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In 2022, at 75 years-old, Loudon Wainwright III released Lifetime Achievement—an aptly titled album from a songwriter whose debut came more than fifty years earlier.

Over the decades, Loudon has built a reputation for his confessional style, writing candidly about the struggles and absurdities of family life, failed relationships, and the scars of parental abandonment. While his subject matter can be heavy, he often balances it with wit and humor. You’ll hear that today when he performs “Fam Vac” and “Back in Your Town” from Lifetime Achievement.

In this conversation with Bruce Headlam, Loudon reflects on how he leaned into his upper-class upbringing when he first began performing professionally, what it was like collaborating with guitar virtuoso Richard Thompson in the 1980s, and the magical feeling of stepping on stage for the very first time.

You can hear a playlist of some of our favorite Loudon Wainwright III songs HERE.

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…

Leah Rose

Leah Rose is a senior producer and hosts episodes of Broken Record. A former music editor at XXL Magazine, she also served as an on-air personality for Eminem’s SiriusXM channel, Shade 45.…