Jason Diamond's unstable young life in Chicagoland split between divorced parents helped drive his obsession with the tragicomic movies of John Hughes, such as The Breakfast Club and Home Alone. When life eventually led Diamond to New York City in the pursuit of authoring a Hughes biography, his eventual book editor persuaded him to write his memoirs instead – focusing on the impact Hughes' movies had on the author. Today, Jason Diamond talks with Ana Maria Allessi about failure, Florida, Cubs fandom, and the book writing process.
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