• 39 minutes 50 seconds
    Mary Chapin Carpenter

    Our guest this week on the Working Songwriter hails from my neck of the woods, Washington, D.C. Mary Chapin Carpenter got her start in the proto-Americana music scene of 1970s and '80s D.C. She broke out of that local circuit with her signing to Columbia Records; her debut album went quadruple platinum.

    She’s toured with Emmylou Harris, Shawn Colvin, and Rosanne Cash, she’s won five GRAMMY Awards, two CMA Awards, and two Academy of Country Music Awards. Her song, “Shut Up and Kiss Me,” went to the top of the country radio charts. Chapin Carpenter has appeared on the Late Night with David Letterman and Rolling Stone calls her "one of the most grounded, sentient songwriters of her generation." NPR has said that she’s “a singular voice in country and folk” and the New York Times praises her “intelligent, literate songwriting with emotional depth.”

    Simply put, she’s an all-timer. I got a chance to catch up with her earlier this year and hear about her musical journey so far.


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    1 May 2026, 6:21 am
  • 54 minutes 17 seconds
    Classic Episode - John Craigie

    This episode was originally aired on August 14th, 2020.

    This troubadour based in Portland OR has carved out a national audience for his heartfelt, wry folk songs. He speaks about crafting his shows, keeping them fresh night to night, and recording albums in an unconventional way.

    24 April 2026, 6:32 am
  • 37 minutes 42 seconds
    Charles Kelley of Lady A

    Our guest on the Working Songwriter this week hails from Augusta, Georgia, but has made his professional bones in Music City, USA. Charles Kelley was one of the founding members of Lady Antebellum – now known as Lady A – and is one of the group’s principal songwriters. Their crossover hit, “Need You Now,” became one of the defining songs of the 2010s.

    Lady A have sold over 18 million albums, won 7 GRAMMY awards, and their songs have been streamed over 5 billion times. Along the way Charles has also released a pair of solo albums, including last year’s Songs for a New Moon. He’s recorded for Capitol Records Nashville and Big Machine and he’s toured with Luke Bryan, Tim McGraw, Keith Urban and many others. He’s also appeared on The Tonight Show and The Late Show with David Letterman.

    Rolling Stone has said that Lady A’s “vocal harmonies helped redefine country radio in the 2010s” and Billboard calls them “one of Nashville’s most successful songwriting teams.” I got a chance to catch up with Charles a few months ago to hear about his musical journey so far.

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    17 April 2026, 12:53 pm
  • 1 hour 1 minute
    Classic Episode - Courtney Marie Andrews

    This episode originally aired on November 30th, 2018.

    The acclaimed songwriter from Phoenix talks about touring as a backup musician, producing her own breakout album, and her love of the road.

    10 April 2026, 6:00 am
  • 46 minutes 38 seconds
    Ricky Montgomery

    Our guest this week on the Working Songwriter resides in Los Angeles, but spent many of his formative years in St. Louis, Missouri. Ricky Montgomery first built an audience on Vine in his early twenties before releasing his self-titled debut album in 2016. That bedroom pop album was a cult favorite until 2020, when several of its songs exploded on TikTok, leading to a deal with Warner Records.

    Montgomery's singles, “Line Without a Hook” and “Mr. Loverman,” are RIAA-certified platinum and, all told, his catalog has collected more than a billion streams worldwide. That grassroots support has led to headlining tours with stops at the Wiltern in Los Angeles, Iriving Plaza in New York City, and the Pageant in St. Louis, to name just a few.

    This interview was recorded nearly 18 months ago and has been delayed due to a snafu on my end, but I’m so glad we get to hear it now. I think you’ll very much enjoy hearing about Ricky’s musical journey through his own words.

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    3 April 2026, 7:34 am
  • 31 minutes 55 seconds
    Classic Episode: Lee Ann Womack

    This episode was originally aired on June 29th, 2018

    One of Nashville's favorite daughters, by way of Jacksonville Texas, discusses arriving for writing appointments with children in tow, finding song inspiration in everyday conversation, and dealing with the success of an international crossover hit.

    27 March 2026, 6:00 am
  • 54 minutes 24 seconds
    Fruition
    Our guests this week got their start busking on the streets of Portland, Oregon, but it wasn't long before their popularity pulled them onto the open road. Jay Cobb Anderson and Kellen Asebroek are pivotal and founding members of roots music band Fruition. They have toured with Greensky Bluegrass, the Infamous Stringdusters, Yonder Mountain String Band, and many others and have appeared at iconic festivals such as Telluride Bluegrass Festival, WinterWonderGrass, and the Northwest String Summit.

    Fruition's 2018 release, 'Watching It All Fall Apart,' debuted at #3 on the 'Billboard' Bluegrass Albums Chart. 'Billboard' said, "Fruition have matured into one of America's most compelling roots acts" while 'Rolling Stone Country' noted that, "The trio's harmonies are as tight as anything coming out of Nashville." 'No Depression' declared that they're "a band whose chemistry feels lived-in and wholly authentic."   I got a chance to catch up with them a while back to hear about their musical journey so far.

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    20 March 2026, 6:00 am
  • 54 minutes 2 seconds
    Classic Episode: Lydia Loveless

    This episode originally aired on December 29th, 2017.  The Ohio native discusses her passion for classic country, capturing the vitality of live performance on a record, and her habit of constantly collecting material for writing.

    13 March 2026, 6:00 am
  • 44 minutes 30 seconds
    Jason Boland

    Our guest today on the Working Songwriter hails from Oklahoma and is a foundational contributor to the uniquely American genre of Red Dirt music. Jason Boland released his first album, 'Pearl Snaps,' in 1998 and has been on the road ever since. Nightclub by nightclub, fan by fan, he's built a devoted national audience.

    He's toured with Turnpike Troubadours, Cross Canadian Ragweed, Reckless Kelly, and a host of others. He's recorded for Thirty Tigers and Top Hat Records. He's appeared at Stagecoach, Luck Reunion, and the MusicFest at Steamboat. 'Texas Monthly' called him "equal parts poet, rebel, and road warrior" and 'Rolling Stone' declared his sound "unpolished, unsparing, and deeply human."

    I got a chance a while back to catch up with Jason and hear about his musical journey so far.

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    6 March 2026, 7:00 am
  • 55 minutes 7 seconds
    Classic Episode: Heartless Bastards

    This episode originally aired on April 28th, 2017.  Erika Wennerstrom, the creative force behind Heartless Bastards, discusses growing up in Dayton Ohio, signing to Fat Possum Records, and her techniques for bringing a song to life.

    27 February 2026, 7:00 am
  • 34 minutes 28 seconds
    Yung Lan

    Our guest this week on the Working Songwriter originally hails from Virginia, but made his bones in the bustling hip-hop scene of Atlanta. Yung Lan began producing tracks on his laptop as a novice with no ties to the formal music business. Signing a modest publishing deal got him in the room with some hip hop luminaries, and he seized the opportunity. His first success came when one of his songs made it onto Fetty Wap's self-titled album, which went platinum. He has since gone on to work with Nicki Minaj, Lil Wayne, Kevin Gates, and many others.

    Yung Lan's work on Morgan Wallen's song "Cowgirls" won him a BMI Country Award. All told, his songs placed with different artists have amassed over 6 billion streams and he's contributed to 30 albums with RIAA certifications. I got a chance to catch up with Yung Lan a few months back to hear about his musical journey so far.

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    20 February 2026, 3:00 pm
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