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Stevie Van Zandt is the ultimate underboss. His first big break came in the mid-70s as Bruce Springsteen’s right-hand man, guitarist, and occasional co-producer in the E Street Band. Later he seamlessly made the jump to acting as one of Tony Soprano’s key consiglieres, Sil, on The Sopranos.

Van Zandt recently released his memoir, Unrequited Infatuations, which details his career over the past 50 years.

On today’s episode Bruce Headlam talks to Van Zandt about the budding New Jersey rock n’ roll scene in the ‘60s, and what it was like recording with legendary R&B singers like Ronnie Spector and Darlene Love. He also reminisces about first meeting Springsteen—who Van Zandt says he saw go from a shy kid who was too timid to speak, to one of the greatest entertainers of our time.

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…