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I think "Shut and Die Like An Aviator" was Earle's attempt at black humor-at that time in his life he was hopelessly addicted to heroin (which he had been for around 20 years or so) was teetering on the edge of diaster and was shortly arrested thereafter for disturbing the peace, I think, and he wound up kicking out the window of a police car.
He did time in prison which allowed him to sober up, like David Crosby. It probably saved his life-I saw a photo of him from around this time and he looked like a walking corpse-literally like he was laughing in the face of death. He was losing his teeth because of his bad habits and wound up having to have implants in his jaws.
He truly has risen like a Phoenix-he is as good as he has ever been and presumably is clean. One of the most moving shows I've ever seen was the concert he did in his old cell block which was broadcast on MTV not long after he got out. Kinda like an updated version of Johnny Cash at Folsom Prison, except Earle DID time behind those same bars.
If you want to hear a true prison song, listen to Ellis Unit Number Nine (the Death Row Cell) on the soundtrack for Dead Man Walking. You can hear the doors slamming on the singer's life.
He's not for everybody, which is why Steve Earle is so great. He made it very clear early in his career he wasn't going to kiss ass to make it in Nashville, and they made it clear that they didn't want his kind (talented, opinionated songwriter) in Music City. So far he hasn't needed 'em.
Great live perforrmer and one of the best songwriters alive, one of the few equal to Bruce Springsteen, INMHO.