Mac Powell warned me ahead of time that he was fully prepared to cry.

It’s not uncommon for us to talk about emotional subjects here on the Deepest Cut. After all, our subject matter walks us through the formative process behind a song that the artist or band has labeled as the most painful or difficult song they’ve ever released. It’s par for the course.

But for Powell, the song he’s ready to discuss is quite the outlier for his catalog, whether as the longtime front man for the globally-known rock band Third Day or the last few years as a solo artist. That’s because Powell says he normally doesn’t turn to songwriting to be his therapy. For all of the songs in Powell’s incredible catalog—which includes 10 million albums sold, 4 Grammy Awards and over 30 No. 1 radio singles—and for all of the nights Powell was taking center stage, it’s amazing how he managed to stay out of the spotlight of his own handiwork.

“It’s a Shame”, however, was different and on this episode of the Deepest Cut, Powell says he’s prepared to discuss the song publicly for the first time. The song itself is an empathetic exercise for Powell to find perspective and healing within an alcoholic family system. As connective as the song can be, it’s surprising that Powell hasn’t tried to mine the terrain for more of what he might have to say from such tender spaces.

We appreciate Powell’s openness and honesty here, especially on a subject he so rarely explores. His candor and careful approach—one literally full of care—make this a conversation that’s likely to remain with the listener long after it’s over.

We hope you enjoy this episode with Mac Powell.

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Kristian Stanfill has spent the last two decades helping shape the sound of modern worship through Passion Music—leading songs that have echoed through stadiums, college campuses, and churches around the world. But his latest offering, “Come to Jesus,” doesn’t come from a mountaintop. It comes from the valley.

Instead, Come to Jesus is an honest reflection from Krisitan on sobriety, disillusionment, and the kind of healing that only comes after hitting bottom. In this interview on the Deepest Cut, he shares how, after years of trying to numb failure and fear with alcohol, he came to a breaking point in 2020 that sparked a journey of recovery. What emerged was a simple but urgent message: Jesus is better. He’s the way forward. He’s the only way out.

Kristian speaks of “Come to Jesus” as both testimony and sermon, a song forged from his own transformation and the hunger he sees in a new generation of worshipers. Whether leading from a stage or writing with others, his sings it with all the fervor of a heavenly invitation.

Here’s our interview with Kristian Stanfill, a conversation about redemption, freedom, and the power of telling your story—one honest line at a time.

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Cindy Morgan knows the power of a moment.

A shadow stretching across a summer meadow. A yellow dress. A question from a daughter growing up too fast. These are the kinds of scenes that stay with her—images that slowly turn into songs over months, even years.

That patience and attention to detail have defined her decades-long career. As one of the most celebrated songwriters in Christian music, Cindy has earned two GRAMMY nominations, 14 Dove Awards, and 21 No. 1 hits. She’s written for artists across genres—Amy Grant, Vince Gill, India.Arie, Rascal Flatts—and built a catalog known for its emotional depth and lyrical honesty.

In this conversation, Cindy shares the long, personal journey behind “Bows and Arrows,” a song she spent nearly a decade writing for her daughter. We talk about writing from life, writing with care, and what it means to tell the truth as a mother and an artist.

Here’s Cindy Morgan.

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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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