The all-star roots-pop outfit the Continental Drifters was formed in Los Angeles in late 1991 by ex-Dream Syndicate bassist Mark Walton and expatriate New Orleans musicians Carlo Nuccio (drums) and Ray Ganucheau (guitar); after enlisting guitarist Gary Eaton and keyboardist Danny McGough, the group played each Tuesday night at the Hollywood club Raji's and attracted a fervent local following. Over time, the Continental Drifters' roster swelled to include a number of auxiliary players including ex-dB Peter Holsapple, his wife Susan Cowsill and former Bangle Vicki Peterson; after McCough left the group, Holsapple assumed keyboard duties full-time. Their debut single, "The Mississippi," followed on Bob Mould's S.O.L. label in 1992; Cowsill and Peterson soon joined on a permanent basis as well.

When Nuccio and Ganucheau decided to move back to New Orleans, it was decided that the Continental Drifters would continue on, with various members flying cross-country to attend gigs; when that idea proved too costly, Jacobs, Holsapple and Cowsill all relocated to the Big Easy as well, and although Eaton eventually quit the group, Peterson ultimately followed to Louisiana too. Ganucheau soon exited, and guitarist Robert Maché was recruited as his replacement; this lineup recorded the Drifters' self-titled 1994 debut LP, which earned significant critical acclaim. After's Nuccio departure, new drummer Russ Broussard signed on; by 1997 the Drifters had yet to land a major label contract, so they recorded the single "Christopher Columbus Transcontinental Highway" for the tiny Black Dog label; the full-length Vermilion followed in mid-1998. Holsapple and Cowsill ended their romantic partnership in 2000 when they divorced, however they continued to work together in the band.