The Sweetest Debut: Jason Diamond on John Hughes and How Writing Failure Led to Success

Welcome to the Sweetest Debut, a regular installment in which we reach out to debut (or near-debut, we’re flexible!) fiction, poetry and nonfiction authors working with presses of all sizes and find out about their pop culture diets, their writing habits, and their fan-fiction fantasies. 

Jason Diamond’s cultural memoir, Searching for John Hughes, describes a childhood obsession with the 80s filmmaker and a failed attempt to become his biographer. Jason used to be the literary editor right here at Flavorwire, and we’re thrilled to feature his answers to our questionnaire. 

What is your elevator pitch to folks in the industry describing your book?_dsc0292

At first I really wanted it to be a memoir about failure, sort of like Larry David trying to write a modern Dickensian tale about a 20-something screwing everything up while trying to write a book. Now I tell them it’s a book about a formerly sad teen who turns into a sad adult and who is obsessed with John Hughes films, punk rock, and literature.

What you tell your relatives it’s about?

I haven’t really told them much. I don’t really talk to them for reasons I guess you can read about in the book.

How long was this project marinating in a draft or in your head before it became a book deal?

That’s a funny question because at the heart of the book is the story of me failing to write a book for five years. I kinda dwelled on that for about eight more years after that, so I guess you could say over a decade. The finished book, this specific one, was a few months. I usually come up with an idea, pitch it, and if it’s rejected and I still want to do it I try and find a way to make it happen. In this case, a book, I was lucky a really great editor wanted it.

Name a canonical book you think is totally overrated.

Damn. That’s a tough question. I’m going to take the hard way to take the easy way out by saying I think every book that achieves a certain status within our culture earns that spot for a reason. Sometimes I don’t get that reason or agree with it, but I try not to think too hard about it. I guess I could say I’m not a huge fan of Updike’s Rabbit novels. Does that work?

What’s a book you’ve read more than two times?

More than a few. Jami Attenberg’s The Middlesteins, James Baldwin’s Go Tell It on the Mountain, Fitzgerald’s Gatsby, Saul Bellow’s The Adventures of Augie March, a couple of books by Edith Wharton, Toni Morrison’s Beloved, and I’ve read The Catcher in the Rye a handful of times trying to see why that book had such a huge impact on me and a bunch of other people when they were younger. I get it, but I still kinda don’t in some ways.

What’s book or other piece of art that influenced your writing for this particular project?

So I read a lot and I’d imagine various little influences subconsciously creep into my work. I’m sure something I read by Gogol here or some Didion essay there maybe told my brain to word something a certain way, but I honestly would never in my life say that I was even attempting to write like them since I couldn’t for a billion reasons. I will say that Nora Ephron is probably my biggest influence as a writer. I think I’m also really influenced by Craig Finn’s songwriting a great deal. And I’d be lying if I didn’t say the films of John Hughes.

What’s your favorite show to binge watch when you’re not writing?

I got really into You’re the Worst. It helped me look at depression in a different way. I also got into rewatching The X-Files since my wife had never seen it. She got me hooked on Buffy so I figured I could return the favor.

What’s the last movie you saw in theaters?

For some reason I don’t go to see movies as much these days and I need to change that. This year I saw Ghostbusters and the year before we went to see Hocus Pocus at BAM. That’s it. Next year I plan to see at least three films in the theatre. It’s just so expensive and I feel weird being around so many people in the dark.

Do you listen to music while you’re writing? If so, what kind? 

I can only really listen to music without vocals when I’m writing. Editing I can blast The Stooges or Slayer or whatever, but when I’m working it’s anything from Explosions in the Sky to Terry Riley’s In C. I find drone and repetition to be really calming to work to.

Do you prefer working at a desk, bed or couch?

Desk. I have to be sitting up in a chair. I think I can only work at some kind of desk or table situation for some reason.

Morning writing or late-night writing?

I wake up super early to start writing but I do it when the spirit moves me. Honestly depends.

Do you tend towards writing it all out in one big messy draft and then editing, or perfecting as you go (or something in between)?

My biggest rule is not to edit while I’m going. It screws me up big time.

How do you pay the bills, if not solely by your pen and your wit?

I’m an editor by day.

What is your trick to finding time to write your book while also doing the above? 

Just make sure you carve out X amount of hours or write X amount of words each day.

If you could write fanfiction about any pop culture character, real or imagined, who would it be (e.g. Rihanna or a character from Mad Men)?

Again, I feel like I’d have to say a John Hughes character here.

Care to give us a little of that fanfic?

I worry that me putting any of my fiction writing out there, fanfic or otherwise, would be the end of my writing career. It’s not very good, so I stick to the nonfiction.