Kelly Willis

Liberated from the Nashville playbook and emboldened by a jolting shot of nothing-left-to-lose, she set about making her next record in Austin her way. The end result, 1999’s aptly-titled What I Deserve, changed everything. “A big part of making that record was me thinking, ‘I’ll probably never get to make another one after this, so if this has to be my swan song, I’m not going to compromise,’” she says today. “That was a really big sea change for me to take the reins like that, and it was incredibly satisfying and gratifying that it then found a home with [independent label] Ryko and did so well. It was a pivotal moment that fueled the rest of my career.”

A bracingly assertive showcase not just for Willis’ masterful control of her “enormous voice” (per noted “Consumer’s Guide” critic Robert Christgau) but also for her burgeoning songwriting chops (be it solo or collaborating with the likes of John Leventhal and the Jayhawks’ Gary Louris), What I Deserve may not have made Kelly a household name on the order of Shania, Faith, or Reba, but it clinched her standing as a bona fide darling of the national (and international) alt-country scene. Writers from No Depression to Rolling Stone cheered her “comeback,” and fans in her adopted hometown voted it “Album of the Year” in the Austin Music Awards. A decade later would find her inducted into the Austin Music Hall of Fame.