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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