Podcast Summary: “Classic Music Saved Me with Struggle Jennings”
Podcast: takin' a walk (iHeartPodcasts)
Host: Buzz Knight (episode with guest host Lynne Hoffman)
Episode Date: August 16, 2025
Guest: Struggle Jennings
Episode Overview
In this deeply personal and emotional episode, Struggle Jennings, rapper and country artist (and grandson of Waylon Jennings and Jessi Colter), shares his journey of overcoming adversity, addiction, incarceration, and family tragedy, illustrating the redemptive, transformative power of music in his life. The conversation covers Struggle’s childhood in a musical household, his turn to hip-hop as he navigated hardship, the burdens and blessings of legacy, the impact of prison, his journey to self-accountability, the loss and recovery within his family, healing through creativity, brotherhood with Jelly Roll, and his hope to help others through music-themed recovery clinics.
Key Discussion Points & Insights
Childhood, Family, and Early Musical Influence
- Legacy and Upbringing
- Born into an “outlays and rock stars” legacy, Struggle was deeply influenced by his mother’s music and his grandfather, Waylon Jennings.
“Summertimes, I’d get to go out on tour with them—standing backstage, watching Waylon do his thing… I was automatically just so drawn to the emotion in music.” (04:44) - His mom eschewed “handouts” and raised him in tough neighborhoods.
“...as I was growing, hip hop... was blowing up. That’s what I really latched onto—the storytelling, hard times and heartbreak, same as country.” (05:24)
- Born into an “outlays and rock stars” legacy, Struggle was deeply influenced by his mother’s music and his grandfather, Waylon Jennings.
- Creative Sensitivity
- Struggle’s empathy and tendency to “soak up everything” led him to write poetry at a young age, often about others’ experiences. “One of the first poems I ever wrote was about abortion… I was always someone to soak up everything around me.” (07:26)
- Early emotional connection to music: “As long as I can remember, I can remember feeling the emotion from songs… I can pinpoint a time of my life to a song a lot of times, an emotion.” (08:21)
Hip-Hop, Hardship, and Blending Genres
- Environment Driving Art
- Rap and hip-hop reflected his lived experience amidst personal and neighborhood adversity.
“By the time I was 12, I was in a gang… rap is just what I latched onto. It’s what made me feel like I wasn’t alone.” (10:19)
- Rap and hip-hop reflected his lived experience amidst personal and neighborhood adversity.
- Dual Musical Roots
- Despite this, country and southern rock remained in his life, especially with his uncles/dad.
“Country music was always the backdrop… always ingrained in me. I found comfort in country a lot of times just because of the storytelling… both coincided to pave the path to me being one of the first artists to mix the two genres.” (11:58)
- Despite this, country and southern rock remained in his life, especially with his uncles/dad.
- Creative Surge
- Currently has “65 unreleased country songs,” written during a three-month sabbatical. (12:25)
Bearing the Jennings Legacy
- Unique Blessing and Challenge
- Didn’t initially realize Waylon’s fame; at school, faced stigma about his famous grandfather and family’s troubled public image.
“Growing up with him as my grandfather, I didn’t really, you know, he's pawpaw… until I got older, I didn’t realize, man, my pawpaw is like the man.” (12:52) - Later, resisted taking the “Jennings” name, fearing assumptions about privilege.
“There’s a lot that comes with that. Some people automatically assume you’ve had it easier… If anything, it made it 10 times harder.” (15:07) - Eventually adopted “Jennings” for visibility and at his family’s urging, becoming “Struggle Jennings.” (16:04)
- Didn’t initially realize Waylon’s fame; at school, faced stigma about his famous grandfather and family’s troubled public image.
Perseverance, Accountability, and Prison
- Refusing to Give Up
- Waylon’s rags-to-riches story demonstrated that a better life was possible and inspired Struggle's faith and perseverance.
“I never gave up. Seeing him at his prime … I got to see what was possible.” (17:08)
- Waylon’s rags-to-riches story demonstrated that a better life was possible and inspired Struggle's faith and perseverance.
- The Pivotal Moment of Change
- Prison was a turning point—realizing that his choices left his children vulnerable.
“I was instilled with a lot of irrational beliefs… Then when those gates shut, my kids became the biggest victims.” (22:10) - Accepting full responsibility for consequences:
“Everything that is happening to me and to the people I love is a direct result of a decision I made. You can’t really hide anymore.” (22:54) - Acute moments of pain: Teaching his small daughter to cook over a jail phone, hearing she wasn’t being cared for, learning of her trauma from afar.
“My five-year-old daughter… crying saying, daddy, we haven’t eaten. And I’m having to teach her from a jail phone how to make macaroni and cheese.” (23:12)
- Prison was a turning point—realizing that his choices left his children vulnerable.
- Transformation
- Determined to fix what he broke, he dedicated himself to self-improvement:
“I spent every day of my five years training—mind, body, soul, spirit. Stripping down all those layers and finding out why do I keep coming back? How can I stop this vicious cycle?” (25:00) - Embraced his authentic self, symbolized by wearing turquoise jewelry after years of masking his true tastes. (26:30)
- Determined to fix what he broke, he dedicated himself to self-improvement:
- Redemptive Philosophy
- Sees obstacles as opportunities and is “purpose-driven”:
“If we can take all the pain and all the tragedy and all the bad mistakes and do something great with that, inspire others… it wasn’t in vain.” (27:03)
- Sees obstacles as opportunities and is “purpose-driven”:
Healing Through Music & Service
- Music as Therapy
- Journaling, songwriting, then sharing those stories became vital to healing and focus.
“Every bit. That’s always been my go to… showing that transformation… watching the tens of thousands, hundred thousands of people gravitate towards that, and use my music to help them get through whatever they’re going through… that’s what’s kept me straight.” (32:56, 02:43 repeated) - The responsibility and gratitude of public testimony keep him on his path:
“When you have a purpose, when you feel like there’s purpose in what you do… I don’t look at ops, I look at obstacles as opportunities.” (33:25)
- Journaling, songwriting, then sharing those stories became vital to healing and focus.
- Trauma and Resilience
- Shares dark family secrets (e.g., learning the truth about his father’s death) as a way to help others know they’re not alone. (34:11)
- Details the struggle and ultimate triumph of his children—daughter overcoming trauma to go to college, another daughter thriving and achieving despite adversity.
“My daughter… she just called me this morning… she graduated with a 3.9 GPA honors… There it is possible to turn it all around. You just have to believe.” (37:36)
- Sound Sobriety: Musical Rehab
- Founds music-based rehabilitation clinics, Sound Sobriety, to help others process trauma through songwriting and creativity.
“The concept… is, for me, writing was my biggest avenue of release and therapy… when they graduate, they'll get a BMI number and be a registered songwriter… hopefully give them hope and a career.” (39:07)
- Founds music-based rehabilitation clinics, Sound Sobriety, to help others process trauma through songwriting and creativity.
Friendship and Support: The Jelly Roll Brotherhood
- A Bond Forged in Struggle
- Lifelong friendship and collaboration with Jelly Roll provides support and accountability.
“He’s my bestie. We met—I was fresh out of jail, raising two kids. He had just got out… and we just automatically clicked… going on 23 years of friendship.” (44:00) - Their journeys included mutual losses, time in jail, and rising together as artists.
“Having somebody you just always know is there for you, has been such a major part… I believe a lot of people make a lot worse decisions when they feel like they’re all alone.” (44:57) - Describes Jelly’s inspiration in showing him a legitimate living could be made through music, not crime.
- Accountability:
“He calls me out… he likes to give me my own medicine, you know. I gotta hear my own sermon sometimes.” (49:32)
- Lifelong friendship and collaboration with Jelly Roll provides support and accountability.
- Grand Ole Opry Milestone
- Emotional story of being surprised with an invitation to debut at the Grand Ole Opry by Jelly Roll:
“I see him coming across the room and I can tell that he’s upset… he was like, they’ve invited you to play the Grand Ole Opry… My Opry debut fell on the same day as my last day of parole… I walked out on that stage a free man.” (52:24)
- Emotional story of being surprised with an invitation to debut at the Grand Ole Opry by Jelly Roll:
Music’s Healing Power and Inspirations
- Conviction in Music’s Power
- “I think [music] is one of the most healing things ever… once I got that [pain] out on the paper, once I sang it… not only did I get a level of healing, but then being able to play it for them… is a whole nother [level].” (41:18)
- Influential Artists
- Huge range, including George Strait, Ed Sheeran, Ron Pope, Chris Stapleton, Tupac, and Waylon himself.
“There’s so many… everything from old country, 90’s country… Ed Sheeran… Ron Pope… Chris Stapleton… Tupac… I couldn’t pinpoint one artist.” (42:28)
- Huge range, including George Strait, Ed Sheeran, Ron Pope, Chris Stapleton, Tupac, and Waylon himself.
Notable Quotes & Memorable Moments
- On Empathy:
“I’ve always been like the person to soak up everything… super empathic.” (07:26, B) - On Adversity and Legacy:
“It makes it 10 times harder… they expect you to feel this, they say, oh, you’re not like your grandpa. Well, of course I’m not, I’m myself.” (15:07, B) - On Hitting Bottom:
“My five-year-old daughter at the time is crying saying, daddy, we haven’t eaten, and I’m having to teach her from a jail phone how to make macaroni and cheese…” (23:12, B) - On Redemption:
“The same way I messed all this up, I’m the only one that can fix it.” (24:17, B) - On Music and Healing:
“Telling that story through my music… that’s what’s kept me going. That’s what’s kept me straight. That’s what keeps me focused.” (32:56, B) - On Brotherhood:
“Having somebody you just always know is there for you… has been such a major part of it.” (44:57, B) - On Triumph:
“My Grand Ole Opry debut… fell on the same day as my last day of parole. I walked out on the stage… a free man.” (52:24, B)
Timestamps for Key Segments
- Struggle explains his musical upbringing & influence: 04:44–07:18
- Early songwriting as an empath: 07:26
- Rap and hip-hop draw: 10:04–12:00
- Country legacy and name adoption: 12:45–16:45
- Never giving up—the Waylon effect: 17:08–19:16
- Life-changing moment in prison, self-blame, accountability: 21:01–27:03
- The healing and driving power of music: 32:56–33:25
- Personal/family trauma and resilience: 34:11–37:36
- Founding Sound Sobriety, music-based rehab: 39:07
- On music’s scientifically-backed healing power: 41:18
- Support system with Jelly Roll: 44:00–48:56
- Grand Ole Opry story: 52:24
Tone & Closing Reflection
Throughout the conversation, Struggle Jennings is raw, earnest, and deeply reflective, forthright about accountability and pain, yet unwaveringly hopeful in the power of art and human connection. The discussion is grounded in humility, honesty, and a pragmatic yet spiritually-charged belief that anyone’s story can turn around—if met with the right music, support, and resolve.
Summary prepared for listeners interested in powerful music life stories, redemption, legacy, and the healing force of songwriting.