Guitarist David Grubbs and drummer John McEntire had played together in the post-hardcore band Bastro with bassist Clark Johnson. When Johnson left Bastro in 1991 to attend law school, Bundy K. Brown joined and the group began writing new material, later documented as the instrumental live album Antlers: Live 1991. These songs were then reworked as quieter, acoustic versions for The Serpentine Similar as Bastro became Gastr del Sol.