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Amanda Shires is a Texas-born singer/songwriter who got her start at 15 when she joined Bob Wills & His Texas Playboys on fiddle. After starting her solo career in 2005, Shires continued to play with a number of other bands including her husband Jason Isbell’s band, the 400 Unit. In 2019, she started the all-female country supergroup The Highwomen, which includes Brandi Carlile, Natalie Hemby and Maren Morris.

After the 2022 release of Amanda Shires’ seventh solo album, Take It Like A Man, she released an album of covers with the late Bobbie Nelson—who’s primarily known for playing piano in her younger brother Willie Nelson’s band. Amanda initially enlisted Bobbie to play on her version of Willie’s classic, “You Were Always On My Mind,” but they continued to record together. The resulting collection of songs became the album Loving You, which was released this past June, nearly a year after Bobbie’s death.

On today’s episode Justin Richmond talks to Amanda Shires about Bobbie Nelson’s unfortunate start in the music business. Amanda also talks about why she feels more comfortable singing about society’s big issues alongside The Highwomen. And she remembers the time she went to Vegas and gambled away all her band’s tour money—only to win it all back after playing craps through the night.

You can hear a playlist of some of our favorite Amanda Shires 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…