Among the large contingent of talented songwriters who emerged in Texas in the 1980s and 1990s, Robert Earl Keen struck an unusual balance between sensitive story-portraits ("Corpus Christi Bay") and raucous barroom fun (&"That Buckin' Song"). These two song types in Keen's output were unified by a mordant sense of humor that strongly influenced the early practitioners of what would become known as alternative country music. Keen, the son of an oil executive father and an attorney mother, was a native of Houston. His parents enjoyed both folk and country music, and his own style would land, like that of his close contemporary Nanci Griffith, between those genres. Keen wrote poetry while he was in high school, but it wasn't until he went to journalism school at musically fertile Texas A&M that he learned to play the guitar. He and Lyle Lovett became friends and co-wrote a song, "This Old Porch," which both later recorded.

Keen made a splash in Austin with his debut album, No Kinda Dancer, self-financed in 1984 to the tune of 4,500 dollars. He moved to Nashville during the heady experimentalism of the 1980s that saw Lovett and k.d. lang hit the country Top Ten, but he soon returned to Austin. Texas landscapes and residents provided Keen with creative inspiration, as his second album, West Textures, made clear; that album yielded one of Keen's signature numbers, an ambitious crime-spree song called "The Road Goes on Forever." Now recording for Sugar Hill, Keen recorded a live album shortly after West Textures but waited several years to release a studio follow-up, 1993's A Bigger Piece of Sky. After that album (which contained "Corpus Christi Bay") came Gringo Honeymoon (1994), which merged Keen's story songs with the emerging sounds of alt-country: guitars were laid down by the influential Austin musician Gurf Morlix, who later produced albums for both Keen and Lucinda Williams, and a young Gillian Welch provided harmony vocals.