A former staff writer for PolyGram Publishing in Nashville, Pettis' musical career was started in 1979 when Joan Baez covered one of his songs, "Song at the End of the Movie", on her album Honest Lullaby. Following that release, Pettis became heavily involved in the "Fast Folk movement" in New York in the 1980s alongside artists such as Shawn Colvin and Suzanne Vega. In 1984, Pettis released his first independent solo album, Moments, followed by a string of releases for High Street Records; While the Serpent Lies Sleeping, Tinseltown and Chase the Buffalo.

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