Inside a quiet writer’s room at BMG’s Nashville headquarters earlier this month, Struggle Jennings leaned back in his chair and reflected on the road that brought him here — one that’s been anything but conventional.
The grandson of country royalty Waylon Jennings and Jessi Colter has never tried to escape his family legacy. But he’s never tried to replicate it either. Instead, he’s spent the better part of his career reshaping what outlaw country can look and sound like in the modern era — blending country storytelling with hip-hop influence, redemption narratives with street-level honesty. Now, with the release of his new album Last Name, Jennings isn’t just acknowledging the weight of that heritage; he’s owning it.
And in classic outlaw fashion, he’s doing it entirely on his own terms.
“This album is just really about redemption,” Jennings told Celeb Secrets during our intimate conversation. “It’s about the idea that regardless where you’re at in life, if you just keep pushing… anything is possible.”
When Jennings disappeared from the road for much of the last year, it wasn’t because the music stopped flowing. In fact, it was the opposite. He went into a period of relentless creation. Some of those projects include rap releases, collaborative albums, and music for artists on his independent label Angels & Outlaws. But Last Name sits at the emotional center of that creative explosion.
“I wrote about 250 songs,” he revealed. “I recorded and produced almost 10 albums in the last year and a half.”
The record — released March 13 via Angels & Outlaws/ONErpm — digs deep into themes of legacy, identity, redemption and survival. Across its tracklist, Jennings reflects on everything from the burdens of his surname to the personal transformation that’s shaped his life in recent years.
For the first time, he also took a step that pushed him far outside his comfort zone: hiring a vocal coach.
“I’ve been a rapper my whole life — world-class singer in the shower and the truck,” he joked. “But for the first time on this album, I really dug in and tried to find my voice.”
The growth, he says, is undeniable.
“If you listen to Monte Carlo and then El Camino and then this one, you’re going to hear the vocals grow so much. I really stepped up.”
For Jennings, Last Name isn’t just an album title but the central theme of the project. Being part of one of country music’s most legendary families comes with expectations, comparisons and an inevitable question: what does that name mean today?
Instead of running from it, Jennings leaned into it.
“I’m releasing the country albums for myself,” he said. “Because that’s what I love and that’s where I’m at.”
That doesn’t mean abandoning the genre-blending style that built his fanbase in the first place. Jennings was among the earliest artists to fuse country with rap long before it became a widely accepted crossover sound. While the industry once resisted that approach, today it’s become part of the genre’s evolving identity.
“We were kind of ahead of our time,” he said. “They shunned us for it for 20 years… but everything’s timing.”
That perspective shaped a creative decision that perfectly reflects Jennings’ dual musical identity.
“For every country album I release, I’m releasing a rap album right behind it,” he explained. “Because I owe it to the fans that brought me here.”
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Few moments in Jennings’ life capture the emotional core of Last Name more clearly than his debut at the Grand Ole Opry last June. To the audience, it looked like another triumphant milestone for a rising outlaw voice in country music. But behind the scenes, it carried far deeper meaning. The performance happened on Jennings’ final day of parole — ending a chapter that included prison time and years of rebuilding his life.
“Walking out on that stage… it was like a wink from God saying this is the end of one chapter and the beginning of another,” he said.
His children watched from backstage — a moment that made the journey feel full circle.
“It made everything that happened before that day not in vain,” he reflected. “My kids had been through so much… watching me go away, losing their mother, everything. For them to see me walk out on that stage — that meant everything.”
That kind of emotional honesty bleeds throughout Last Name.
Songs like “Garden of Stones,” “Storm I Can’t Weather,” and the title track feel less like polished radio singles and more like confessions set to music. The album also reunites Jennings with longtime collaborator Jelly Roll on the track “Only God Knows,” continuing a creative partnership that helped shape both artists’ careers. Jennings speaks about their friendship with nothing but pride.
“We had one hell of a run,” he said. “We came up together.”
While the two artists now travel very different paths professionally, Jennings says the bond remains.
“I’m beyond proud of him.”
Jennings’ upcoming tour reflects the same back-to-basics philosophy that fueled Last Name. Instead of massive productions and luxury tour buses, he’s scaling things down — hitting the road with a small crew, a DJ and a handful of musicians.
“Just a handful of us in a van,” he said with a grin.
The goal isn’t spectacle. It’s connection. It’s a sentiment that mirrors his broader philosophy about longevity in music — one rooted in authenticity rather than chasing algorithms.
“I spent last year creating the music… this year I want to create relationships with the fans again,” Jennings shared.
“To be timeless, you can’t worry about time,” he continued, recalling advice from a fellow artist. “I’d rather have a slower climb but a longer sustain.”
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Ultimately, Last Name feels less like a career checkpoint and more like a statement of purpose. For Jennings, the album isn’t about proving he belongs in country music or measuring up to the legacy of his family. It’s about carving his own space within it.
“This album is probably my favorite one I’ve made,” he admitted. “It’s really true to who I am.”
And that honesty — raw, imperfect and deeply human — is exactly what the outlaw tradition has always been about.
If Waylon Jennings helped define the rebellious spirit of country music decades ago, Struggle Jennings is proving that spirit still has plenty left to say.
Just don’t expect him to follow anyone else’s rules while doing it.
Take a listen to Late Name below and don’t forget to let us know if you’re loving the album by either leaving a reaction at the bottom of the post or by sliding into our DMs on Instagram at @celebsecretscountry.
