50. "Not Dark Yet" (1997)
A few months before Dylan released 1997's Time Out of Mind, he was hospitalized with a severe heart infection that made him believe that he'd "be seeing Elvis soon." "Not Dark Yet" was finished long before this illness had set in, but the hauntingly beautiful song seemed to almost foretell it. Against Daniel Lanois' trademark swampy production, Dylan sings in the weary and weathered voice of a man facing the twilight of his life. "I was born here and I'll die here against my will," he sings. "I know it looks like I'm moving, but I'm standing still." Dylan had been recording death-obsessed songs since his very first album in 1962. Here, he was a road-weary 55, in the middle of his Never Ending Tour, and you can hear every one of those years in that voice.