5. 'Not Dark Yet'
Dylan was just 56 when he recorded Time Out of Mind, but he crammed a lot of living into those years and already felt like an old man facing the inevitably of death. Regret, loss and mortality come up again and again. The starkest song is "Not Dark Yet," a six-and-a-half-minute track that is surely one of the most depressing and moving songs in Dylan's catalog. "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/Every nerve in my body is so vacant and numb/I can't even remember what it was I came here to get away from."