Jason Diamond Talks About “Searching for John Hughes” at Politics & Prose

Author of “Searching for John Hughes,” Jason Diamond discussed his angst filled memoir with Amber Sparks at Politics & Prose on Friday.


Jason Diamond, Rolling Stone sports editor and author of, “Searching for John Hughes: Or Everything I Thought I Needed to Know about Life I learned from Watching ‘80s Movies,” is an angsty teen turned Brooklyn writer. Like many aspiring writers, Diamond worked in various industries to support his artiste lifestyle. For years he was a barista and even worked at a cupcake bakery. Diamond writes humorously about this part of his life, defining that time of his life as a unnamedpermanent curse.

Often self-proclaiming to be drunk or high, Diamond attributes much of his anxiety and depression to growing up in a broken home.

“I was the product of a divorce,” Diamond said.

His father was abusive and his mother eventually absent after his parents’ divorce.

On January 27, Diamond sat down with Amber Sparks at Politics & Prose to speak about his new memoir, “Searching for John Hughes” and the events that inspired it.

“‘Just let me be this ball of sadness,’” Diamond said, remembering thoughts from his youth. “‘I’m gonna go listen to the Smiths. Leave me alone.’”

Punk rock music was just one outlet for Diamond’s distress. The other was John Hughes movies, hence the title of his memoir.

“Those are the things that saved my life,” Diamond said.

Famous for cult favorites like Pretty in Pink and The Breakfast Club, John Hughes recreated the awkwardness, anxiety and beauty of the teen years. Even today, the mischievous character, Ferris from Ferris Bueller’s Day Off, appears in memes and GIFs all over the internet.

“Ferris still works for a lot of people,” Diamond said.

Diamond is not alone in relating to John Hughes movies, but Diamond said, having grown up in a Chicago suburb, Hughes’ Chicagoland settings had a special influence on him.

“That was my guidebook on how life was supposed to look,” Diamond said. “He did this great job at making it look like the city I love.”

Diamond said that when he moved to Brooklyn, he lacked all qualifications to fulfill his dream: writing John Hughes’ biography. All the same, Diamond was determined.

In a white button-down, Chicago Cubs baseball hat and wide-rimmed tortoise shell glasses —all complimented by a thick grown-out beard— Diamond shared an excerpt from his new book, taking his audience (giggling) back to his early days in Brooklyn.

After receiving his first freelance check Diamond went to a bar with his friend and fellow writer, Matt, to celebrate. As they were talking about Diamond’s John Hughes biography, they spotted Ally Sheedy, the actress who played the “basket case” in The Breakfast Club, at a neighboring table. Diamond said he had a huge crush on her as a kid.

“I was an Allison,” Diamond said.

To help get her attention, Matt called Diamond’s phone as a fake publishing agent, Phillip. On the pretend phone call, Diamond loudly—enough for Sheedy to hopefully hear— mentioned an interview he had set up with Paul Gleason. After hanging up, a stranger informed Diamond his interview was probably cancelled because Gleason died a few months ago. Mortified, Diamond made a quick getaway with his friend.

The embarrassing incident is just one example of Diamond’s setbacks while trying to write a biography about a man he never met. After abandoning the biography and struggling with his writing career, Diamond said he decided to write about failure.

Though the main subject changed from John Hughes to the author himself, Diamond said he wanted to keep a Hughes-ian angle: tragedy filled but with a happy ending.

And so, as he set out to write his memoir, Diamond said he thought to himself, ““I’m gonna put the rocky parts in there and then, just wrap it up nicely.’”

At the beginning of the talk, the author wrapped up the book in one sentence. “The quick sale is: It’s a book about a sad teen who turns into a sad adult,” Diamond said.

For all the obstacles he faced growing up and as an freelance writer, Diamond does not portray the “sad adult” he refers to. As in his writing, Diamond constantly makes witty remarks to lighten otherwise serious topics.

“I mean I’m a very hopeful… I’m a Chicago Cubs fan,” said Diamond referencing the Cubs’ famously poor performance pre-winning the 2016 World Series.

Diamond’s optimistic look extends to his writing. He said he tried to channel a Ferris Bueller spirit in “Searching for John Hughes.” Diamond said Ferris Bueller’s Day Off showcases an important lesson he learned from Hughes movies: to be more present.

“If you’re not going to pay attention, it’s going to move by you so fast,” Diamond said.

At the end of the author talk, an audience member asked Diamond if it was difficult to relive some of life’s harder moments to write the memoir. Diamond responded that, though he was not too bothered while writing, it often got to him after putting pen to paper.

“The weird thing about a memoir is that you’re tasked with turning all these weird and uncomfortable things that happened to you,—you’re tasked to turn that into a story,” Diamond said.

Some of those harder moments involve Diamond’s family. He said friends sometimes questioned his decision to publish the memoir for this reason. But Diamond said he is not very close with his family.

“This is my book, not their book,” Diamond said.

“Searching for John Hughes” is not about his family. Nor, despite Diamond’s original plan, is it about John Hughes. It is about Jason Diamond, who said he is still glowing from the accomplishment.

“Finally, I get to this point and I’m happy,” Diamond said. “I’m a writer.”


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Isabella is a journalism major, francophile and health nut who loves dark chocolate, Otis Redding and Spanish cured ham. She loves traveling and dinner conversations that last until the wee hours of the morning.

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