The Deepest Cut

Andrew Osenga spent nine years chasing the right words for a song that refused to be finished. From his days with The Normals to his time in Caedmon’s Call, the chorus lingered—waiting for the right moment. That moment came through deep personal loss, shaping Hold the Light into a powerful reflection on grief, community, and persistence in songwriting. 

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In a time of deep division, singer-songwriter Sara Groves reflects on the challenge of staying connected amidst anger and isolation. Inspired by the biblical plague of darkness—when “man could not see his brother”—she wrote Deal Breaker as a way to process both grief and hope. In this episode of The Deepest Cut, Sara discusses the shift ...

In this episode of The Deepest Cut, singer-songwriter Brandon Heath opens up about the heartbreak of the 2023 Covenant School tragedy in Nashville—a loss that hit close to home. He shares the story behind his song, "Scars" and how a songwriting session with some friends turned into a raw and vulnerable time of processing the grief, the pain, the anger, and confusion resulting from the traumat...

Caroline Cobb has been a singer-songwriter for over a decade and has more recently become an author with the release of her book Advent for Exiles. On this episode of the Deepest Cut, Cobb discusses the origins of her song “Death, You Terrible Thing,” reflecting on the loss of her father in the midst of a global pandemic and the way that both death and beauty arrived to meet her in unexpected ways.

And it’s that s...

Ben McDonald has been writing, recording, releasing, and performing songs about hope for nearly 25 years. Almost half of that time, he and his wife Carie were experiencing the very absence of it as they tried again and again unsuccessfully to have children. These days, the McDonalds are a family of three, but the shadows that loomed over so many years are still informing the present.

On this episode of The Deepest Cut, we sat down ...

In this episode of The Deepest Cut, Andrew Peterson reflects on the painful experiences that shaped his song "The Rain Keeps Falling." He shares the loneliness behind its creation and pushes back on what it means for art to be “honest,”—giving all of us a reason to think more about the ways that beauty invades the spaces we inhabit. Known for his work as an award-winning author, songwriter, filmmaker, and founder ...

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. 

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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...

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 conflic...

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...

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,...

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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