On this episode of The Deepest Cut, producer and songwriter Ben Shive reflects on the story behind Bright Sadness, a poignant co-write with Jill Phillips from her 2021 album Deeper Into Love. Written in the wake of a diagnosis and personal crisis, the song became a way for Ben to hold grief and grace in the same breath. Ben shares how songwriting helps him give shape to sorrow, not as a place to process pain, but as the work that begins after. This is a conversation about paradox, precision, and the quiet strength of hope.

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In this episode of The Deepest Cut, singer-songwriter Jon Guerra unpacks the decade-long journey behind his moving track Teach Us That One Song. Reflecting on a faith that has evolved from childhood certainty to adult complexity, Jon shares how the song captures a spiritual snapshot shaped by doubt, suffering, and fatherhood. Join us as we explore the tension between growth and permanence in music and the story behind one of Jon’s most personal works.

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In this deeply honest episode of The Deepest Cut, singer-songwriter Taylor Leonhardt opens up about a faith crisis that shaped her hauntingly beautiful song, Lights Gone Out. Taylor shares how a friend’s bold advice to “murder someone in the chorus” helped her embrace vulnerability and truth in her songwriting. From navigating darkness to finding creative clarity, this conversation explores the power of authenticity in art. Join us as Taylor reflects on pain, growth, and the courage it takes to “go there.”

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