in Brooklyn, that’s one thing, but a kid just being forced to be homeless—that’s tough stuff.

Yeah, it’s weird. It’s hard because my wife was the one who told me, “You were neglected.” And I was like, “No I wasn’t, I was fine! It was cool! I was an angry punk-rock teen! It was great! Yeah!” And my mom and I still don’t really have much of a relationship to this day. I was a total screwup; I was a pretty bad kid. But it was also pretty hard for me to find my way. Thankfully I was resourceful enough that I did, but it was really hard. And only in the past two years I’m like, “You know, the people who knew me when I was 18, 19, even probably into my early 20s, knew this terrible, obnoxious person who got drunk a lot and didn’t really have any friends, and a lot of that was because I was kind of still stuck in this mind-set of being this 16-year-old kid.” And it took me a really long time for me to put all this together.

You kind of get into it in the book with John Hughes movies, where these kids always have these beautiful homes to go back to, but their parents are awful.

Yeah, they always have something. But there’s always trouble. There’s always problems in Shermer, Illinois. The boy or girl doesn’t like them, or the parents forget their birthday, or they’re John Bender and things are really terrible.

But I don’t know, there’s always a happy ending, you know? Portraying suburbia as this very white, very ultimately happy place is kind of false. But that was what he wanted to do. And, you know, I held on to this idea that things would really get better if I stayed the course as best I could. That course was kind of yanked—I was sort of pushed off that course at an early age—but I didn’t totally recognize that because I was just trying to be a kid.

Do you still watch John Hughes movies?

Yeah, I’m actually going to watch Planes, Trains and Automobiles tonight. But I haven’t for the last few months, and it was kind of because it was a detox thing. And whenever Ferris is on, I’ll still watch it because it makes me feel good.

That was my favorite John Hughes movie, I think.

I’ve been running into a lot of people who have been saying the same thing, and that’s interesting to me, because I think we associate more with different movies. The whole scheme to Ferris Bueller is just have a perfect day and screw anybody who wants to hold you back from that. And that’s really nice, to try to have that one perfect day.

I think the thing that I liked about Ferris Bueller was that it was a one-perfect-day fantasy. You knew it would never happen. You could imagine The Breakfast Club happening, with you bonding with people who are unlike you in detention, but that never happens. With Ferris, you already knew it would never happen.

I don’t know if you’ve ever done—actually, I’m going to say you’ve probably never done this, I think I’m just a weirdo, but there are so many good fan theories about Ferris Bueller, and my favorite one is that it’s just all imagined through the eyes of Cameron.

Oh, I like that!

Yeah! He’s just imagining Ferris. Somebody was comparing it to Fight Club, and I’m like “That’s so weird, but it’s so awesome that he actually took the time to write this detailed Reddit post about that.”

I kind of did the same thing when I was writing blog posts about John Hughes. You know, people want to unlock this; somebody was comparing it to magical realism. That’s awesome to me, because something I always felt was that John Hughes’s films are sort of preserved from the 80s, and they’re about teens, and the happy endings, and the whole thing—and I think people are like, “He’s not serious.” And now you’re really starting to see people break apart his films, and I think that’s an important step in the critical process.

I think there are a lot of people like you too, who grew up with him and are starting to take him seriously.

There are a lot of people who grew up with him in different eras, and I find that really fascinating, how people from each era take different things from his movies. And it’s sort of boiling down into one career. It’s not just the 80s, or Home Alone—it’s the whole thing.

You mention the great movies of the 80s, and then his kind of sellout period, the Disney period.

Yeah, I wrote this thing for the Atlantic last year about how Home Alone sort of ruined him. I was theorizing, in a way, that he had kind of grown weary of the establishment critics just panning what he did, and what he loved to do, which were those earlier movies. And he was just like, “You know what? I’m going to make money.” There’s no two ways about it. He was a smart businessman and he was an ad guy—he knew what he was doing.

Yeah, Home Alone has everything: the cute kid, the slapstick, the Christmas.

I’m really glad you say that, because I maintain it’s a great slapstick movie. I love how now there’s an Onion-esque take on everything—you see people writing these satirical articles about Kevin McCallister, “Winnetka boy found guilty of murdering 20 people.” People are writing fan fiction about him, like how he became a serial killer, and I’m like, “Yeah! Totally plausible!”

He totally had it in him.

Oh, he was a psychopath! He was nuts! Totally demonic! One of the original American serial killers is from Chicago: H. H. Holmes. And he had this house of torture. You can totally place Kevin McCallister there. You can rewrite Devil in the White City. Maybe I’ll do that! Yeah, that could be my million-dollar idea!

I was researching Lost Chicago and all that stuff. I love Chicago. I know it’s got its problems, like any city. Chicago’s problems have been highlighted because of the election. You know the writer Rich Cohen? He has this thing about how New York has a foot in Europe and Chicago is the great American city. If I could live and survive in Chicago, tomorrow, if I could give it all up and go back, I would. I feel more comfortable there than I do in New York most of the time.

Part of living in New York is feeling uncomfortable all the time.

Yes! That’s it. You’re a total masochist. It was nice kind of really immersing myself in the culture and the memories and the history of what makes Chicago and the suburbs of Chicago so interesting to me and so fascinating.

Did you go back a lot when you were researching the book?

Yes, I was back a lot. I think I went four times. I have this website that I do [Vol. 1 Brooklyn], and we were doing an event at Pitchfork, and I think it was like the Saturday of Pitchfork, and I’m like, you know, I’m just going to go for a drive. I rented a car and I went all the way up to McHenry County. I went to Skokie, I went to Evanston, I went to all the places I’ve lived. And I ended up all the way in McHenry County, where it was sort of like end of the line, because my mom had lived there for a while, but this is as far as I’m going. There’s nothing past here for me. Then I did the drive back, and I took my time. I didn’t get on the highway. I even went to the cemetery where John Hughes is buried in Lake Forest.

Do people leave tributes on his grave?

No, not really. It was kind of shocking to me. It’s actually a beautiful cemetery. I’m cheesy and sentimental, so I think when I come to Chicago on the book tour, I might stop there and lay some flowers or something.

Maybe you’ll start a thing, like the way people started laying green apples on Harry Caray’s grave during the World Series.

That makes me emotional. I didn’t know that. Of all the Cubs stuff, because my day job is as a sports editor, I didn’t know about the green apples thing. That gave me a little chill just now. But I left a pen on Herman Melville’s grave, so I’m part of that, I guess.

No, it’s a nice thing, I think. Letting people know stuff is happening that they might want to know about.

Part of me is hoping that someone in his family gets to check out the book, and hopefully they like it. I’d like to let his family know that their father or their husband really impacted a lot of lives and took it to the extent that they would write a whole book about it.

I wonder if he knew that when he was alive, how much his movies meant to people.

When I originally started planning the book, I had written a lot of stuff theorizing about that. Because I know there’s the J.D. Salinger comparison that people like to make; I don’t know if it’s valid. But the way people went to Salinger and were like, “Your books really taught me about the world! Your books changed my life!” And he didn’t want to hear about it.

You know how when you watch The Simpsons and they show this entire map of Springfield? Or any other little self­contained fictional world? I have this hope that there’s this whole backstory to Shermer.

That would be amazing.

He actually said himself that John Candy’s character in Planes, Trains and Automobiles lived down the street from Bender from The Breakfast Club. It all connects. That’s just my one big last John Hughes dream, is that we find out the daily lives of these people.

What if your book were responsible for a whole John Hughes revival?

That would be so weird. If my book is responsible for anything, I hope it’s that people really start rewatching his movies. . . . I mean, his movies are always on. It’s not like I’m reviving a lost novel that didn’t get the respect it deserved or some soul album from the 60s that no one ever heard. I’ve seen the Cubs win a World Series, but I would be totally stoked if people would be like, “We really need to rethink this guy’s movies.” I would think I would’ve done a good job in life if that happened.  v