The debate has forever raged about what this song means. The most popular opinions are drugs or suicide. I’ve always believed the latter, but it doesn’t really matter.
It took me several listens before I realized it was about anything so dark. Not listening closely to the lyrics will do that to you. It’s a beautiful melody that can deceive you into thinking it might just be about a woman named Kathleen. In part, I believe it is. Kathleen could be a lost love the narrator longs to see once again. How he’ll achieve that goal is wherein the darkness lies.
Townes Van Zandt was one of our greatest singer-songwriters. He said himself that he didn’t expect to live long, and many consider that a bit of a premonition of his death at the age of 52. Truthfully, it’s a bit of a miracle he lasted that long considering his long history of alcohol and drug abuse. Though born in an affluent family, he was not immune to mental illness, something that probably drove his incredible talent but also shortened his life.
I won’t try to tell his life story. You can go research that on your own. More importantly, you should probably research some of the music of Townes Van Zandt.