After spending over a decade playing drums in various rock bands, singer/songwriter John Howie eventually exchanged his kit for a six-string acoustic guitar and a handful of broken-hearted, whisky-drinking country ballads to form Two Dollar Pistols. Taking a cue from old-time country-folk from the Sun Records era of the 1950s, Merle Haggard, and George Jones, Howie remained in his home state of North Carolina rather than jumping ship to the carbon-copy, commercialized country of Nashville. With the accompaniment of guitarists Greg Hawks and John Prince, drummer Chris Phillips (who can also be found behind the set in the Squirrel Nut Zippers), bassist Jack Campbell, fiddler Jon Kemppainen, and steel guitarist Steve Watson, Two Dollar Pistols' constant gigging was eventually rewarded with a deal on Hep-Cat Records, who put out their debut, On Down the Track, in 1997. Their follow-up, Step Right Up, was released the next year on Yep Roc. An EP of duets with Tift Merritt became a fan favorite, prompting Howie to make lineup changes. Guitarist Scott McCall, bassist Neal Spaulding, and drummer Mark Weaver joined the band and hit the road to promote the album. This lineup lasted into 2002, when the group recorded and released You Ruined Everything. Hands Up! followed two years later.