In 1980, Keen graduated from Texas A&M and moved to Austin, Texas, where he began writing for a newspaper. Soon he was performing in Austin's nightclubs and live music venues, building a solid following. In 1984 he financed the recording of his own EP and distributed it regionally. In 1986, He moved to Nashville, Tennessee. Discouraged by the polish of the new country sound and unable to land a recording contract, Keen moved back to Austin. In 1989 he released his national debut album, West Textures. His 1993 release, A Bigger Piece Of Sky, gained wider acclaim, both amongst fans and critics. Over the next ten years, Keen would continue to write, record, perform and tour. In 1994 he performed in the musical Chippy. Keen's 1997 album Picnic features a picture of Keen's own car in flames at Willie Nelson's 1974 Fourth of July picnic/concert. He tells the story on the No. 2 Live Dinner album in the introduction to the song "The Road Goes on Forever."