I have always found this song to be quite powerful and to have a hidden meaning, though I didn’t realize it as such until the last decade or so of my life. It was a big deal when the song and album were released in 1985, as this was the very first country video MTV had ever aired.
You know, back when they actually played music?
You have Willie Nelson lending his voice in the first part of the song, saying he was a roving outlaw who pillaged in the early 20th century western United States as he pleased. He was hung by “bastards” in the spring of 1925.
Kris Kristofferson is the voice of a sailor who has a fatal accident in the Gulf of Mexico during a storm of some kind.
Waylon Jennings voices a builder on what’s now referred to as the Hoover Dam south of Las Vegas (a place called Boulder on the wild Colorado River, buried in a great tomb that knows no sound), again the victim of an apparent accident.
The song’s most powerful verse goes to Johnny Cash, talking about how he flies a starship some point in the future, saying that yes, he was once a highwayman, and the sailor, and a worker on the Boulder/Hoover Dam. What I get out of it is that a life can take on many possible roles, and can end many ways by choices or by fate. However, your spirit lives on forever, and isn’t taken from you once your respective life ends. There is a bigger picture that you play a part of than even the one present life you currently have has in store for you.
That’s what I get out of that song anyway, and it’s a beautiful sentiment.