Lyric discussion by Lazlo 

Just a few points about the placenames here....

This hobo's narrative begins in Murfreesboro, TN, which the narrator leaves to go see the world by bumming around and riding the rails (a recurring theme in Waits's work).

At the time when he tells this tale, he has ended up on Maxwell Street in Chicago, world-weary and without a penny to his name.

He describes his time bumming around Mississippi, when he once walked the 200 miles from Natchez to Hushpukina, and later ended up working in a sawmill in Belzoni -- where he reports he never received his wages.

Something happened in Belzoni (perhaps a confrontation with the mill owner who wouldn't pay him) and he had to "catch a blind out on the B&O", which means jumping a freight train owned by the Baltimore and Ohio line, standing on the linkage between the coal car and the adjoining freight car, a position which could not be seen by the engineer because the coal car blocks the view. It was a rough way to ride, but not as bad as "riding the rods" which was even more dangerous.

Presumably, the narrator shot someone and faced a charge of life in prison, thus "a .44 will get you 99". That's why he escapes to Talullah, a town in Louisiana, outside of the Mississippi state jurisdiction.

By the time he ends up in Chicago, telling his tale to the "boys" in the flop-house or out on the street, his days of slow-dancing with Ida Jane and sitting in Evelyn's warm kitchen with a hot cup of coffee and the dog lying on his feet are long gone dreams of his youth.

The lines of the chorus are ironic... he has no pony, he has no home, and the life he knew back in Tennessee is gone, never to be recaptured.

But the desire is still there. Now more than ever, in fact. Now he knows what he lost, what he threw away.

Maybe it was all worth it, but it sure is hard to think that when you're old and down on your luck in the market district of Chicago, spinning your tales of jumping trains with Blind Darby and Burned Face Jake.

You just hope that somehow, some way, you can make it back. That some force will sweep you up and carry you there, and you'll find yourself again in the arms of your childhood sweetheart, and someone will see you and know you and invite you in and the dog will be happy that you've returned and curl up next to you and fall asleep as you talk into the night, and there'll be a bed waiting for you, with clean sheets to sleep on, and clean water to wash in the next morning.

I hope my pony knows the way back home.

I like the song, but it's my understanding that the pony never left the gate. The rider became missing in action...action elsewhere:) The sequel to the song is the pony telling the rider to get the heck over here and stop waiting for something as unrealistic as a pony and a rider communicating via Internet;)

@jeffreystump, I think the song you're referring to there is "Get Behind the Mule" which is track 4 on the same record as "Pony".

wow, nice job, thanks

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