Crowell started early in music as the eleven-year-old drummer in his father's band, the Rhythmaires, which delivered a hard-core brand of honky-tonk, Texas swing, and Appalachian folk music to the good people of Houston's east side in the late 1950s. He arrived in Nashville in the early 1970s, determined to make it as a songwriter. He was the right man in the right place at the right time, and fell in with a group of songwriters at Bishop's Pub a combination soup kitchen and open-mike stage where he passed the hat alongside Guy Clark, Townes Van Zandt, Robin and Linda Williams, Steve Earle, John Hiatt, Lucinda Williams, and others.
Crowell could have wound up as just another talented but unheralded Nashville songwriter (and there are hundreds, possibly thousands), but fate's right hand picked him up and spun him round. Two of his songs came to the attention of Emmylou Harris. She recorded "Bluebird Wine" on her first album and "Till I Can Gain Control Again" on her second, and soon afterward Crowell was living in L.A. as rhythm guitarist, harmony singer, and songwriter for Harris's renowned Hot Band. When he left the band two years later, a contract with Warner Brothers was waiting. A wide-ranging career in recording (ten solo albums to date), producing (Rosanne Cash, Guy Clark, and others), and songwriting (hundreds of versions of his songs covered by just about everybody) followed.