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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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.

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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.

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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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.

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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This episode originally aired November 29, 2019.

This native of Wildwood Florida is known for her critically acclaimed albums, her XM radio show, and her frequent appearances at the Grand Ole Opry. She breaks down the early years of her career and persevering through difficult times to make art.

This episode originally aired on August 31, 2018.

The Tulsa troubadour describes his transition from hardcore music to folk, how to put on a compelling live show solo, and staying inspired even when the creative process is painful.

Our guest this week on The Working Songwriter hails from The Woodlands, Texas. Hayes Carll is a singer, songwriter, and storyteller whose sharp wit and plainspoken poetry first broke through with his 2002 debut, 'Flowers & Liquor.' That was followed by 2008's 'Trouble in Mind,' which delivered the hit "She Left Me for Jesus" and cemented his place among the genre's most distinctive voices. Carll has toured with artists like Old Crow Medicine Show, Todd Snider, and Alison Krauss and his songs have been covered by Miranda Lambert, Lee Ann Womack, and Kenny Chesney. He's recorded for Lost Highway, Dualtone, and Thirty Tigers and he's performed on stages from Newport Folk Festival to Austin City Limits and the Grand Ole Opry.

'Rolling Stone' praises his work for its "razor-sharp wit and lived-in warmth," while NPR notes his "keen eye for the human condition wrapped in disarming charm." 'American Songwriter' calls him "one of Americana's most reliable truth-tellers."

Our show's most frequent guest pops by to discuss his latest album "We're Only Human" and finding a creative voice that's more true to himself.

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