Crowell's first big break came while he was performing as a lounge singer, where one of his acoustic sets was heard by Jerry Reed. Crowell's own "You Can't Keep Me Here in Tennessee" caught the ear of Reed and his manager, and two days later, Reed recorded the song after signing Crowell to his publishing company. In 1975, Crowell moved to Los Angeles to join Emmylou Harris' Hot Band as a guitarist, and soon became one of her primary songwriters; among the Crowell compositions Harris first popularized were "Till I Gain Control Again," "Ain't Livin' Long Like This," "Leaving Louisiana in the Broad Daylight," and "Bluebird Wine." In 1977, Crowell exited the Hot Band to form his own group, the Cherry Bombs, and in 1978 released his first album, Ain't Living Long Like This; surprisingly, given that he had built his growing reputation as a songwriter, his first two minor hits -- "Elvira" and "(Now and Then, There's) A Fool Such as I" -- were both covers.

Also in 1978, Crowell began producing tracks for the album Right or Wrong, the American debut from singer/songwriter Rosanne Cash; around the time of the record's 1979 release, he and Cash married. In between recording his own 1980 sophomore record, But What Will the Neighbors Think, and producing Cash's commercial breakthrough Seven Year Ache, Crowell's songwriting career took full flight when "Leavin' Louisiana in the Broad Daylight" hit number one for the Oak Ridge Boys in 1980. Among his other significant compositions were "Till I Gain Control Again" (a number one for Crystal Gayle in 1983), "Shame on the Moon" (a Top Five pop hit for Bob Seger in 1982), "Long Hard Road (The Sharecropper's Dream)" (a 1984 number one for the Nitty Gritty Dirt Band), and "Somewhere Tonight" (a number one in 1987 for Highway 101).

In 1980, Crowell issued his own first hit, "Ashes by Now," which was a Top 40 pop crossover success; the follow-up, "Stars on the Water," was popular with both pop and country listeners. In 1981, he issued his third LP, a self-titled effort which was not commercially successful; when a fourth effort was rejected by his label, he turned his energies to writing and producing, most significantly helming Cash's 1987 masterpiece King's Record Shop. At Cash's urging, Crowell reignited his performing career in 1986 with the acclaimed Street Language, an eclectic effort co-produced by Memphis soul legend Booker T. Jones.

In 1988, Crowell finally broke through commercially with Diamonds & Dirt, a record which generated an unbroken string of five number one singles with "It's Such a Small World" (a duet with Cash), "I Couldn't Leave You If I Tried," "She's Crazy for Leavin'" (co-written by Guy Clark), "After All This Time," and "Above and Beyond." Keys to the Highway was also highly successful.

Crowell and Cash divorced in 1991, prompting both artists to document their marriage's dissolution with starkly confessional albums; Crowell's 1992 Life Is Messy featured guests Steve Winwood and Linda Ronstadt. Switching to MCA Records for Let the Picture Paint Itself in 1994, he followed with Jewel of the South the next year. In 1997, he formed the Cicadas with longtime backup musicians Steuart Smith, Michael Rhodes, and Vince Santoro. He married singer Claudia Church in 1998, and in 1999 wrote her country chart debut, "What's the Matter with You Baby." Crowell issued his first album since 1995, The Houston Kid, in 2001. Continuing in the autobiographical vein of that record, he released Fate's Right Hand in 2003, followed by The Outsider in 2005, and Sex and Gasoline in 2008. In 2012, Crowell released the album Kin in collaboration with best-selling memoirist and poet Mary Karr. Produced by Joe Henry, it included musical contributions from Lucinda Williams, Norah Jones, Kris Kristofferson, Vince Gill, Lee Ann Womack, Rosanne Cash, Chely Wright, and Emmylou Harris on songs Crowell and Karr co-wrote together.