In this song, Dylan mixes lyrics of his own with lyrics from old Blues songs by the likes of Charlie Patton, Brownie McGhee and Leroy Carr. At face value, it seems to be expressing a sense of world-weariness, but some fans argue that, if you look hard enough, you will discover that it is actually about sexual frustration and is full of innuendo!
The title is suggesting life is fundamentally sad. While it takes a lot to make us laugh, it takes something as simple and as mundane as a train (and its consequent associations, such as lovers leaving town) to make us cry.
There is an alternative version of this song called "Phantom Engineer." It is faster, and has slightly different lyrics. It can be found on The Bootleg Series Volumes 1–3.
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