The most interesting songs always take a few listens to reveal themselves. The hard part is getting a person to listen enough for that to happen. Writing a great album requires a balance between songs which pull listeners in, and songs which keep their attention. "Honky Tonk Heroes" is a great example of this sort of thing.
You are pulled in by the title track, and "Low Down Freedom". "Old Five and Dimers Like Me", and "Ain't No God In Mexico" keep you coming back for more. "Willy the Wandering Gypsy" changes your life, and perception of the world.
"Willy the Wandering Gypsy and Me" resembles M.C. Escher's sphere drawings. The spheres where drawn in the first person perspective by Escher himself. Within the reflection of the sphere is Escher, and the world around him. In the one, his eyes reflect back the sphere, reflecting back on itself. In another his hand is shown drawing the painting you are looking at, again reflecting back on itself.
Like Escher's drawing, the song also reflects upon itself in both reality and within the piece itself. The more you listen to it, the more you become convinced that the narrator and Willy are the same person. Within the song the narrator, Willy, and the Gypsy are reflections of each other. Like Escher is an extension of his art, and his art an extension of him. After listening to the song hundreds of times, it becomes obvious that Willy is a manifestation of the narrator, an imaginary friend, a hallucination. He is a character invented by the narrator to describe a corner of his personality.
That's just one angle to look at it.
It gets even more interesting when when you study how this song's reflections bleed into reality. How Willy is a nickname for William, just like Billie. Billie Joe Shaver wrote this song, and he wrote it in the first person. But Willy, is a clear reflection of Billie.
Just like Willy, Shaver was salt of the Texas soil. He was deadset on riding in the big rodeo, but he had to work some side gigs to make cash. Lost two of his fingers when working in a lumber yard, but still managed to played guitar and write songs. As it turns out, the songs where pretty damn good.
Before Waylon Jennings recorded an album of his songs, "Honky Tonk Heroes", Shaver was unknown. Legend has it that Shaver played the song for Jennings backstage at a concert, but then Jennings forgot. In Nashville a few months later, Shaver heard Jennings was drinking with some bikers at a local bar. He confronted Jennings at the bar, and was asked to play the song again. He played "Willy the Wandering Gypsy and Me", "Old Five & Dimers Like Me", and "Aint No God In Mexico". Jennings then agreed to record an entire album of Shavers songs, and this time he kept his word.
Its noteworthy to consider that both times Jennings asked Shaver to play a song, Shaver chose "Willy the Wandering Gypsy and Me". Especially because "Old Five & Dimers Like Me" is undoubtedly a more approachable / sellable song. But, its undeniable that Waylon, just like Shaver is a reflection of "[Willy the Wander Gypsy]".
Although they had different stories, Shaver and Jennings where rolled from the same makings. Jennings was a Blue Texas Northerner that became a performer because he couldn't stomach the idea of working for a living. He had four wives and seven kids, but that never stopped him from living hard. On Honky Tonk Heroes, Jennings delivers the songs with an authenticity that gives Shaver's performances a hard run for their money.
Waylon Jennings has a voice that reverberates the strings of your soul. The performance creates a clarity and intrigue that just doesn't come out when Shaver sings it. Maybe Shaver knew this, and that's why he sought out Jennings. Waylon Jennings' voice is itself a reflection of the song. Its like jamming your head full of figures and angles, but telling us stuff that we already know.