Bill Callahan

Bill Callahan first appeared in the tape-trading underground in the late '80s with a series of self-released cassettes under the deliberately meaningless name Smog. 1990's Sewn To The Sky, a willfully rough-edged LP strongly reminiscent of both outsider hero Jandek and the more experimental side of DIY godfather R. Stevie Moore, gained enough attention for the peripatetic Maryland native to sign with Chicago's emergent Drag City label (where, admirably, he has stayed ever since). The homemade nature of Smog's earliest Drag City releases caused them to be lumped in with the nascent lo-fi scene, but Callahan quickly proved himself to be an old-fashioned singer-songwriter in the lyrics-forward mold of Leonard Cohen or Joni Mitchell, abandoning his early solo approach in favor of folk and country-tinged full-band arrangements closer in spirit to his labelmate Will Oldham than Pavement. Because Callahan habitually sings in a conversational, deadpan baritone--the rough midpoint between Stephin Merritt and Johnny Cash--he has throughout his career been pigeonholed as a gloomy miserablist. But although Callahan's lyrics are certainly familiar with the dark side, a quirky sense of humor runs through his oeuvre as well: note the dorkily smutty spoonerism of the album title Dongs of Sevotion, or "Eid Ma Clack Shaw," which features a verse performed in a self-invented language. Callahan retired the Smog identity after 2005's A River Ain't Too Much To Love, continuing his musical career under his own name with 2007's Woke On A Whaleheart.