In this episode of The Deepest Cut, Jason Gray opens up about Worth Staying For—one of the most intimate songs of his career—exploring themes of abandonment, divorce, and personal accountability. Jason shares how he’s learned to transform pain instead of transmit it, creating music that resonates with his listeners in profound ways.

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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 from Culture Care to Culture Wars, the pursuit of a “generative life,” and the role of art in bridging divides.

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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 traumatic event.

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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 striving toward beauty that informs her work, to provide creative moments that interrupt with hope, with perspective, with companionship.

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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 with McDonald, a founding member of Sidewalk Prophets, to hear more about “I Believe It Now,” a song born in the darker moments of waiting.

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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 of the Rabbit Room, Andrew’s insight offers a fresh perspective on how beauty emerges from hardship.

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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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