Lyle Lovett was one of the most distinctive and original singer/songwriters to emerge during the '80s. Though he was initially labeled as a country singer, the tag never quite fit him. Lovett had more in common with '70s singer/songwriters like Guy Clark, Jesse Winchester, Randy Newman, and Townes Van Zandt, combining a talent for incisive, witty lyrical detail with an eclectic array of music, ranging from country and folk to big-band swing and traditional pop.
Lovett's literate, multi-layered songs stood out among the formulaic Nashville hit singles of the late '80s as well as the new traditionalists who were beginning to take over country music. Drawing from alternative country and rock fans, Lovett quickly built up a cult following which began to spill over into the mainstream with his second album, 1988's Pontiac. Following Pontiac, his country audience declined, but his reputation as a songwriter and musician continued to grow, and he sustained a dedicated cult following throughout the '90s.