This column is called REWIND because, for its first year, I listed my top five songs from every year since 1967. It was a good project and I can’t believe I finished it. I made a few mistakes, but largely stand by all my choices.

I bring it up because when I’m feeling uncreative, I consider going backward from 1967. The problems with that idea are twofold. First, the farther you go into the past, the less music there is that’s relatable to modern tastes. Not none of course, there’s always been at least some good music and there always will be, but not only is time a filter but, also, changing tastes. That means fewer people will read it.

Second, the late ’60s are when I start being extremely, probably too familiar with music. I know a lot of the early ’60s and even late ’50s but my obsessive hoarding of knowledge starts around 1967. That means to go before that, I’d have to do research rather than just fact-check myself. And that sounds like a lot of work.

How major are those problems? Well, let’s find out! Let’s go back into the distant past and see what music was like. Since Pearl Harbor Day was this past Thursday—read a history book—let’s look up some of the most popular songs in 1941 and see what we have to work with here.

Glenn Miller featuring Tex Beneke and the Four Modernaires — “Chattanooga Choo Choo”

First off, did I use “featuring” rather than the more traditional “with” because I think it’s funny to refer to bands from 80 years ago like they’re a rap collab that just dropped? Yes. Obviously.

We start here because this was the top song on the Billboard charts on Dec. 7, 1941, the day Pearl Harbor was attacked. It topped the charts for nine weeks in late 1941 and early 1942, propelled by the popularity of movie “Sun Valley Serenade,” in which it was featured. I guess some things don’t change.

Wikipedia says it was the first song to get a gold record, but from its publisher rather than the RIAA. It sold 1.2 million copies, which is actually a whole lot—Taylor Swift’s Midnights only sold about 2.5 million, but I don’t think Glenn Miller fans had Spotify as an option back then.

This recording of “Chattanooga Choo Choo” is a big band song. Lots of horns. Not bad, but the ’90s swing revival kinda ruined swing music for me as a concept. Also the name is kinda dumb. Let’s see what else we’ve got.

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Artie Shaw and His Orchestra — “Frenesi”

“Chattanooga Choo Choo” happened to coincide with the reason I picked 1941 specifically, but let’s go with the most popular, defined as the one that spent the most weeks on top of the charts. That happens to be “Frenesi,” which spent the first 10 weeks at no. 1, then another week after that. It had 13 weeks in total if you include 1940.

I’m not exactly a jazz fan—again, I’m actually doing research for this one—but apparently this is a jazz standard. The original writer was Mexican composer and marimba artist Alberto Domínguez Borrás in 1939 and, as was custom at the time, performed by literally everyone for decades after that. Of course the most popular version was this and not the original by the Latino guy.

We should bring back standards as an accepted and encouraged thing. When Taylor Swift released “Anti-Hero,” every other band or singer should have done their own version, then kept it up for two or three years. It’s probably still legal! I think! I haven’t checked because I can’t play any instruments or sing, so I’m not gonna be the one sued.

“Frenesi” is probably good! As of right now I’ve heard two songs I know are from 1941 and I’m still pretty sure it wouldn’t make my top five.

Andrews Sisters — “Boogie Woogie Bugle Boy”

OK, let’s ditch the charts and look over the releases that stood the test of time rather than the ones popular when they were new.

The first thing that jumped out is “Boogie Woogie Bugle Boy.” I actually, legitimately enjoy this song! I assumed it came out during WWII since that’s when the pro-military stuff was hot, but no, it’s from January 1941. Pearl Harbor wasn’t bombed until Dec. 7. I guess it was for an Abbott and Costello movie about the 1940 Selective Service Act. The Nazis had conquered France by then, I guess they knew it was coming.

As an aside, it was recorded on Jan. 2 and released on Jan. 20. That’s amazing. Taylor Swift and Jack Antonoff wrote Midnights in late 2021 when their respective partners were filming a movie in Panama, and it was announced in August, which means by its October release the process had already taken a year and probably not released for a couple months after it was done. Granted, that was a whole album rather than one song, but the difference in scale is still staggering.

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Gene Autry — “You Are My Sunshine”

So far, I’ve been looking at the main Billboard chart. Back then they divided it in three, which is less than the current 450 or so genres and sub-genres that get their own charts, but… not better.

This was the top song of the year on the country chart. Except it wasn’t called the “country chart.” Back then, the categories were the main chart that didn’t have a name—presumably that was just music—along with Hillbilly and Race. I am not making that up. I wish they would have kept the name to be honest, just so we can say Taylor Swift started her career as a hillbilly before crossing over to normal music.

Anyway, this version of the country standard by the Singing Cowboy himself was the top record on the hillbilly chart. It’s a great version of a great song. And it has special meaning to my girlfriend, so obviously this would make the list.

Billie Holiday — “God Bless the Child”

I misspoke. They didn’t rename the chart to “Race” until the mid-’40s, and it didn’t begin as a separate chart until late 1942. That makes it difficult to find any Black artists other than Duke Ellington in 1941. Also, the chart started as the Harlem Hit Parade, which might actually be more patronizing ,somehow.

Anyway, this may come as a shock to anyone who’s been locked in a basement for their entire life, but Black music history hasn’t been as well-documented as white music. It took me longer to piece together a list of songs by Black artists published in 1941 than it did for the rest of this column combined. If I had more time, it would take a trip to the library at least. But then I saw Billie Holiday dropped this song.

The lack of history is ironic because just three years later, in 1944, musical pioneer Sister Rosetta Tharpe would play an electric guitar on one of those race records and invent what would become rock and roll, which went on to not only make swing and big band music obsolete but completely change hillbilly music as well. Even though the popularity of rock may be fading, the electric guitar is a default instrument. Most of the songs on Midnights have an electric guitar, even if it’s just part of the overall sound rather than a main instrument.

I’m calling it hillbilly music forever, by the way. You can’t stop me.

So what’s my conclusion for this column’s premise? Well, going back to the ’40s or earlier to pick my five favorite songs would be quite the challenge, because the racists of the time didn’t bother making a comprehensive record of the best stuff. But that’s also probably a reason to put in the work and do it. I mean, nobody may read it, but I could have used a few well-researched lists.

Follow publisher Daniel J. Willis and send column ideas to him at @bayareadata.press on BlueSky. (He has some invites if you ask nicely).