The Relisten: Hank III — Risin’ Outlaw

In 1999, country music didn’t quite know what to do with Hank Williams III.

Risin’ Outlaw sounds like that confusion.

Too traditional for where Nashville was headed. Too polished for the artist Hank III would become. Too tied to the family name for a guy who would spend years trying to outrun it.

He would later distance himself from the record. You can understand why.

But that doesn’t make it any less important.

Released September 7, 1999, Risin’ Outlaw arrived in the middle of the sexy tractor boom that directly predated bro country. The late ’90s/early 00's had great country records, but country radio as an industry had largely settled on the Toby Keith/Kenny Chesney lane.

Into that came this skinny, tattooed third generation legacy act sounding like he’d wandered in from another decade. Or planet.

There are moments on Risin’ Outlaw when Hank III’s voice feels almost unsettlingly connected to his grandfather’s. Not in a way that sounds like impersonation...it's just in the genes and nasaly twang. It also became part of the problem.

Hank III was carrying around one of the heaviest last names in American music before he had really figured out what kind of artist he wanted to be. He had already participated in the Three Hanks project that electronically paired three generations of Williams voices. Then his first proper album arrived with a title like Risin’ Outlaw and a marketing story almost impossible to separate from the bloodline. It made him hate the machine he was already weary of before he'd even started.

He has never been subtle about his feelings toward this album. Even when it was new, Hank III complained that the production was too slick and too Nashville. In one interview, he dismissed the record and said he was already looking toward the next one. Years later he was still talking about the frustration of working with a producer and not having complete control over his sound.

By Lovesick, Broke & Driftin’ in 2002, and especially Straight to Hell four years after that, Hank III had ripped away almost every guardrail. The music got nastier, louder, stranger and more completely his. Punk and metal weren’t just side interests anymore. They were fully part of his music. The clean division between the country singer and the guy who loved the Melvins essentially disappeared.

27 years later, the supposed problem with the record is also part of what makes it so good.

There is absolutely some Music Row gloss on Risin’ Outlaw. The players are immaculate. The production is controlled. Nothing here has the dangerous, almost car crash quality Hank III would eventually chase. But calling this thing slick in 2026 almost feels funny.

Put it next to the country radio records surrounding it in 1999 and it sounds practically prehistoric.

Fiddle. Steel guitar. Upright bass. Train rhythms. Songs about drinking, leaving, loneliness and people with no apparent interest in improving themselves.

The record opens with “I Don’t Know,” and immediately there is that voice. From there, the album moves through “You’re the Reason,” “If the Shoe Fits,” Wayne Hancock’s “87 Southbound,” Buddy Miller’s “Lonesome for You,” “Devil’s Daughter” and Johnny Cash’s “Cocaine Blues.” It closes with a particularly strong three-song stretch: “Thunderstorms and Neon Signs,” “Why Don’t You Leave Me Alone” and “Blue Devil.”

Wayne Hancock wrote it, but Hank III sounds completely at home inside it. The song carries exactly the kind of romanticized roadside loneliness that would become such an important piece of the alt-country and Texas/Red Dirt world...highways, bars, weather, neon and the pull of somewhere else.

Hank III wanted distance from the Williams museum legacy piece people were trying to make him into. At the same time, he possessed one of the most naturally cool country voices of his generation.

Nashville wanted a marketable outlaw. He wanted something considerably messier. And real.

Sitting between those two ideas is Risin’ Outlaw.

That is why calling the album merely a false start misses what happened here. The record appeared during the same general period when another country music ecosystem was beginning to grow louder outside mainstream radio. Americana was becoming more defined. Texas and Red Dirt artists were building audiences without waiting for Nashville’s permission. Jack Ingram, Charlie Robison, Pat Green, Robert Earl Keen, Cross Canadian Ragweed and others were either already moving or about to move through that opening.

In the Americana world, Risin’ Outlaw was noticed immediately. Hank III never neatly belonged to any of those scenes. That was sort of the point. He was and is singular.

But he became an important piece of the same larger rebellion against the machine.

There is a straight line between this era and much of the independent country music explosion that followed. The Sturgills and Childers came in the wake.

Artists deciding country music could be older and younger at the same time.

That honky-tonk could live next to punk rock. That Waylon and Black Flag didn’t necessarily have to occupy different record collections. That Nashville did not get the final vote on what counted as country music.

This record is a snapshot of an artist caught at the exact moment before he figured out how to blow the whole thing up. Sometimes a record becomes bigger than the intentions of the person who made it.

And 27 years later, Risin’ Outlaw still sounds like a landmark.

Not because Hank III had arrived. Because you can hear him trying to get out. And in doing so, he drew a map that others could follow and have for 27 years going.