When a late-night medical emergency upended Jenny Somers’ world, fear and fragility became unexpected companions. Out of that darkness came “How Long,” a raw and prayerful song shaped by grief, healing, and the Psalms. In this episode of The Deepest Cut, the beloved folk/pop duo Jenny & Tyler open up about the story behind the song, the private ways they process pain through music, and how their art continues to trace the thin places between lament and hope.

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In this episode of The Deepest Cut, singer-songwriter Matt Wheeler reflects on the painful season that inspired his 2024 single Worn Thin. Known for crafting songs rooted in literature, Matt shares how personal trials led him to a “thin place”—a sacred space where God felt closer than ever. From health struggles to spiritual renewal, this conversation explores the intersection of suffering, transcendence, and the healing power of honest songwriting.

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On this episode of The Deepest Cut, Greg LaFollette shares the story behind Psalm 88 (Darkness is my Closest Friend)—a hauntingly honest song born from a season of deep pain. Rather than rushing toward resolution, Greg explores what it means to remain in lament, offering worship for those still in the valley. It’s a moving conversation about faith in the dark, the power of honest prayer, and creating space for sorrow in our spiritual lives.

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In this episode of The Deepest Cut, Chris Rohman of Sanctus Real opens up about the deeply personal story behind the band’s single On The Mend. After decades of making honest, faith-driven music, Chris reflects on recent struggles with mental health and how a season of panic attacks led to a powerful new song about breaking down—and slowly healing. It’s a candid conversation on vulnerability, longevity, and the ongoing journey of making music that truly matters.

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On this episode of The Deepest Cut, singer-songwriter Ellie Holcomb reflects on the story behind “Red Sea Road,” a song written during a season of profound sorrow. She shares how grief, faith, and community shaped the songwriting process, and we explore her journey as a solo artist, author, and mother navigating creativity in hard places.

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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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