While he was in Nashville, Earle worked blue-collar jobs during the day; during the night, he wrote songs and played bass in Guy Clark's backing band, appearing on a cut on Clark's 1975 album Old No. 1. Steve stayed in Nashville for several years, making connections within the industry and eventually landing a job as a staff writer for the publisher Sunbury Dunbar. After staying in Nashville for a few years, he grew tired of the city and returned back to Texas. There he assembled a backing band called the Dukes and began playing local clubs. A year later, he returned to Nashville, where he married his second wife, Cynthia. The marriage was short-lived and he quickly married Carol, who gave birth to Earle's first child, a son named Justin Townes Earle. Carol helped straighten Earle out, at least temporarily; for a while, he cut back on substances and concentrated on music.

Publishers Roy Dea and Pat Clark signed Earle as a songwriter in the early '80s. Dea and Clark brought "When You Fall in Love" to Johnny Lee, who took the song to number 14 on the country charts in 1982; shortly before the success of "When You Fall in Love," Carl Perkins cut Steve's "Mustang Wine," and Zella Lehr recorded two of his songs. With his reputation as a songwriter growing, Earle wanted to become a recording artist in his own right. Dea and Clark had recently formed an independent record label called LSI and the pair signed Earle.

Earle's first release was an EP called Pink & Black in 1982. The record featured a formative version of the Dukes and earned good reviews. One writer, John Lomax, sent the EP to Epic Records, which was impressed enough by the record to sign Earle in 1983. Shortly, before the signing of the contract, Lomax became Earle's manager. Although the prospect of being signed to a major label seemed promising, relationships between Epic and Earle quickly soured. After releasing the Pink & Black track &"Nothin' But You" as a single, Epic sat on the song, refusing to promote the record; instead, they concentrated on their new signing. Earle entered the studio and cut an album of neo- ockabilly songs that the label was reluctant to send to radio and, therefore, they refused to release the record. Epic suggested Earle re-enter the studio with a new, more commercially oriented producer, Emory Gordy, Jr. The pair cut four more songs which were released as two singles, but the records failed.

With his recording career going nowhere, Earle lost his publishing contract with Dea and Carter. He moved over to Silverline Goldline, where he met Tony Brown, a producer at MCA Records. At the end of 1984, Epic dropped Earle from their roster. In early 1985, Brown persuaded MCA to sign Earle, and Lomax was fired as his manager. In 1986, Earle's debut album, Guitar Town, was released. Upon its appearance, Earle was grouped into the ew traditionalist movement begun by Dwight Yoakam and Randy Travis, but he also gained the attention of ock critics and fans who saw similarities between Earle's populist sentiments and the heartland rock of Bruce Springsteen and John Mellencamp. Guitar Town became a hit, with its title track becoming a Top Ten single in the summer of 1986 and "Goodbye's All We've Got Left" reaching the Top Ten in early 1987. Following the album's success, Epic quickly assembled a compilation of previously unreleased Earle tracks, entitling it Early Tracks and releasing it in early 1987. Later that year, he released his second album, Exit 0, which bore a shared credit for his backing band the Dukes, which signalled the more ock-oriented direction on the album. Like the debut, Exit 0 was critically acclaimed and sold well, even if it didn't match the levels of the debut.

Though his career was taking off, Earle's personal life was becoming a wreck. He had divorced his third wife, married a fourth named Lou, whom he quickly divorced, and then he married a sixth wife named Teresa Ensenat, who worked for MCA. He was also delving deeper and deeper into drug and alcohol abuse. With his third album, 1988's Copperhead Road, Earle's ock & roll flirtations came to the forefront and country radio responded in kind; none of the songs from the album charted or received much airplay. However, album rock radio embraced him, sending the album's title track into the album rock Top Ten, which helped make the album his highest charting effort, peaking at number 56. Not only had Copperhead Road been accepted by AOR, but it established him as a star in Europe; the duet with the Irish punk-folk group the Pogues on Copperhead Road signalled he had an affection for the area. In the late '80s, Earle frequently toured England and Europe and even produced the alternative rock band the Bible.

Earle's acceptance by the ock community didn't please the country establishment in Nashville. Although it seemed for a time that Earle wouldn't need Nashville anymore, his newfound success quickly began to collapse. Uni, a division of MCA Records, had released Copperhead Road instead of MCA proper, and just before the album went gold, Uni went bankrupt, taking Copperhead Road along with it. Meanwhile, Earle's addictions and fondness for breaking rules began spinning out of control. On New Years' Eve, he was arrested in Dallas for assaulting a security guard at his own concert; he was charged with aggravated assault, fined 500 dollars, and given a year's unsupervised probation. Sandie, his first wife, sued for more alimony and he was served with a paternity suit by a woman in Tennessee. The title of his 1990 album, The Hard Way, reflected his problems, as did the record's tough, dark sound. Though the record was critically acclaimed and spawned a minor AOR hit with "The Other Kind," it received no support from the country market and quickly fell off the charts.

The commercial failure of The Hard Way was just the beginning of a round of serious setbacks for Earle. Later in 1990, he recorded an album of material that MCA refused to release. Instead, the label decided to release the live album Shut Up and Die Like an Aviator in 1991. At the end of the year, MCA decided not to renew Earle's record contract. For the next several years, Earle was severely addicted to cocaine and heroin and had several run-ins with the law. In 1994, he was arrested in Nashville for possession of heroin and was sentenced to a year in jail. He served in a rehab center instead of jail. This time, the treatment worked.

Late in 1994, he was released from the rehab center and he began working again. In 1995, he signed to Winter Harvest and released the acoustic Train a Comin', his first studio album in five years. Train a Comin' received terrific reviews and strong sales, despite Earle's claim that the label botched the album's song sequence. The attention led to a new record contract with Warner Bros., who released I Feel Alright in early 1996, again to strong reviews and respectable sales. Earle had returned from the brink and re-established himself as a vital artist. In the process, he won back the country audience he had abandoned in the late '80s. The Mountain, a luegrass record cut with the Del McCoury Band, followed in 1999, and a year later Earle returned with Transcendental Blues.

While Earle had long displayed a strong political streak (particularly in his opposition to the death penalty), his leftist views took center stage on his 2002 album Jerusalem. Written and recorded in the wake of the terrorist attacks of September 11, 2001, Jerusalem dealt openly with Earle's divided feelings about America's "war on terror" and the West's ignorance of the Islamic faith, and included a song about John Walker Lindh, a young American who was discovered to be fighting with Taliban forces, called "John Walker's Blues." Earle's refusal to condemn Lindh in his lyrics quickly made the song (and the album) a political hot potato, but Earle embraced the controversy and became a frequent guest on news and editorial broadcasts, defending his work and clarifying his views on terrorism, patriotism, and the role of popular artists in a time of crisis. Earle's tour in support of Jerusalem was documented in the 2003 concert film and live album Just an American Boy, and in the summer of 2004, as the American occupation of Iraq dragged on and an upcoming presidential election loomed in the minds of many, Earle released The Revolution Starts...Now, an album of songs informed by the war in Iraq and the abuses of the George W. Bush administration. Live at Montreux, recorded at a 2005 show, was released in 2006, followed by Washington Square Serenade in 2007. ~ Stephen Thomas Erlewine, All Music Guide