I Had a Real Career Until I Met Jay Kogen — Jonathan Shapiro

Jonathan Shapiro spent years as a successful attorney, working for the Justice Department and prosecuting organized crime. Then he met Jay Kogen — and somehow ended up writing television. Jonathan joins Jay for a funny and surprisingly personal conversation about leaving the law behind and building a 26-year career writing some of television’s biggest legal dramas, including The Practice, Goliath, The Blacklist, Mr. Mercedes, and The Undoing. They talk about the strange rules — or complete lack of rules — in show business, why great scripts never get made, what real courtroom experience taught Jonathan about writing television lawyers, and how a chance encounter with Jay helped convince him that maybe life didn’t always have to be vegetables when you could skip straight to dessert. But the conversation goes deeper than their careers. Jonathan opens up about getting older, losing people he loves, his journey to sobriety, using humor to keep people at a distance, and why genuine connection has become more important to him with age. It’s a conversation about law, writing, failure, friendship, mortality, and what happens when you finally admit: “Yeah… I’m a writer.”Subscribe to Don't Be Alone with Jay Kogen for more conversations with writers, comedians, actors, creators, and thought leaders exploring life, creativity, politics, and the human experience. Website: https://www.dontbealonewjk.com/ Instagram: https://www.instagram.com/dontbealonewithjaykogen/ https://www.instagram.com/jaykogen/ Tiktok: https://www.tiktok.com/@dont.be.alone.wit Substack: https://substack.com/@jaykogen Merch: https://shop.app/ Learn more about your ad choices. Visit megaphone.fm/adchoices