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James Taylor’s voice sounds sweet and carefree. It’s a gift that hides the darker side to his lyrics and life. He and Malcolm Gladwell sat and uncovered some of the more troubling moments from his early life in this conversation. James also talks about it in his audio memoir, “Break Shot,” available now through Audible.

They also discuss the beach music scene of the Carolinas and the music that got James interested in music. Some of those tunes are represented on his new album, “American Standard.” Where James reworks classics of the great American songbook.

The Hosts

Rick Rubin

In addition to being a podcast host, Frederick Jay “Rick” Rubin is an American record producer and former co-president of Columbia Records. Along with Russell Simmons, he is the co-founder…

Malcolm Gladwell

Malcolm Gladwell is co-founder of Pushkin Industries and host of the hit podcast Revisionist History. He is a journalist, a speaker, and the author of several New York Times bestsellers including The Tipping…

Justin Richmond

Justin Richmond is producer and co-host of the music podcast Broken Record with writer Malcolm Gladwell, New York Times editor Bruce Headlam, and music producer—and Def Jam co-founder—Rick Rubin. Justin…

Bruce Headlam

Bruce Headlam is one of the co-creators of the music podcast Broken Record. He worked at The New York Times for 19 years, including two years running the 50-person Video…