A group whose chaotic trajectory seemed destined to end in collapse, Whiskeytown nonetheless built one of alt-country’s most devoted underground audiences before its demise. Nearly every narrative pinned the relentless internal friction on frontman Ryan Adams, a precocious songwriter whose moments of inspiration were inseparable from a combustible disposition and heavy drinking. His reputation for onstage eruptions and wildly inconsistent shows fueled repeated clashes with fellow members, some of them erupting in public, which in turn produced a revolving cast of players. Across the band’s half-decade run, however, Whiskeytown still generated a body of gripping recordings that only deepened the aura surrounding its volatile leader.
The outfit took shape in Raleigh, North Carolina, in 1994 when twenty-year-old Adams—fresh from punk circles and newly enamored of Gram Parsons—teamed with fiddler and occasional vocalist Caitlin Cary, guitarist Phil Wandscher, bassist Steve Grothmann, and drummer Eric “Skillet” Gilmore. A seven-track EP titled Angels appeared on the local Mood Food imprint in 1995, followed in early 1996 by the full-length Faithless Street. Saturated with the influences of Parsons, Uncle Tupelo, and the Replacements, the album drew enthusiastic notices from the alt-country community, particularly No Depression, and a South by Southwest showcase secured a contract with Geffen’s Outpost subsidiary. A collection of early material, Rural Free Delivery, surfaced shortly afterward. In 1997 the band delivered its major-label bow, Stranger’s Almanac; by then bassist Jeff Rice and drummer Steven Terry had already replaced the original rhythm section, and Wandscher departed in the wake of the summer release.
The subsequent tour proved contentious, cementing Adams’s bad-boy image, and when the dust cleared only Adams and Cary remained. Multi-instrumentalist Mike Daly joined, contributing keyboards, guitar, pedal and lap steel, mandolin, mandocello, and dulcimer while co-authoring much of the next batch of songs. Additional players, among them ex-fIREHOSE guitarist Ed Crawford and returning original drummer Gilmore, cycled through rapidly. A workable studio configuration nonetheless held together long enough to finish the third album, Pneumonia, in 1999. Corporate reshuffling at the label kept the record on ice, allowing it to circulate widely on bootlegs and build a fervent cult reputation. With its future uncertain, Whiskeytown disbanded. Adams issued his solo debut Heartbreaker in 2000, the same year Cary released her own EP, Waltzie. Pneumonia finally emerged in 2001 on Universal’s Lost Highway imprint, earning some of the group’s highest critical marks for its wide-ranging sound. Adams’s profile as an indie figure continued to rise, while Cary remained active with frequent recordings throughout the 2000s.
