His songs have been recorded by Johnny Cash, Waylon Jennings, Willie Nelson, Levon Helm, The Highwaymen, Travis Tritt, Vince Gill, Patty Loveless, Shawn Colvin, Bob Seger, Percy Sledge, Dailey & Vincent, and Emmylou Harris.

[5] Earle has appeared in film and television, most notably as recurring characters in HBO's critically acclaimed shows The Wire and Treme.

[13] In 1974, at the age of 19,[7] Earle moved to Nashville and began working blue-collar jobs during the day and playing music at night.

[11] Earle appeared in the 1976 film Heartworn Highways, a documentary on the Nashville music scene which included David Allan Coe, Guy Clark, Townes van Zandt, and Rodney Crowell.

Earle lived in Nashville for several years and assumed the position of staff songwriter at the publishing company Sunbury Dunbar.

[11] Connie Smith recorded Earle's composition "A Far Cry from You" in 1985 which reached a minor position on the country charts as well.

That same year he released a compilation of earlier recordings, entitled Early Tracks, and an album with the Dukes, called Exit 0, which "received critical acclaim" for its blend of country and rock.

[12] At that time a writer for the Chicago Sun-Times called Earle "a visionary symbol of the New Traditionalist movement in country music.

[16] According to Earle, he wrote the song "Over Yonder" about a death row inmate with whom he exchanged letters before attending his execution in 1998.

[8] His novel, I'll Never Get Out of This World Alive, was published in the spring of 2011 and a collection of short stories called Doghouse Roses followed that June.

[8][21] Earle responded by appearing on a variety of news and editorial programs and defended the song and his views on patriotism and terrorism.

[citation needed] In September 2007, Earle released his twelfth studio album, Washington Square Serenade,[27] on New West Records.

In the winter, he toured Europe and North America in support of Washington Square Serenade, performing both solo and with a disc jockey.

Guest artists appearing on the album included Tom Morello of Rage Against the Machine, Moorer, and his son Justin.

[32] Earle has recorded two other anti-death penalty songs: "Billy Austin", and "Ellis Unit One" for the 1995 film Dead Man Walking.

[citation needed] In 2010–2011, Earle appeared in seasons 1 and 2 of the HBO show Treme as Harley Wyatt, a talented street musician who mentors another character.

Earle released his first novel and fourteenth studio album, both titled I'll Never Get Out of This World Alive after a Hank Williams song, in the spring of 2011.

[20] The album was produced by T Bone Burnett and deals with questions of mortality with a "more country" sound than his earlier work.

[33] During the second half of his 2011 tour with The Dukes and Duchesses and Moorer, the drum kit was adorned with the slogan "we are the 99%" a reference to the Occupy movement of September 2011.

The song was released for sale the following day with all proceeds going towards the Southern Poverty Law Center, a civil rights organization.

[40] Earle was one of five artists who filed a class action lawsuit against Universal on June 21, in response to an earlier Times report on the fire.

[41] Earle was the musical director for the 2020 play Coal Country about the 2010 West Virginia mining disaster where 29 men died.

The play by Jessica Blank and Eric Jensen ran at the Public Theater in New York and was cut short by the start of the COVID-19 pandemic.

[42] Steve Earle features prominently in Love at the Five and Dime: The Songwriting Legacy of Nanci Griffith (Texas A&M University Press, 2024).

[44] Earle subsequently started DJing on a show on Sirius Satellite Radio called Hardcore Troubadour.

[59][60] During the 2016 election, he expressed support for Senator Bernie Sanders, whom he considered to have pushed Hillary Clinton to the left on important issues.

"[62] However, Earle has called for the American left to engage with the concerns of working class Trump voters, saying in 2017: "…maybe that's one of the things we need to examine from my side because we're responsible.

Earle criticized the conviction of six Satan's Choice bikers for a 1978 murder in Port Hope, arguing that the accused were innocent, framed by the ruthless Corporal Terry Hall of the Ontario Provincial Police's Special Squad.

And it comes down to the fact that people who can't afford decent legal representation—who are subject to something like this happening and turning out very badly—feed my kids.

His 2012 novel I'll Never Get Out of This World Alive describes the life of a morphine-addicted doctor in 1963 San Antonio before Roe v. Wade who treats gunshot wounds and provides illegal abortions to poor women.