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.