94. "Highlands" (1997)
Many of Dylan's greatest albums end with an epic that takes up the entire side of a record, and "Highlands" is the most epic of them all. Over the course of 16 minutes, Dylan talks to a waitress, orders softboiled eggs, name-checks Erica Jong and Neil Young and laments that life is passing him by. "All the young men with their young women looking so good," he sings. "Well, I'd trade places with any of them in a minute, if I could." He was only 56 when Time Out of Mind came out, but the fear of death is all over the album. Dylan has claimed that "Highlands" is built around a Charlie Patton riff, but nobody has found any riff that sounds remotely like it.