Williams was in a tight spot. While his name, face, and uncanny vocal resemblance to his grandfather almost guaranteed him a thriving country audience, he had no patience for Nashville's squareness and rigid control. He and his Damn Band could wow a crowd with a spot-on set of gorgeous country balladry and spirited honky tonk. But III could just as easily shift gears into screeching, Black Flag-style punk rock with his hard-rocking combo Assjack. He was the kind of anomaly enormous record companies couldn't stand -- eminently marketable, yet defiantly unpredictable.

Curb issued Hank III's proper debut in September 1999. Entitled Risin' Outlaw, it presented 13 rough-hewn country numbers colored by III's honky tonking vocals. And while he played his share of "country" gigs to support it, Williams also appeared at the 2001 Vans Warped Tour alongside punks like Rancid. The irascible III also dismissed Outlaw as a label-controlled fiasco almost immediately after its release. After a few years of touring and trying like mad to be released from his Curb contract, III returned to wax in early 2002 with Lovesick, Broke & Driftin'. While Outlaw had featured material from outside writers, the new LP was all Hank III but for a previously released cover of Bruce Springsteen's "Atlantic City." He also produced, recorded, and mixed it by his lonesome in just two weeks.

At this point, Hank III's relationship with Curb became even more strained. The label refused to release his appropriately named This Ain't Country LP, which featured songs like "Life of Sin" and "Hellbilly." At the same time, it refused to grant Hank III the rights to issue it on his own. He and the record company reached an impasse, which III only exacerbated with the "F*** Curb" T-shirts he sold through his thriving website. Thrown Out of the Bar, his third honky tonk album, was scheduled for release in 2003, as was the long-awaited This Ain't Country. Additionally, Hank III issued extremely limited-edition releases through his website (often in quantities of 100 or less) and continued to play bass in Superjoint Ritual, the brutal side project of Pantera frontman Phil Anselmo.

The double-disc Straight to Hell was released March 2006 on Bruc Records (the fledgling rock division of Curb). The first CD contained songs with elements of traditional country warped to fit Hank III's rebel attitude, while the second disc boasted only one song that featured just III, his guitar, ambient noises, and a slight story that those coming down from drugs might enjoy. Ever in the outlaw mode, Hank III released Damn Right, Rebel Proud in 2008. His fourth and supposedly final album for Curb, The Rebel Within, followed in the spring of 2010. And in a move that hardly pleased Hank III, Curb next repackaged This Ain't Country, the oft-bootlegged project that started the acrimony between III and the label in the first place, with additional unreleased material thrown in, as Hillbilly Joker in 2011. Curb managed to get an 8th album out of a lapsed six-album contract by releasing another set of previously unreleased material, Long Gone Daddy (mostly outtakes from 1999's Risin' Outlaw and 2002's Lovesick, Broke & Driftin') in 2012.