Singer-songwriter Zach Winters says the most difficult song from his newest album, Shade of Indigo, is “When it Falls Apart,” a song that took considerable time to finish because he knew he had to thread the needle carefully when figuring out what to say. It’s a song that carries the grief of a friend and even offers up a response, and with that comes a very real responsibility to offer something substantive. 

If you’re familiar with Zach’s music, you know this isn’t much of a problem. Zach is a gifted poet and wordsmith whose compositions feel like the sort of cinematic melodies in which you can truly lose yourself. They’re thoughtful and beautiful and this song is no exception, a gift offered in grace to someone mired in grief.

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For singer-songwriter John Tibbs, the months entering into the global pandemic of 2020 brought about a two-year period in which Tibbs says he could not write—for a number of reasons he documents in our conversation here. After years as a full-time artist on the road 200+ days per year, it was a seismic shift and a downward spiral.

In this episode, we talk about that hard season, and John introduces us to his song "After the Night."

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There are a hundred ways in which the process of writing, recording, and releasing a song can be messy, especially when it’s written from a point of pain or borne out of difficult circumstances. For the members of Wild Harbors, those issues could multiply many times over, given that they’re not only a great pop duo out of Nashville, but they’re also husband and wife.

We’re thrilled to share one of the firstfruits from a forthcoming new album entitled “Break My Heart,” a song that came to Wild Harbors in a dry spell and admits the shadow side of loving something—that to love something is to also inevitably get hurt by the loss of it.

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Becca Jordan is a thoughtful singer-songwriter in Nashville whose songs bend close to the earth. They’re grounded and relatable even as they’re also lovely and resonant. And that place where her songs meet the listener is where she says she’s wrestling these days.

On this episode of The Deepest Cut, we sat down with Becca to talk about a song born out of personal pain in a loving community and how it’s a good example of the conflict she feels when presenting a song for anyone to hear. 

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Andy Gullahorn is onto something when he says that songwriting is the fastest way for him to connect to his heart. As we have conversations with artists about music that rises out of vulnerable moments, we’re ultimately talking about mining what’s inside—what’s at work in the heart of the artist. 

In this episode of The Deepest Cut, Andy discussed a progression of songs written for the deeply felt pain of a close friend and a house with an empty nursery where twins were supposed to be. It’s a conversation about mining the depths of the heart and bleeding responsibly for the sake of the audience. 

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Despite its sparse arrangements, there’s something so striking about Cecily's EP Love Letters and her clear God-given talents and the heart behind her work. 

Enjoy this conversation with Cecily as she walks us through the backstory behing the song "For a Little While."

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For singer-songwriter Zane Vickery, nothing remains hidden from view—no matter how deep the wound. For Vickery, the more he can convey the reality of his own experiences and emotions (including the darker shades involving pain, sorrow, and frustration), the greater the possibility of reaching someone in a similar place.

In this episode, Vickery talks about his views on vulnerability in songwriting and how they played into his song, “Whatever Light We Have.”

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For singer-songwriter Carolyn Arends, the one song she says was the most difficult to write and release was written as her community supported her as she struggled to grieve the loss of her mother. In her darkest moment, the mentors and those around her helped her find the right words for a way forward.

On this episode of The Deepest Cut, Carolyn talks about the origins of her song “To Cry For You.”

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Sho Baraka takes us inside "Words, 2006" and tells us what its release has meant for him and so many others who feel seen by its subject matter. In addition, Sho also shares about the juvenile state of hip-hop and what it means to pursue eldership within it. 

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For over 20 years, Jill Phillips’ catalog has served as a deep well from which others have drawn much-needed perspective, encouragement, and healing. Join Matt Conner as he talks with Jill about curiosity over shame, self-kindness, and how she “ugly cried” once when performing the song "If You Were Here." 

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