Songfacts®:

• "If you wanna be an outlaw you can never go home," Steve Earle sings on this track, warning those striving to join the outlaw ranks that there is a price to pay.
  
  Earle has long been associated with the "Outlaw Country" movement, and earned all the badges to show for it: drinking problem, divorces, instability. In a Songfacts interview with Earle, he talked about what the term really means. "What some people refer to as Outlaw Country, it was about artistic freedom," he said. "They were called outlaws because they wanted to make records the way they wanted. They discovered that rock had that artistic freedom that they didn't have. Or at least perceived that they did, and that's what that was all about."
• This is the title track to Earle's 17th studio album, which took on a country feel after he started it with two songs he wrote for the TV series Nashville: "If Momma Coulda Seen Me" and "Lookin' For A Woman." He was listening to a lot of Waylon Jennings at the time (specifically his 1978 album Honky Tonk Heroes), which set the tone - Jennings was a pioneer in the Outlaw Country movement.
• Willie Nelson sings the second verse on this track, which Earle wrote specifically for him. It gave Earle an excuse to visit Maui, where Nelson stayed for the winter.