Jason Diamond Discusses Writing his Memoir and John Hughes’ Legacy

The author and Rolling Stone sports editor spoke at Politics and Prose about Hughes’ films and the writing process for his autobiography

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

One afternoon in New York City, Ally Sheedy walks into a bar and sits down at a table.

At an adjacent table, young, struggling writer Jason Diamond, is talking with a friend. He panics when he becomes aware of Sheedy’s presence. Diamond hopes that the actress, who played Allison Reynolds in filmmaker John Hughes’ 1985 movie The Breakfast Club, will speak with him.

Diamond sees some of himself in the character Sheedy portrayed in one of Hughes’ most popular films. At the time, Diamond is working on a Hughes biography and he hopes that Sheedy will provide him with insights to help him write his book. But first, he must get her attention.

Diamond silently mouths the words, “Call my phone,” to his friend, urging him to pose as Diamond’s agent. On the phone with his “agent,” he boasts about having recently interviewed a well-known actor. Little to Diamond’s knowledge, the celebrity he purportedly spoke with had recently passed away.

This anecdote is just one of many that Diamond, who is now 36, wove into his memoir, “Searching for John Hughes: Or Everything I Thought I Needed to Know about Life I Learned from Watching ‘80s Movies,” which was published on November 29, 2016.

The New York-based author and sports editor for Rolling Stone spoke at Politics and Prose on Friday, January 27 to promote his self-described “book about a book.” In a conversation with fiction author and essay writer Amber Sparks, Diamond discussed his experience writing his autobiography, his childhood, and what he considers Hughes’ best film.

Before Diamond spoke, Politics and Prose hosted a screening of Hughes’ 1986 comedy, “Ferris Bueller’s Day Off.” Diamond then read a passage from his memoir relating his encounter with Sheedy.

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.

A significant facet of Diamond’s memoir is his past failed quest to write a biography of Hughes. Diamond said his dream to write Hughes’ biography 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 explained. “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.”

Before he began writing his book, Diamond said that he had been thinking about failure and how adversity drives people to become who they are. He said he reflected on a time in his life when he had failed to achieve something. He thought of his failed efforts to write a Hughes biography, and that eventually turned into him writing a memoir.

“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.

Underscoring his optimism, Diamond noted, “I’m very hopeful. I mean, I’m a Chicago Cubs fan.”

Diamond spoke briefly about his childhood and his relationship with his family. He related that his parents put him on various medications when he was young to control his ADHD. Diamond shared 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.”

Diamond also discussed the movies Hughes made during 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 such as “101 Dalmatians,” “Flubber,” and “Home Alone.”

“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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