Jason Diamond Discusses Writing His Memoir and John Hughes’ Legacy

Author Jason Diamond (R) speaks with a guest at D.C. bookstore Politics and Prose on January 27, following a discussion about his memoir, Searching for John Hughes.


When he was growing up, Jason Diamond was a John Hughes cinephile living in a broken home in the suburbs of Chicago, IL. Now, Diamond is a New York-based author and the Rolling Stone sports editor whose Hughes-centered memoir, a self-described “book about a book,” was published on November 29, 2016.

The 36-year-old writer spoke at Politics and Prose on Friday, January 27, as part of his book tour promoting Searching for John Hughes: Or Everything I Thought I Needed to Know about Life I Learned from Watching ‘80s Movies.

In a conversation with fellow writer Amber Sparks, Diamond touched on his difficult childhood, his experience writing his autobiography, and what he considers Hughes’ best film.

Before Diamond spoke, Politics and Prose hosted a screening of Ferris Bueller’s Day Off, Hughes’ signature 1986 comedy, from 6 to 7 p.m. The screening set a lighthearted mood before the talk and was a fitting segue to a discussion about Diamond’s quixotic quest to write a biography about the director.

Prior to Sparks and Diamond’s conversation, Diamond thanked Politics and Prose, one of his “favorite indie bookstores in the country,” for inviting him to speak about his memoir. He then read a passage from his book.

The excerpt focused on an incident while Diamond was living in New York City, trying to make a career as a writer. One day while Diamond was talking with a friend in a bar, Breakfast Club actress Ally Sheedy walked in and sat down next to their table.

Diamond, who was alerted by his friend, panicked when he learned Sheedy was there. Diamond wrote that he saw some of himself in the character she played in Hughes’ 1985 film. Still working on a Hughes biography, he hoped that Sheedy, a star in one of Hughes’ most popular films, would help him with writing his book. What followed was a story about Diamond urging his roommate to call his phone and pretend he was his agent in order to impress her.

After the discussion got underway, Diamond spoke briefly about his childhood and the relationship he has with his family. He talked about how his parents put him on various medications when he was young to control his ADHD. Diamond said that he is “not that close” with his family.

“It got difficult when I started to think about writing a memoir,” Diamond said. “I wanted to tell my story, but I couldn’t move away from telling the truth.”

“Still, it’s not a book about my family,” Diamond continued. “It’s my book. With that said, I was considering writing about failure.”

A crucial focus of Diamond’s memoir is his quest to write a biography of Hughes. Diamond said this dream motivated him to move to New York City when he was in his early twenties.

“I think my dedication to writing the Hughes biography was two-fold,” Diamond said in an interview following the talk. “One, I’m just very stubborn. I don’t like to know when to say no to something.”

“But also, I think that when you’re in your twenties and living in a big city, and trying to become any sort of artist,” Diamond added, “you hold on to an idea so tightly because you really want that idea to work. That idea becomes part of your identity.”

“That’s what I think happened with my idea to write a Hughes biography,” Diamond continued. “I just didn’t want to give my idea up. It took me a long time to realize that, and for me to move forward, I had to give it up. I’m glad I did.”

Following the talk, Diamond explained that he had been “sort of obsessing over failure” and how adversity “drives us to become who we are.” Before he began writing his book, Diamond said that he reflected on a time in his life where he had failed to achieve something. He thought of his failed efforts to write a Hughes biography, a story that eventually turned into a memoir of his entire life.

Diamond said he felt that writing his memoir was an “intense and deeply-emotional experience.”

“Unless you write a memoir, you don’t realize how weird it is,” Diamond said. “You’re tasked with taking your life and turning it into a story. You know the path you’re going down, but you have to take that and write it.”

“It took a lot out of me, and I’m glad I recovered,” Diamond said.

Despite his past adversities and challenging experience writing his memoir, Diamond remains optimistic.

“I’m very hopeful,” Diamond said during the talk. “I mean, I’m a Chicago Cubs fan.”

While speaking at Politics and Prose, Diamond discussed the movies Hughes made over the course of his prolific career. Hughes directed several coming-of-age movies, including Ferris, The Breakfast Club, Pretty in Pink, and Sixteen Candles, and worked on big-budget comedies like 101 Dalmatians, Flubber, and Home Alone.

In an interview after the event, Diamond said that he began watching the director’s movies when he was 6 or 7 years old. One of his babysitters would bring “big VHS boxes” filled with some of Hughes’ films to his family’s house in suburban Chicago.

“I just fell in love with the characters,” Diamond said, “and the way they talked and looked. Also, I realized that these movies were being filmed in my backyard, and that just blew my mind. Even when I was seven, I realized Chicago was in a lot of movies.”

Though he does not have a favorite Hughes film, Diamond considers Ferris Bueller’s Day Off to be the director’s “most complete” movie, as well as the “ultimate Chicago movie.”

“With Ferris, [Hughes] knew exactly what he wanted, and a big part of that was wanting to make a great movie about Chicago,” Diamond said. “He succeeded in that, but he also succeeded in creating a kind of character that is still relatable. The kind of character that even a 13-year-old today wants to be like. It’s a good movie. It still holds up.”

Through all his experiences, Diamond said he learned to “not give up on anything.”

“You might have an idea for a story, and you might have the idea about how it’s supposed to look, but that may not be the way to do it,” Diamond said.

“Maybe an editor will show you a better way to present it, or maybe an editor will say ‘no’ to you,” Diamond continued. “Then you could try submitting that story to another publication.”

“Learning those little tricks,” Diamond added, “learning that nothing is set in stone, and that I could write how I wanted to write and find my voice, it took a long time.”

“All these things helped me get to that point,” Diamond said, “and I’m pretty happy about that because I think I’ve found my voice.”


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American University Journalism graduate, drummer, reporter, researcher, writer, third culture kid, Washington Wizards fan, and past Education Week and Agence France-Presse intern.

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