Sunday Sitdown with Willie Geist: Jelly Roll on His Journey from Struggle to Country Stardom

Podcast Date: August 31, 2025
Guest: Jelly Roll (Jason DeFord)
Host: Willie Geist

Episode Overview

Willie Geist sits down with Jelly Roll, the multi-talented musician whose real-life journey from a troubled youth, addiction, and incarceration to Grammy nominations and sold-out arenas has made him one of the most compelling figures in American music. The episode covers Jelly Roll’s surprising rise from an underdog in Nashville rap to a country music sensation, his ongoing advocacy work, personal struggles, redemption, and his mission to help others who’ve faced similar adversity.

Key Discussion Points & Insights

1. Jelly Roll's Meteoric Rise and Humility

• Recent Triumphs:
  • Jelly Roll had just played Madison Square Garden, headlined Central Park’s Global Citizen Festival, performed on SNL, and sold out multiple arenas.
  • Jelly Roll: “I would say I dreamed about it, but that’d be a lie. I just… wasn’t brave enough to dream this big.” (04:50)
• Staying Grounded:
  • He disconnects from his phone during big moments, focusing on being present.

2. The "Saturday Night Live" Moment

• Cultural Significance:
  • Jelly Roll describes performing on SNL as a dream he never dared to dream and a pivotal moment for his community:
    • “Especially, like, who I represent and the slice of America I speak for… we’re often not spoken for on platforms as big as Saturday Night Live.” (05:29)
• Being Vulnerable:
  • Noted how moving it was to make SNL's audience cry during a comedy show.
  • Emphasized importance of authenticity over chasing “highlight reels.”

3. Touring & Work Ethic

• Old-School Touring:
  • Prefers relentless touring—up to five nights a week—reflecting his roots playing for $50 gigs:
    • “You live that way for so long that when it’s time to keep doing it, you’re like, well, this is the way we like to do it.” (09:11)

4. Beautifully Broken: The New Album

• Themes and Intent:
  • The album is focused on redemption, hope, vulnerability, and mental health:
    • “I look at this as more of a diary into my mental health.” (11:17)
  • Aims to create honest dialogue about struggles, emphasizing, “Just because one's broken doesn’t mean they’re not beautiful.” (12:30)
• Community-Building:
  • Strives to shine a light on those not usually represented, especially in pop culture.

5. Advocacy & Giving Back

• From Problem to Solution:
  • Takes pride in “cleaning up” after his past; emphasizes accountability:
    • “I’ve been carrying a big broom around the last few years, and I still have a lot of work to do.” (16:15)
• Dinkins House Project:
  • Partners with a former prosecutor turned juvenile judge to create vocational opportunities for at-risk youth:
    • “I will hang drywall and cut a check. You tell me which one you need me to do, if not both.” (17:16)
• Financial Commitment:
  • Shares that he donates not just time and platform, but also significant personal funds to causes supporting those overcoming addiction and the formerly incarcerated.

6. Early Life, Music as Medicine

• Antioch, TN Upbringing:
  • Grew up in a diverse, working-class community.
  • Mother suffered from mental health issues; music was the family's emotional glue:
    • “I always used the expression, I would watch my house go from kind of dreary to a nightclub… music helped people.” (19:23)
• From Hip-Hop to Country:
  • Began in hip-hop due to Antioch’s diversity and the 90s scene—“the language of that community was hip hop.”
  • Eminem’s sampling of Jelly Roll (25:20) was a full-circle moment:
    • “The coolest call I could have got.” (24:31)

7. Redemption, Fatherhood, and Second Chances

• Youth Incarceration:
  • Jail time began at 14, with an adult charge at 16—“we were kids… but we were treated as if we weren’t.” (27:43)
  • Struggled to forgive himself until raising his own daughter helped him understand child development and regret.
• Becoming a Father:
  • Birth of his daughter, while in jail, gave Jelly Roll purpose and forced him to change:
    • “As soon as she was born… I was like, I can’t do this, man.” (29:47)

8. Building a Career from Nothing

• DIY Hustle:
  • Sold CDs and T-shirts on the street; used early YouTube to self-promote.
  • “My only skill set was music. So, for me, it was music or bust.” (31:05)
• Breaking Out:
  • Cites the song “Save Me” (34:38) as his tipping point, inspired by Malcolm Gladwell’s theory:
    • “Save Me was the beginning of the tide turning.”

9. Navigating Success & Staying Relatable

• Country Acceptance:
  • Embracing being labeled “country,” while always telling the same story, just “changing the furniture in the living room.” (36:18)
• Fame:
  • Views increased fame as a continuation of neighborhood recognition—now on a global scale:
    • “The world’s starting to feel more like Antioch.” (37:37)
• Impact on Stage:
  • Stage performance still feels most natural; wants his show to feel like “the night of your life at a bar,” or “the most intimate, honest moment you’ve ever had.” (53:58)

10. Major Awards and the Impact of His Message

• His Viral Acceptance Speech:
  • Unscripted, passionate, and faith-inspired. Views the platform as “church for people who traditionally don’t go to church.” (41:14)
• CMA Recognitions:
  • Nominated for Entertainer of the Year, Album of the Year, Male Artist of the Year—humbled, still feels out of place among country’s elite.
• The Sophomore Album Challenge:
  • “I hope that this album is to prove that I’m here to stay… I feel like people are watching, and they care what I have to say.” (45:32)

11. Perspective & Legacy

• Responsibility to Fans:
  • Sees himself as a voice for people not often reflected in mainstream music:
    • “I hope that when my people see me in a commercial or sitting on this couch, they’re like, that’s our guy… we’re being heard.” (47:46)
• Long-Term Outlook:
  • Open to telling stories in any future medium, but intent on following a path led by faith and purpose—family and community remain paramount.

Notable Quotes & Moments

• On Living the Dream:
  • “I wasn’t brave enough to dream this big.” (04:50, Jelly Roll)
• On SNL Representation:
  • “We’re often not spoken for on platforms as big as Saturday Night Live.” (05:29, Jelly Roll)
• On Redemption and Breaking Cycles:
  • “It started with… having extreme accountability and going, man, I helped make this mess. As my heart started getting right, I started feeling a responsibility to go clean it up.” (15:43, Jelly Roll)
• On Childhood and Music’s Power:
  • “I’d watch my house go from kind of dreary to a nightclub… music helped people.” (19:23, Jelly Roll)
• On Becoming a Father:
  • “I was the lowest common denominator… I was a crack dealer. And I was like, I can’t do this… I gotta figure this out.” (29:47, Jelly Roll)
• On the Tipping Point of His Career:
  • “Save Me was the beginning of the tide turning, where it was like, oh no.” (34:38, Jelly Roll)
• On Awards and Not Fitting In:
  • “I’m still dealing with the fact that I don’t feel fully fit in there yet. Not as a country guy.” (43:00, Jelly Roll)
• On Audience Connection:
  • “Most people just… hate Jelly. They’ll just be like, ‘what’s up, Jelly?’ And I’d be like, ‘what’s up, y’all?’ It’s really cool.” (37:37, Jelly Roll)
• On Stage Purpose:
  • “I would never charge to sing songs… it’s what I do, baby.” (53:54, Jelly Roll)
• On Responsibility as a Voice:
  • “I don’t feel pressure. I feel a great amount of gratitude.” (47:46, Jelly Roll)
• On Future and Calling:
  • “I’m here to tell stories and I’m just not sure what way I’ll be telling stories next year… I definitely want to take some time to spend with the family…” (49:36, Jelly Roll)

Highlighted Segments (with Timestamps)

• Jelly Roll reflects on recent breakout moments, SNL, and musical journey:
  04:15 – 06:09

• Redemption & mental health in ‘Beautifully Broken’:
  11:17 – 12:30

• Advocacy for youth and the Dinkins House Project:
  16:43 – 18:19

• The power of music in his family and early hip hop roots:
  19:23 – 23:27

• Eminem samples Jelly Roll: full circle moment:
  24:27 – 25:21

• Going from incarceration to music hustle:
  27:43 – 32:14

• Breakout hit ‘Save Me’ — career turning point:
  34:38 – 35:49

• Navigating new fame, stage presence, staying authentic:
  37:23 – 38:46

• Viral acceptance speech and viewing his show as church for the unchurched:
  41:05 – 42:31

• Discusses responsibility to community, future aspirations:
  47:46 – 49:36

• Elation at performing in New York City, from Webster Hall to Madison Square Garden:
  50:31 – 53:20

• On stage being his home and purpose:
  53:32 – 54:26

Final Thoughts

Jelly Roll’s candidness, humor, and humility make this conversation much more than a celebrity profile. Willie Geist deftly draws out the interconnected threads of Jelly Roll’s life—trauma, redemption, faith, community, and enduring optimism. The episode is a testament to the power of honesty in music and personal growth, making it an essential listen for anyone searching for hope, inspiration, or simply a mesmerizing story of beating the odds.