I think this song can be compared with Sad-Eyed Lady of the Lowlands, another epic-length Dylan tune, this one from Blonde on Blonde. Beside the Lowlands/Highlands contrast, see the lyric: “Wouldn’t know the difference between a real blonde and a fake”. Perhaps the waitress is Sara Lowndes, his former wife?
I think this song can be compared with Sad-Eyed Lady of the Lowlands, another epic-length Dylan tune, this one from Blonde on Blonde. Beside the Lowlands/Highlands contrast, see the lyric: “Wouldn’t know the difference between a real blonde and a fake”. Perhaps the waitress is Sara Lowndes, his former wife?