Jason Diamond’s debut book wasn’t supposed to be a memoir. The writer and Rolling Stone sports and culture editor started out trying to write a biography of his childhood idol John Hughes , director of the films “Home Alone,” “16 Candles,” “The Breakfast Club,” “Pretty In Pink” and “Ferris Bueller’s Day Off” and the hero of Diamond’s hometown of Chicago.

The project didn’t go anywhere, but it provided the inspiration for “Searching for John Hughes: Or Everything I Thought I Needed to Know About Life I Learned From Watching '80s Movies,” Diamond’s memoir, published in November by William Morrow. The book recounts Diamond’s troubled childhood in the Chicago suburbs, his experiences with homelessness, and his quixotic quest to write Hughes’ biography while working selling coffee and cupcakes in New York. It also takes a look at the iconic ‘80s comedy films that got him through it all.

Diamond spoke to The Times via telephone from New York, where he lives.

Can you explain how the book changed from where it began?

I had been on kind of a losing streak professionally, and I was feeling really defeated about a lot of things. I got to thinking about the last time I had felt so down, or if there was something I could recall that was even worse. And I immediately clicked back to when I came to this realization after several years that I'd been trying to write a book that I had no business writing. It's a pretty hard thing to accept. So that started making me feel a little better, and I started thinking, "Maybe I should write about that." I've always been into books like [Ivan Goncharov's] "Oblomov" and [John Kennedy Toole's] "A Confederacy of Dunces," because I have a tendency to be like those Don Quixote kind of characters who think they're supposed to do something brilliant and big, and they're acting kind of crazy without realizing it. I wanted to write something like that, because that's how I looked at my life for those couple of years. When I started talking to editors, the one I liked the most was like, "I want to know about your entire life," and honestly, [the idea] had never even dawned on me until that moment.

You had a difficult childhood, a difficult young adulthood. What was it about John Hughes' movies that helped you get through it?

I'm a sucker for — I always say "happy endings," but it’s not just happy endings. I like the idea that things can be better than they are. People read the book, and they're like, "Man, you had such a rough childhood," [but] the weirdest thing is that I'm the most positive person. I look at the bright side of everything. I joke that it's because I'm Jewish and a Chicago Cubs fan, and up until last year, it was like those two things meant, "Losing!" [Laughs.]

I feel like at their core, that's what [Hughes'] movies are about. Things are better than they are. You think your parents aren't going to remember your birthday, but they'll come downstairs and your dad will softly remind you how much he cares about you. Or you could have that perfect day where you and your friends ditch school and steal a Ferrari.

The other thing, maybe just as importantly, was that they took place, and were a lot of the times filmed in, my backyard, basically, in Chicago. That really meant a lot to me, and it made me connect with those films. You don't really get a lot of that with Chicago. You get Saul Bellow, but I was so young, I wasn't reading that yet. The Chicago connection was really important.

I feel like when you watch "Breakfast Club" you're forced to choose which one you are, and I realized I was definitely an Allison. — Jason Diamond

Do you think his portrayal of Chicago in the movies was accurate?

A lot of people talk about the lack of representation. I counted like eight black people throughout his movies in the '80s — one of them is a Michael Jordan cut-out. He doesn't really go out of his way to be like, "Hey, there's going to be some black people in these movies, and they're going to be part of the neighborhood or part of the school." And even as a kid, I noticed right away when I was 13, there were also no Jewish families. Ferris Bueller is played by a Jew, and his sister is played by a Jew, but he's not Jewish. And actually looking back on it, all of that is what it was like growing up in the part of the Chicagoland area I grew up in. I was one of three Jewish kids, maybe, in my school, and there were maybe two black kids and a few Latino kids. It was very white. So he does get that, and I think it's an unfortunate thing, because I think he could've really introduced this idea that everybody can live together; it doesn't have to be weird and separate like it is. So he unfortunately, I think, nailed that. But [his movies] look like Chicago. “Ferris Bueller’s Day Off,” I personally think it's his best movie, because it really does just nail Chicago so beautifully. And I know he really wanted to show the city he loved in a certain way, and I think he did a great job of that.

A big theme of the book is trying to do something and failing at it. Was it hard to write about that? I feel like it must be tempting for a lot of writers to gloss over those moments or to downplay them.

No. Honestly, I don't like holding things back. I remember watching basketball, and you'd see Dennis Rodman grab a rebound so fiercely, you'd get so pumped up, and he'd be like, "I play with a lot of emotion. You're going to see it all come out when I play." I kind of approach writing in that way. Not so much where I'm going to get a bunch of tattoos and write this really bad memoir called "Bad as I Wanna Be" or go to North Korea. But I always think of that. You can't really hold anything back. I'm not some swashbuckling Hemingway violent drunk, I don't [have] all these crazy, wild stories. But if I'm going to tell my story in any way, it has to be as honest as possible, and it has to give out the fact that I am a human and I am prone to a lot of failing. And if I didn't do that, A, the book would be crappy, and B, I'd be lying. I just don't want to do that.

Would you say that John Hughes had any influence on you as a writer?

I've thought about that a whole lot. I was asked that right as the book came out, and it was so hard for me to really say. I'm from the Midwest, so I'm kind of an "Aw, shucks" kind of guy at times. I do think that watching those movies so many times helped smooth out this sort of cynical distrust of the world and of culture that I might otherwise have from years of [bad] experiences. It definitely might have influenced the way I go about presenting things and telling stories, but as a writer, going back and reading his "National Lampoon" stuff, I'm like, "Hell, no, that didn't influence me at all." But the movies influenced me as a person, and as a person I'm a writer, so they kind of go hand-in-hand. Stylistically, no. The movie writer who has influenced is Nora Ephron. That's the person who I like to think about when I'm writing.

While you were writing the book, and even now, do you go back and re-watch Hughes’ movies?

Yeah, oh my God. After the book came out, not so much. There was one night when I was in Chicago on the book tour. It was after the book release, and I walked past this old movie theater, and they were showing "National Lampoon's Christmas Vacation" [which Hughes wrote and produced] and I was like, "How many times am I going to be able to say that I'm in my hometown, it's snowing out, and I just did my book release party, and I got a couple hours to kill, I'm going to see this movie." It was actually weirdly emotional to see Chevy Chase , which, you know, you should never get emotional about Chevy Chase. [Laughs.] I just watched "Home Alone 2." It was on in a bar the other night. "Pretty in Pink," I [recently] watched that.

"Home Alone 2" is severely underrated.

I don't know if you've ever looked this up online, but there's a lot of John Hughes movie theories. I have this theory that Kevin McCallister is the reincarnated H.H. Holmes, the notorious serial killer from Chicago, the "Devil in the White City" guy, because he just really likes torturing people in houses. There's something kind of dark about that to me. He's a creepy kid.

Are there any characters from the movies that you identify with particularly, or that you did as a kid?

I think the first one was definitely Molly Ringwald in "Pretty in Pink," because I just remember really being into the fact that she didn't care what anybody thought of her. She didn't let Steff get away with talking badly to her. I remember thinking, “I want to be that cool one day.” I'm still striving for that. I don't know if it'll ever happen. I feel like when you watch "Breakfast Club" you're forced to choose which one you are, and I realized I was definitely an Allison. I still feel that way. And Cameron. I also felt like Cameron [from “Ferris Bueller’s Day Off”] sometimes.

I identified with Cameron as a kid. I'm not sure why.

It’s weird, because we don't really see Cameron's parents. We don't get the full gist of what's so bad about them. We just see this really minimalist glass house in the forest. It's a beautiful house, by the way, in real life. But we don't really get to hear his back story, and we have an idea that it's bad, but we're not sure how bad. With John Bender [in “The Breakfast Club”], we know it's that bad. He's in a really bad situation. With Cameron, you really have to do a lot of thinking. He's a very cerebral character and I don't think we give him credit for that. He's so cerebral that there are Internet forums dedicated to talking about how Ferris Bueller is all in Cameron's head. It's like a Tyler Durden [from “Fight Club”] thing. He makes up Ferris and Sloane and the whole thing. It's pretty fascinating stuff.

People are still watching these movies. What do you think makes them, at least for some people, hold up so well?

I think everything eventually gets cool over time. You can say there's the teen aspect, because despite the fact that it looks outdated, the films still [reflect] the same kind of weird, emotional blender that kids put themselves through, when they're crushing on somebody, or having problems at home, or trying so hard that you're driven to depression. Those things still resonate. Things just mature. '60s garage rock was just a bunch of wild kids making music, and now a Sonics record is considered high art, and in the '60s it was just a bunch of kids making noise. Things seep into the canon, they make their way in, and it's hard to argue their importance after 30 years because they've influenced so many people and meant a lot to millions of folks throughout the world. You can go from [J.D.] Salinger to Judy Blume to John Hughes to a lot of young adult fiction we're seeing today, like Rainbow Rowell and John Green. He's in that canon of things that may have been aimed at teens, may have been about teens, but people grew up with it, and they're passing it down and carrying it on and finding new ways to tell those stories.

What do you think people in 2017, in this kind of fraught day and age we're in, what do you think we can learn from John Hughes' movies?

One thing, and this is important, is that things aren't always as great as they look. John Hughes painted this picture that everything's going to be OK, and everything's going to work out. And I like that, it's nice in a movie. But in real life, you've got to be constantly vigilant, because things don't always work out the way you want. You have to take it day by day. His movies aren't great epics, they take place in a day or two days, usually, and the characters in those movies really do take their lives day by day. In “Ferris Bueller” especially, [there’s] this idea that you can make your life a little better, and you can change things, and you can do what you want and be a little rebellious and it'll work out. I think it's important to remember those things. The kids that he's focusing on are just trying to get a date to the dance. You should take what you have the day it's there, and work with that.