We all have a mild obsession with the movies and TV shows we grew up with, the entertainment that helped shape who we’d become (types this writer after just crying his way through his first re-watching of 1992’s "A Muppet Christmas Carol" since Hanson was a thing). Very few of us, however, decide to channel that obsession into writing a biography, hunting down the creators and performers behind their childhood icons.

That’s exactly what Chicago-raised author Jason Diamond did with his book "Searching for John Hughes" – or at least what he attempted to do. With no experience and no real idea of how to write a biography, Diamond’s quest was long-lived but short on, well, an actual biography. But while the ’80s movie icon stayed far out of reach, Diamond discovered someone else – wait for it – himself.

Diamond will bring his failed Hughes biography but terrific pop culture-soaked personal memoir to Urban Harvest Brewing Company in Walker’s Point on Wednesday night at 7 p.m. – an event co-sponsored with Boswell Book Co. and OnMilwaukee.

Before he brings his book to Brew City, however, OnMilwaukee chatted with the author on what it was about the ’80s films that spoke to him, today’s nostalgia pop culture craze and his favorite John Hughes movie of the bunch. 

OnMilwaukee: What was it about John Hughes and his movies that really attracted you? Was it the Chicago connection or something deeper than that?

Jason Diamond: I was a little young when all his teen movies came out, so it kind of felt like I was being given a window into cool teen culture. I felt like I was cooler than my fellow 7-year-olds. But also, in the ’80s, all the movies that came before were like California or New York or somewhere that I wasn’t, and suddenly I was watching movies that were like right down the block from where I lived.

When did the moment strike you that you wanted to write a John Hughes biography, despite having no qualifications to do that?

When I was drunk. In true, surly, dumbass, Midwestern-guy fashion, it seemed like a good idea when I was drunk and trying to impress somebody from high school with what I was "doing" as a writer. It was something I’d been toying with mentally, but it just popped into my head to say that. But then it kind of stuck. I was like, "Maybe I should do that! Yeah, I could write a biography! DIY! Punk rock! I’m gonna do this!" And that’s just not how you go about doing that, and unfortunately, it took me five years to realize that.

When was the moment you realized this wasn’t going to happen?

It was a series of moments. Going to the middle of nowhere of Pennsylvania to find Michael Schoeffling, who played Jake Ryan, and not having that work out and going back to my $30-a-night motel room and having the roof cave in kind of felt like a sign. Missing John Hughes by, like, inches a few times.

Finally, when he died, that was it. I was like, "This is not happening." It was weirdly sobering. Five years later, I was like, "This was a silly idea." (laughs) But him dying really put the stamp on it.

What do you think it is about John Hughes movies that have lived on through generations? I mean, they’re such ’80s movies and products of their decade, but teens generations later still love and relate to them.

On one hand, I think people like that they’re neat little packages. They have happy endings. I’m kind of happy you don’t get happy endings all the time anymore; people like to leave things a little muddy or not give you the answer you’re looking for, and I appreciate that. It’s like a blanket; you know what you’re going to get, and that’s nice.

But I also think, and this is something I’ve noticed in the last decade, about how people have taken the films and put their own spin in it and evolved his work. I mean, the ’90s had some pretty good teen films, but I don’t really think they were that influenced by him, like "Clueless" and "10 Things I Hate About You." But then you started seeing "Mean Girls" and then last year "Dope" came out and this year with "Edge of Seventeen." I think the evolution of the teen film is something you can really thank him for, and that’s something I think brings people back to his movies and see where they started.

Nostalgia is a really big thing right now. How do you feel about that – especially as one who wrote about a major component of that craze?

I actually tweeted a photo a few months ago of Kyle MacLachlan and Laura Dern, and I went Twitter viral. It was retweeted like a thousand times or something. I had said, "This photo looks like it could’ve been taken in Brooklyn last night," and I remember Kurt Andersen from Spy Magazine retweeting it, being like, "That’s the problem with everything today. There’s nothing original, blah, blah, blah." And I’m like I wasn’t saying that; I was just saying it’s a cool thing that it looks so modern to me.

For me, growing up and going to high school in the ’90s, I was a weird kid. I liked ’80s hardcore and ’60s soul music and weird comic books, like R. Crumb comic books. And John Hughes movies, to me, fit into that canon because they were from a different era. My obsession with them, even as a teen, felt like something that was my own. And when you’re at that age, you’re looking for things that feel like yours. You’re looking for friends that feel like yours.

So seeing today rehashing nostalgia, it kind of does bother me a little bit, when it’s done in this kind of cheeky or cheap way. But like, "Stranger Things," I was really fascinated by how they did that. I appreciated that, and I appreciate when it’s done well. That’s why I think I like "Dope" so much, because it’s set in 2015, but it goes out of its way to reference ’90s hip-hop. That’s cool. That’s a little trick, I thought, and it really interested me.

Do you have a favorite John Hughes movie?

I don’t! People ask me that, and I honestly, really, truly could not pick one specific favorite. But I can say, out of all of them, "Ferris Bueller’s Day Off" is probably the one that I will go back to the most, because I feel it’s more philosophical than we give it credit for as a film. The idea of just having a perfect day, no matter what any douchebag adult authority figure is trying to stop you. You’re going to rally against that. You’re going to see a Cubs game – or a Brewers game if you’re in Milwaukee; Brewers games are fun as hell. You’re going to go hang out with your friends and do what you want and have that day.

Now, as an adult, I still watch the other movies and really love "The Breakfast Club" and the "Vacation" movies, but "Ferris" is still the one that resonates with me as a 30-something.

For a brief moment there, I thought you were going to say, "The one that really speaks to me is ‘Flubber.’"

That’s the one I always want to say just to f*ck with people! I don’t love "Flubber" because I had to watch it so many times when I was babysitting my little half-brother. But I’d go to bat for his remake of "Miracle on 34th Street." I think it’s a really dark movie. I think that’s a good one. Obviously, it’s not the classic, but I actually think it’s a lot darker than people remember it for, and I kind of appreciate that.