Mtp.Sad news: 30 minutes ago in Nashville, the family of 45-year-old Struggle Jennings, Jelly Roll’s best friend, suddenly announced that he had passed away…

Heartbreak in the Heartland: Outlaw Rapper Struggle Jennings, Waylon’s Grandson and Jelly Roll’s Ride-or-Die, Dead at 45 – A Sudden Loss That Shakes Nashville’s Underground Soul

Rolling Stone – November 30, 2025

NASHVILLE – The neon-lit streets of West Nashville, where the Nations neighborhood birthed legends from the shadows, fell eerily silent just 30 minutes ago. William “Struggle” Jennings, the 45-year-old outlaw rapper whose gravel-throated anthems of redemption and rebellion echoed the unfiltered spirit of his grandfather Waylon Jennings, has passed away. The news, delivered in a raw, tear-streaked family statement on his official social channels, hit like a back-alley ambush: sudden, senseless, and shattering a brotherhood that spanned prison yards, tour buses, and the unforgiving climb from street corners to sold-out stages.

“With hearts heavier than a Nashville downpour, we announce the passing of our beloved Struggle Jennings,” read the post, timestamped 8:15 p.m. CT from his family’s account. “He fought every battle with fire in his soul, turning pain into poetry that lifted us all. Gone too soon at 45, but his voice will roar forever. Services pending. In lieu of flowers, crank up ‘Outlaw Shit’ and raise a glass to the man who never broke.” No cause of death was disclosed—only a haunting photo of Struggle mid-verse, tattooed arms flexed around a microphone, eyes locked on some distant horizon only he could see. Within minutes, the post amassed 2.7 million views, a digital wake where fans poured out grief in waves: “Struggle was the soundtrack to my comeback,” one wrote. “Heaven just got a new rebel yell.”

Born William Curtis Harness Jr. on May 31, 1980, in the cradle of country royalty—grandson to Waylon Jennings and Jessi Colter, nephew to Shooter Jennings—Struggle’s path veered hard from the spotlight’s glow. Raised in the gritty underbelly of West Nashville after his father’s murder when he was just 10, he traded silver spoons for street survival, slinging mixtapes from his car trunk alongside Wyteboy Slim as early as 2003’s Strugglin’ Til We Make It. Prison stints in the mid-2010s forged his edge sharper, emerging in 2016 with the Return of the Outlaw EP on Yelawolf’s Slumerican label—a raw fusion of trap beats, country twang, and unflinching truths that caught fire in the underground.

But it was his bond with Jelly Roll—real name Jason DeFord, the tattooed troubadour who’s risen from felon to multiplatinum savior—that turned Struggle into a folk hero for the forgotten. The duo’s Waylon & Willie trilogy (2017–2018), a gritty homage to Waylon and Willie Nelson, blended hip-hop grit with honky-tonk heart, dropping bangers like “Outlaw Shit” and “Devil Is a Woman” that racked millions of streams and packed dives from Antioch to Austin. “Struggle was my brother in the trenches,” Jelly Roll posted moments after the announcement, a black-and-white selfie of them mid-laugh on a smoke-filled bus, captioned simply: “You pulled me from the fire, man. Now who’s gonna keep me straight? RIP to the realest. Love you eternal.” The message, laced with a voice note of their last studio jam—”a track we never finished, about outrunning the ghosts”—left followers sobbing in comment threads, one viral clip hitting 1.2 million plays as fans harmonized the hook: “We came from nothin’, built it from the dirt.”

Struggle’s solo run was a testament to tenacity. I Am Struggle (2013) and The Outlaw’s Prayer (2025) charted his metamorphosis—from dealer to dad, addict to advocate—while collabs with his daughter Brianna Harness on 2019’s Sunny Days (No. 3 on Billboard Blues) wove family threads into his rebel tapestry. He headlined the Grand Ole Opry in 2024, a full-circle nod to his Jennings blood, crooning “Twisted” under the hallowed circle: “Might’ve changed my ways but I never switched up.” Fans there recall him choking up mid-set, dedicating it to “the streets that raised me and the blood that saved me.” His Angels & Outlaws label mentored rising outcasts like Caitlynne Curtis, turning his ranch outside Nashville into a haven for wayward artists chasing the same haunted high.

The outpouring has been biblical. Shooter Jennings, Struggle’s uncle and only a year his senior, shared a childhood Polaroid on Instagram: two kids in overalls, mid-wrestle on Waylon’s tour bus. “You were the firecracker in the family fuse, lil’ bro. Grandpa’s proud—hell, he’s probably already booking you for the cosmic stage.” Yelawolf posted a Slumerican family portrait: “From the yard to the yard—Struggle, you outhustled us all.” Even Jelly Roll’s wife, Bunnie Xo, who co-hosted their podcast Dumb Blonde, broke her usual armor: “He was the uncle my kids needed, the voice in the dark. Nashville lost its heartbeat tonight.” Vigils are sprouting spontaneously—candlelit circles outside Tootsie’s Orchid Lounge, where Struggle cut his teeth, fans scrawling lyrics on brick walls: “Burn the midnight oil, chase the devil’s tail.”

At 45, Struggle leaves behind his mother Jenni Eddy Jennings, his partner and three children (including Brianna), and a legacy etched in ink and asphalt. No autopsy details yet, but whispers from Music Row insiders point to a “sudden health event” during a low-key studio session—perhaps the toll of a life lived at full throttle. As Nashville’s skyline twinkles through the Cumberland fog, one thing’s clear: Struggle Jennings didn’t just rap about the struggle. He embodied it, wrestled it to the mat, and rose swinging. His final Instagram story, posted just hours before? A grainy clip of him strumming an acoustic “Waylon & Willie” riff at dawn: “One more outlaw tale before the sun catches up.”

The music world mourns, but in true Jennings fashion, it’s not with dirges—it’s with defiance. Crank the volume, pour one out, and let the outlaws ride eternal. Heaven’s got a new mixtape dropping soon.

Harlan Crowe is a senior writer at Rolling Stone, chasing the ghosts of Nashville’s renegades. In memory of Struggle: Stream Waylon & Willie tonight.