The Pilgrim tells the story of a man from Marty Stuart's hometown of Philadelphia, Mississippi and this track is from the point of view of a crow observing the town's nightlife. Stuart told the story of the song to American Songwriter magazine: "I was riding through the West. I think we were pulling off of the interstate and we pulled off on Route 66 somewhere just to get fuel in the bus. It was like one of the places, it looked like a ghost town. There was just a few locals around."

"But I happened to look up. And there was a crow sitting on the electrical line. And I couldn't take my eyes off him. I've always been fascinated by crows, I've always loved crows. Bus as people would come and go, the few people that there were, that crow never left. He kept hanging out. And I thought, 'The Observations Of A Crow.' And it was that simple but it was an occurrence that came to me on Route 66 somewhere."

There has been a number of discussions on message boards concerning the melodic similarities between this song, and Bob Dylan's "Things Have Changed," which was recorded shortly afterwards. Stuart told American Songwriter magazine there is a reason for the resemblance, due to one night when he hung out with Dylan.

"I took him to my warehouse to see all the country music treasures I have," Stuart said. "Bob said, 'Hey, I like that 'Crow' song. I might borrow something out of that.' I said, 'Well, I probably borrowed it from you in the first place. Go ahead."

Here are some crow fun facts from The Encyclopedia of Trivia:

Crows have different warning calls depending on the type of predator they are warning their fellow crows about.

Crows recognize human faces and can hold grudges.

"As the crow flies" is an idiom for the shortest route between two points. It is actually the rook that flies straight to its destination, rather than the crow, but the two black birds are often identified with each other.

When crows drop stones into water to make food more accessible, they display the reasoning skills of children aged 5-7.