I can’t be the only person who finds popular music befuddling.

Not in a “how could anyone like that garbage” sense. Every group has been using that line against the music of anyone they don’t like for the last ten thousand years or more.

But we all have moments where a lyric just stops us dead in our tracks while we try to figure out what the heck someone is singing about.

Case in point: “On the Atchison, Topeka, and The Santa Fe“. The Johnny Mercer song–though I don’t doubt the Judy Garland song has a few headscratchers of its own.

But really: If the schedule is so regular that people use the train as a clock, why does the narrator need to tell Jim to get the rig? Doesn’t Jim know it’s that time already? And how big is that rig–it’s got to hold all the passengers from that “pretty big” list and their luggage. I suppose Jim could make multiple trips, but if everyone is going to Brown’s hotel, is that really the most efficient use of Jim’s time and effort?

Come to think of it, why Brown’s hotel? Is the town big enough to support multiple hotels? If not, why does the narrator specifically say “Brown’s”? Wouldn’t “the” be sufficient? Or if there are multiple hotels in town, why is Brown’s getting all the railroad business–does the singer get a kickback from the hotel for sending Jim’s passengers there instead of spreading the business around? Or does he just dislike the owners of the others?

Maybe these aren’t questions of great cosmic importance, but they’re the kind of thing that keeps me awake at night.

Don’t think this sort of confusion is rare. Consider “A-Tisket, A-Tasket“.

How does the singer know a little girl found the dropped basket, much less that she put it in her pocket? She isn’t reviewing security camera footage; not in the 1940s, certainly. Eyewitnesses? But if she’s found enough of those to confirm the kid grabbed the basket, shoved it in a pocket, and strolled off with it, wouldn’t one of them be able to identify the girl, or at a minimum, tell the singer which direction she went?

Come to that, if the basket was so important, how did she not notice she’d dropped it? Is this some kind of sting operation?

Did girl’s clothes in the 1940s have bigger pockets than girl’s clothes do today? Apparently so. Even if the basket was little, how the heck did the little girl get it in a pocket? And not just get it in, but have it be comfortable enough that she didn’t immediately pull it back out and carry it. It couldn’t have been all that tiny, after all, as the singer implies it was large enough to hold a letter.

This story isn’t adding up. At the beginning of the song, the basket is “green and yellow”, yet just a few verses later, it’s very definitively yellow. In fact, it’s specifically, not green (or red or blue) but yellow. And little.

Wait a second. A letter to her mommy? Where is Mommy that the singer couldn’t just give it to her instead of mailing it? And why is she more concerned about the basket than the letter? Was it a gift from Mommy?

Is it just my imagination, or is this getting awfully deep–and confusing–for a song based on a nursery poem?

And don’t be fooled by the fact that both of these songs are pushing 70. Confusing popular songs are a universal. I’d be willing to bet you can think of an example from your favorite decade with no effort at all.