Grubbs had moved to Washington, D.C. to attend Georgetown University where he started an early version of Bastro with bassist Dan Treado, who soon left.

After their first release, Bastro toured with the band My Dad Is Dead, whose drummer at the time was Oberlin College percussion major John McEntire.

McEntire soon joined Bastro, replacing the drum machine, and the trio recorded a full-length album with former Squirrel Bait engineer Howie Gano.

Returning to the studio with engineer Brian Paulson, they recorded faster versions of their songs and these—along with "Shoot Me a Deer" and "Wurlitzer" from the first session—comprised the band's first LP Diablo Guapo (Spanish for "Handsome Devil").

During this period Johnson was enrolled at Northwestern University in the Chicago suburb of Evanston, Illinois, and Grubbs also played in the band Bitch Magnet, resulting in a two year break before Bastro's second album, Sing the Troubled Beast.