The Rabbit Room Podcast Network & Matt Conner
The Deepest Cut
A podcast about the movement from painful experiences to meaningful music. Part of the Rabbit Room podcast network. (Rabbitroom.com)
Author
The Rabbit Room Podcast Network & Matt Conner
Category
Podcast website
Latest episode
Dec 19, 2025
Where to listen?
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Episodes
Mac Powell: "It's a Shame" 19.12.2025 23:07
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...
Kristian Stanfill: "Come to Jesus" 05.12.2025 22:12
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...
Cindy Morgan: "Bows and Arrows" 07.11.2025 30:10
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 musi...
Jenny & Tyler: "How Long" 24.10.2025 25:59
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...
Matt Wheeler: "Worn Thin" 10.10.2025 26:23
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...
Greg Lafollette: "Psalm 88 (Darkness is my Closest Friend) 12.09.2025 27:53
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 pra...
Sanctus Real: "On The Mend" 29.08.2025 26:59
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...
Ellie Holcomb: "Red Sea Road " 15.08.2025 29:32
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. See omnystudio.com/listener for privacy inform...
Ben Shive: "Bright Sadness" 01.08.2025 30:52
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 t...
Jon Guerra: "Teach Us That One Song" 18.07.2025 29:37
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 mus...
Taylor Leonhardt: "Lights Gone Out" 20.06.2025 34:44
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 conversa...
Out of Eden: "Rolling Stone" 06.06.2025 32:18
In this episode of The Deepest Cut , Lisa Nicole and Danielle Torres of Out of Eden open up about their song Rolling Stone . They discuss the challenges of writing about family, balancing honesty with responsibility, and navigating the complexities of vulnerability in music. Plus, after nearly 20 years away, they reflect on their journey and what’s next for Out of Eden. See omnystudio.com/li...
J Lind: "Generous" 23.05.2025 24:08
On an ordinary day in Manhattan, J Lind found inspiration in the smallest moments—ultimately shaping his song Generous . In this episode of The Deepest Cut , J Lind shares how his experiences as a med student and hospice volunteer influence his songwriting. Join us for a conversation on finding beauty in the mundane and meaning in unexpected places. See omnystudio.com/listener for privacy in...
Jason Gray: "Worth Staying For" 09.05.2025 39:58
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. See omnystudio.com/listener...
Andrew Osenga: "Hold The Light" 25.04.2025 26:49
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. See omnystudio.com/li...
Sara Groves: "Deal Breaker" 28.03.2025 37:28
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, t...
Brandon Heath: "Scars" 14.03.2025 32:27
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 traum...
Caroline Cobb: "Death, You Terrible Thing" 27.02.2025 30:08
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 une...
Sidewalk Prophets: "I Believe It Now" 14.02.2025 30:08
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 episo...
Andrew Peterson: "The Rain Keeps Falling” 31.01.2025 33:03
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,...
Zach Winters: "When It Falls Apart" 11.09.2024 22:00
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...
John Tibbs: "After the Night" 04.09.2024 26:24
For singer-songwriter John Tibbs, the months entering into the global pandemic of 2020 brought about a two-year period in which Tibbs says he could not write—for a number of reasons he documents in our conversation here. After years as a full-time artist on the road 200+ days per year, it was a seismic shift and a downward spiral. In this episode, we talk about that hard season, and John introduce...
Wild Harbors: "Break My Heart" 28.08.2024 38:03
There are a hundred ways in which the process of writing, recording, and releasing a song can be messy, especially when it’s written from a point of pain or borne out of difficult circumstances. For the members of Wild Harbors, those issues could multiply many times over, given that they’re not only a great pop duo out of Nashville, but they’re also husband and wife. We’re thrilled to share one of...
Becca Jordan: "House of Wonder" 21.08.2024 23:37
Becca Jordan is a thoughtful singer-songwriter in Nashville whose songs bend close to the earth. They’re grounded and relatable even as they’re also lovely and resonant. And that place where her songs meet the listener is where she says she’s wrestling these days. On this episode of The Deepest Cut, we sat down with Becca to talk about a song born out of personal pain in a loving community and how...
Andy Gullahorn: "Grand Canyon" 14.08.2024 28:12
Andy Gullahorn is onto something when he says that songwriting is the fastest way for him to connect to his heart. As we have conversations with artists about music that rises out of vulnerable moments, we’re ultimately talking about mining what’s inside—what’s at work in the heart of the artist. In this episode of The Deepest Cut, Andy discussed a progression of songs written for the deeply felt...
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