"Pony" is a song of desolation and exhaustion. It's about a man who has traveled the world and had all kinds of adventures, but now just wants to get back home. He's too wasted and worn out to remember the way, though, so he can only hope his pony knows.
While the song calls to mind someone travelling in the Old West or some other time in the past, some of the details are drawn directly from Waits' life. When he sings about being back in "Evelyn's kitchen," for instance, he's talking about his favorite aunt, Evelyn, who died during the making of Mule Variations.
According to Waits, Evelyn lived in Gridley, California, and had 10 children with her husband Chalmer. They had a dog named Gyp, also mentioned in the song ("with old Gyp curled around my feet").
In 1999, Waits told the Austin Chronicle, "I guess I've been far away from home, and have thought about her kitchen a lot and that a lot of people feel the same way when they've been far away from home. I dreamed about getting back home to her kitchen. That's why we put her in there - a tribute to Evelyn. The other people are just different people I've come across over the years - know, heard about, read about."
Waits told Bart Bull that the song is also about the Delta blues singer Skip James. He specifically mentioned James' songs "Hard Luck Child" and "Little Cow and Calf is Gonna Die Blues." Waits also mentioned Charlie Patton's "Pony Blues" as possibly mixed up in the tune.
Not since the earliest days of his career has Waits told linear stories in his songs. He's said himself that he likes to bury the autobiographical stuff. So, there's no conflict or contradiction in the two directions the song's coming from. What matters is where they intersect, and with this song that point of crossing is characterized by a sad, weary, desolately beautiful feeling of being too far gone from home.
A few places are mentioned in the song.
"I was full of wonder when I left Murfreesboro" is referring to the town of Murfreesboro, Tennessee. It's southeast of Nashville.
"Now I am full of hollow on Maxwell Street" refers to the Chicago Maxwell Street neighborhood, which is where the Chicago Blues originated.
"I walked from Natchez to Hushpuckena" is referring to two cities in Mississippi. Making this walk would take a person to Belzoni, Mississippi, a place where Skip James and Charlie Patton (the two musicians Waits cited as being part of the song) were said to play.
"Caught a blind out on the B and O" is referring to the Baltimore and Ohio Railroad. The term "a blind" used to mean a baggage car, which has no windows.
"A 44 will get you 99" sounds like a sinister reference to a gun, but a "44" was actually a common term used at lunch counters in the 1940s to mean a cup of coffee. A "99," meanwhile, was a lunch counter or soda-fountain manager.
Of course, it's also possible that the line really is referring to a gun, saying it will earn a 99-year prison sentence.
The lines, "I run my race with Burnt Face Jake, gave him a Manzanita cross" refers to the manzanita North American shrub. Waits told Barney Hoskyns in Mojo (1999): "Manzanita is a tree. Everything around the Sacramento Valley seems to be named after manzanita: Manzanita School, Manzanita Market, Manzanita Road. It's gnarled, twisted, blood-red wood."