STRUGGLE JENNINGS – MAY 12, 2026 – THE WHISKY
On May 12th, Struggle Jennings graced the Whisky a Go Go with a set that was 50% concert, 50% sermon, and 100% life-changing. The latest stop on his “Last Name” tour, the show was a celebration of resilience and an ode to empathy, given an iron backbone by DJ Scatteredbrains, drummer Kareem Thompson and guitarist Sam Whetzel. From the first minute, in which DJ Scatteredbrains proclaimed “we’re all family here,” it was clear that this was an artist deeply attuned to his fanbase. That proclamation was only validated as the night pushed on and Struggle himself went above and beyond to make sure his fans knew how appreciated they were. Not only did he shake the hands of everyone in the front row who offered without missing a beat, he listened to their stories, praised their strength, and most importantly, gave them one hell of a show.
Struggle Jennings
Struggle Jennings
As his own last name suggests, Struggle is the grandson of Waylon Jennings, and thus the latest branch in one of his genre’s mightiest dynasties. But don’t get it twisted: Struggle’s music, a vibrant blend of country and hip-hop, is entirely his own. One’s first instinct might be to say “this ain’t your granddad’s country music,” but Struggle was quick to dispel that notion as well. Early on, he recalled old-school purists who told him that Waylon Jennings would be “turning in his grave” listening to his songs. “What they don’t know,” Struggle continued, wistful and good-humored, “is that Waylon used to love to hear me rap.” With that, he launched into “Last Name,” the title track of his latest album and one of the night’s highlights. The song is an ode to the men who raised him, and his own experiences treading in their footsteps.
“I never told my daddy goodbye,” he sang, “but the man in the mirror has his eyes.” With that, he took off his sunglasses and gave us a good look.
Struggle Jennings and band performing at the world famous Whisky a Go Go on May 12, 2026.
Struggle Jennings
“People don’t listen to Struggle Jennings unless they’ve been through some real shit,” he said, and it isn’t hard to see why. His lyrics, informed by his own hardships – losing his father to murder, a period of incarceration – give a voice to people who desperately need one. And what a voice it is: tender, booming, full of the love that only those who have truly known pain can muster. While introducing “Praying for Rain,” a heartbreaking ballad about a creek he used to visit with his father, both now long-gone, he implored the audience to bear with him: “Some of these songs are just as hard to sing as they were to write.” He did not falter on a single note, but the tears in his eyes shone bright beneath the Whisky’s lights.
But as breathtaking and powerful as such moments were, the night wasn’t all maudlin introspection. Far from it. From the appropriately-named opener “Howl At The Moon,” to the bluegrass-influenced toe-tapper “Before I Go,” Struggle and his bandmates proved to be just as adept at having straight-up fun as they are at soul-searing introspection. Speaking of which, another of the night’s biggest highlights came at the show’s midway point, in which an a capella rap session from Struggle segued into his hip-hop magnum opus, “Alligator Boots,” an undeniable refutation to anyone who still dares suggest that rap and country cannot coexist.
Struggle Jennings
While introducing “Garden of Stones,” another soulful epic that understandably got peoples’ hands in the air, Struggle related his process: “I don’t try to write a hit song, I try to write a song that hits.” That authenticity radiated through each and every performance, and is perhaps the key to his magnetic appeal. One of his most moving speeches in a night full of them came when he told his adoring fans that record labels aren’t for him, and there is nowhere he’d rather be than here with them. In the mouth of so many other artists, such a claim might feel dishonest. Not so with Struggle Jennings. He meant every word, and that honesty is why his songs hit.
DJ Scatteredbrains
Sam Whetzel
Kareem Thompson
As the night wound down, Struggle related yet more tales of he and his family’s incredible resilience. One of his teenage daughters, despite (or perhaps because of) immense childhood hardships, is founding an organization to help children who are aging out of foster care. Another of his daughters is about to have a child, an event which Struggle told us he would be flying back home to witness: the grandson of Waylon Jennings, about to become a grandfather himself. His final message to the fans to whom he has given such hope (and, no less important, such phenomenal music), was this: “It’s never too late. Wake up tomorrow and write the best f’ing chapter of your life.” The story of the night, and of this artist as a whole, is one of perseverance, the hard-won but necessary victories of those who have made mistakes but gone on to spin gold out of their struggle.
Struggle Jennings
Struggle Jennings
Review by Joaquin Waters
Photos by Scott Waters
Struggle Jennings
Whisky a Go Go
