Podcast Summary: The Bobby Bones Show

Episode: MORGAN: Struggle Jennings On Getting Shot, Surviving Prison, and Carrying a Legendary Name
Host: Morgan (Premiere Networks)
Guest: Struggle Jennings
Date: September 1, 2025

Main Theme / Overview

In this riveting episode, Morgan sits down with rapper, country artist, and legendary namesake Struggle Jennings. Together, they explore Struggle’s tumultuous yet inspiring life journey—from a chaotic and traumatic childhood through the dark chapters of gang involvement, addiction, being shot, and multiple stints in prison, to becoming a devoted father, community leader, and thriving independent musician. The conversation is raw, emotionally charged, and full of candid reflection, centering around themes of resilience, redemption, legacy, and the transformative power of taking ownership of one's story.

Key Discussion Points and Insights

1. Growing Up Jennings: Dual Realities and Early Struggles

• Struggle shares stories of “always being the new kid,” moving often with his young single mother (03:44), learning early how to make friends by bringing snacks.
• Explains his stage name: Given “Struggle” by a friend upon returning from jail, moving on from his less “digestible” street name, “Lil Killer”. “You gotta go by Struggle… I ain’t seen nobody go through the stuff you go through on a daily basis” (05:04).
• Discusses his extraordinary family tree—grandson of Waylon Jennings and Jessi Colter, son of a teenage mom, raised amidst both poverty and the wealth/fame of Nashville music royalty (07:19).
• Endured family trauma: An abusive stepfather, his dad’s murder (originally told as a suicide), and his mom’s deeply independent struggle to provide.

2. Sliding Into Crime, Addiction, and Survival

• Struggle openly explains being drawn into dealing and gang life from a young age, influenced by both street role models and proximity to privilege (11:26).
• Laments, “The only people that had the Cadillacs and Jaguars were the drug dealers. So I always gravitated toward that” (11:30).
• Admits there were times music was sidelined: “There was a time where I wanted to be Tony Montana… Tony Soprano, John Gotti… went through different periods, eras of struggle.” (14:03)

3. Near-Death Experiences and Prison

• Struggle recounts being shot twice: “I got into a shootout there [at Big Bad Breakfast], got hit in the shin. It actually ricocheted under the car and hit me” (19:43).
• Details a destructive cycle: periodic stints in jail, attempts at turning life around, relapse into crime—“I knew I was good at being bad” (20:59).

4. Fatherhood, Grief, and Hitting Rock Bottom

• Shares deeply personal accounts of the consequences his choices had on his children: While in prison, his ex-wife spiraled into addiction, his daughter had to make dinner for siblings, and eventually his children entered foster care and faced trauma (24:00).
• Moving story of accountability: “I had to really take full accountability for all of it… I left my wife out there without a husband, my mom without a son, my friends without their friend…” (25:12).
• Daughter Innocence, after surviving immense hardship, graduated with a 3.9 GPA—his proudest on-stage moment (25:01).

5. Rehabilitation, Transformation, and Choosing a New Path

• While incarcerated, Struggle immerses himself in self-betterment: “Parenting, finances, critical thinking, anti-violence programs… just trying to learn how to reel your anger in” (28:43).
• Highlights importance of active change: “Change happens when the reality of the outcome becomes scarier than the fear of change” (27:00).
• On returning, completely different: “I lost 120 pounds, rid myself of a lot of irrational thinking…” (26:45).

6. Vulnerability, Grieving, and Being a Dad

• Shares learning healthy grief: “I had to put my grieving on the back burner… I’ve learned that’s not always healthy… Gotta find your own time to grieve” (33:27).
• Reversal of toxic masculinity: “The older I get, the more I realize real men cry… We have emotions… You gotta allow yourself to feel those emotions.” (35:28)
• Talks about raising five children and two stepchildren, especially as a “girl dad”, imbuing resilience in each (39:06).

7. Legacy, Music, and Standing in His Own Light

• Explains pressure and pride of being “Jennings”: “I could never be Waylon Jennings, but I can do the hell out of Struggle Jennings.” (45:12)
• Waylon’s advice: “Don’t try to stand in my light… find your own light. Be yourself.” (46:18)

8. Staying Independent, Staying Real

• Shares candid industry insights: prefers indie path, releasing prodigious amounts of music: “13 or 14 albums out, 85 unreleased songs” (55:44).
• Collaborative projects, working with Brian Martin, Shooter Jennings, Brantley Gilbert, and venturing fully into both rap and country.
• On independent hustle: “I just like to still be able to go into Kroger and shop. My community loves me…” (59:48).

9. Community, Service, and the Message of Redemption

• Struggle is now the Director of Send Musicians to Prison—sharing music and testimony in jails nationwide.
• Central message: “Don’t let your past define you… Anything you’ve been through is leading you up to where you’re supposed to be. Don’t be afraid of those flames.” (61:00)

Notable Quotes & Memorable Moments

• On his stage name’s origin:
  “I don’t know if a parent's gonna let her kid buy a CD from ‘Lil Killer’ ... My friend said, ‘You oughta go by Struggle. I ain’t seen nobody go through what you go through.’”
  – Struggle Jennings (04:32)

• On living between two worlds:
  “When I was in West Nashville, I learned a lot of those irrational beliefs… that outlaw mentality… then I’d go to Whalen’s and see the Jag, the Cadillac, the maid, and the nanny.”
  – Struggle (11:26)

• On redemption:
  “I have no regrets in life… everything I went through brought me to exactly where I’m at, made me who I am.”
  – Struggle (12:11)

• On coping with pain:
  “Try to be too tough, you’ll find out how weak you really are.”
  – Struggle (35:28)

• On the impact of prison:
  “I had to really take accountability for all of it... I left them out there without a father…”
  – Struggle (25:12)

• On legacy:
  “Don’t try to stand in my light… find your own light… you may not be everybody’s cup of tea, but you’ll be somebody’s cup of coffee.”
  – Waylon Jennings (as recalled by Struggle, 46:18)

• On motivating others:
  “I wasn’t born ready. I had to go through all the shit I went through to get ready. When they purify gold, they put it in fire... Don’t be afraid of those flames.”
  – Struggle (61:00)

Timestamps for Major Segments

• [03:36] – Childhood, moving constantly, “learned how to make friends, bring snacks”
• [04:10] – The origin of the stage name “Struggle”
• [08:31] – Family trauma, father’s murder
• [11:26] – Growing up between “the two worlds”
• [13:13] – First drug dealing, getting into crime as a teen
• [15:50] – Being shot, living dangerously
• [24:00] – Impact of prison on family, daughter’s story
• [26:45] – Prison self-work, drug programs, transformation
• [33:27] – Grieving process, handling loss
• [39:06] – Fatherhood, raising daughters and sons
• [45:10] – Musical legacy, Waylon’s advice
• [55:44] – Releasing music, upcoming records, working with peers
• [61:00] – Redemption message, summary advice: “Don’t let your past define you”

Conclusion

This episode offers a powerful portrait of Struggle Jennings’ life: an unflinching reckoning with pain, loss, and the hazardous allure of outlaw living, transformed by accountability, tenderness, and an ever-present creative drive. The conversation will move anyone interested in stories of redemption, family legacy, and the complex realities behind musical success.

Recommended for:
Listeners who seek stories of overcoming adversity, music fans, those affected by addiction or incarceration, and anyone inspired by real-life redemption arcs.