I absolutely love the absurdist wit on Po’ Boy. Its whimsical nature, the humour and cheeseball lines get me every time. And the music is so playful, yet somehow also poised and nuanced. I’m starting to sound like a broken record, but this is another much-underrated song from Dylan, and it certainly came out of left field, especially in his later career catalogue.

To me, Po’ Boy sends me back to the farce and folly of his 1964 song I Shall Be Free No. 10. I was so entertained by the funny lyricism and wordplay in that song that I led my division team to sing it for a Music Night in the mid-1990s. Po’ Boy doesn’t get as silly as that one, being more subtle and sleight of hand, and grounded by someone who has been around the block a time or two.

For me Po’ Boy represents the ‘Every Town’ USA (or whether Occidental) man that continues to lose but maintain some semblance of stable life. But everything and everyone else is deceiving him like people and life in general often do. But above all, he’s fine with all of that. He is noble because of his humility.

We were discussing vaudeville just the other day here, and there is somewhat of a minstrelsy aspect to it, not unlike the role Tom Waits inhabited for much of his own music career. The other thing I like is that beneath its quaintness and charm, there is sometimes a darker undercurrent, as in the lines about his uncle taking him in after his mother died and running a funeral parlour. It’s one of those moments that makes you do a double-take.

Also reflecting the uncharacteristic nature of this song musically, as noted in the Untold Dylan article below, “Dylan gets all the chords that he doesn’t normally use and throws them all in to the mix and then places a melody over the top. Even if you don’t know anything about music, you’ll know this is not normal either for Dylan or for popular music.”

Post-2000, Dylan’s music, especially the instrumentals, was starting to become more in keeping with the tight and more subtle mature band sound, invoking an atmosphere of a cosy, late-night setting. His band on the Never Ending Tour was starting to take shape, with many of the same members playing together for years, and a stripped-back approach where sometimes less is more.

If you’ve been following Dylan’s records and live performances this century, you hear the beginnings of this sound and feel on this 2001 record, Love and Theft, and he really hasn’t departed far from it. It was also the first album he recorded with his Never Ending Tour band.

Prior to this record, Dylan had achieved, as some like to put it, ‘a return to form’ with his critically acclaimed and three-time Grammy Award-winning 1997 album Time Out of Mind, produced by Daniel Lanois. So when Love and Theft was released in 2001, expectations were pretty high, and by almost all accounts it didn’t disappoint, also receiving, like its predecessor, a big thumbs-up from critics and fans alike. The album went on to win the Grammy for Best Contemporary Folk Album.


[Verse 1]
Man comes to the door, I say, “For whom are you looking?”
He says, “Your wife,” I say, “She’s busy in the kitchen cooking”
Poor boy, where you been?
I already told you, won’t tell you again

[Verse 2]
I say, “How much you want for that?” I go into the store
The man says, “Three dollars.” “All right,” I say, “Will you take four?”
Poor boy, never say die
Things will be all right by and by

[Verse 3]
Been working on the mainline, working like the devil
The game is the same, it’s just up on another level
Poor boy, dressed in black
Police at your back

[Verse 4]
Poor boy in a red hot town
Out beyond the twinkling stars
Riding first-class trains, making the rounds
Trying to keep from falling between the cars

[Verse 5]
Othello told Desdemona, “I’m cold, cover me with a blanket
By the way, what happened to that poison wine?”
She said, “I gave it to you, you drank it”
Poor boy, laying them straight
Picking up the cherries falling off the plate

[Verse 6]
Time and love has branded me with its claws
Had to go to Florida dodging them Georgia laws
Poor boy, in the hotel called the Palace of Gloom
Call down to room service, says send up a room

[Verse 7]
My mother was a daughter of a wealthy farmer
My father was a traveling salesman, I never met him
When my mother died, my uncle took me in, he run a funeral parlor
He did a lot of nice things for me and I won’t forget him

[Verse 8]
All I know is that I’m thrilled by your kiss
I don’t know any more than this
Poor boy, picking up sticks
Build you a house out of mortar and bricks

[Verse 9]
Knocking on the door, I say, “Who is it where are you from?”
Man says, “Freddy!” I say, “Freddy who?” He say, “Freddy or not here I come”
Poor boy, ‘neath the stars that shine
Washing them dishes, feeding them swine

References:
1. Po Boy: a walk through the heritage of American culture with Bob Dylan – Untold Dylan