By Walt Hickey

Welcome to the Numlock Sunday edition.

This week, I spoke to Chris Dalla Riva, author of the new book Uncharted Territory: What Numbers Tell Us about the Biggest Hit Songs and Ourselves.

Chris is a fixture here at Numlock, we’re big fans of his newsletter Can't Get Much Higher and have been eagerly waiting for this book, which tracks the history of music by coasting along the top of the Billboard Hot 100.

The book can be found at Amazon and wherever books are sold, grab a copy!

This interview has been condensed and edited.

Chris Dalla Riva, it is great to have you back on. Especially great this week, because you are finally out with a book that I know you’ve been working on for a very long time, Uncharted Territory. Thanks for coming back on.

Yeah, thrilled to be back, but also thrilled to have the book come out. The book publishing world is one of the only worlds left in the world that moves slow enough where you’re waiting for so long for something to happen.

You have guest-written for Numlock before; you have been a staple of the Sunday editions in the past. You are definitely familiar to the audience at this point because you are doing some of the best music data journalism out there. You’ve been working on this thing for, I feel like, as long as I’ve known you, and it is just great to have it come out finally, man.

Yeah, actually, I met you because I was working on this project. I was trying to track down some data that you’d used at FiveThirtyEight, and you responded to my email with your phone number. You were like, “This is easier to explain over the phone.”

Yeah, I remember I had scraped the radio for months at FiveThirtyEight just to see where it went, and you hit me up with that. I think that you focused some of your energies on the newsletter, and that’s been so fun to follow, but this is truly what you’ve been working at. It is great to get you on finally to talk all about it.

What would you describe this book as? How would you describe it, either to folks who might be familiar with your newsletter or unfamiliar with your newsletter, about what you’re setting out to do with this particular project?

The subtitle, I think, is helpful. It’s What Numbers Tell Us About the Biggest Hit Songs and Ourselves. My typical pitch is that it’s a data-driven history of popular music that I wrote as I spent years listening to every number one hit song in history. You get a balance of music history, data analysis, just random music chart shenanigans. I wrote it over such a very long period of time that you get a little bit of how my life was intersecting with this book over the years as I tried to get it published.

I love the angle on the No.1s being a place to go with, because it gives you a pulse on what’s popular at the time and not necessarily what’s the most influential at the time. You can see there’s a lot of stuff that hit number one at one point or another that have no musical legacy whatsoever, but nevertheless are still interesting. It’s dipping your toe in the stream, right? You can see that a lot of things that we assume about how the music industry works weren’t always the case.

You wrote a little bit about the early transition from big bands to singers as the front-facing people in their operation. That was informed in no small part by what was performing on the charts, but also, I think, labor action, right?

An under-discussed part of music history in the last 100 years is that when thinking of any band now or any musical artist, you almost certainly think of the front person being the singer. But if you go look back at big bands of the 1930s and 1940s, anyone whose name was attached to the band was often not a singer. Some that come to mind are Glenn Miller, the Glenn Miller band. Glenn Miller was a trombone player. Artie Shaw was a clarinet player. If none of these names are familiar to you, that’s okay. But you can ask your grandparents.

Why does this transition happen: suddenly, the lead singer is always getting top billing in a band? There are a bunch of things that contributed to this. One thing I talk about pretty extensively is just the advent of better microphones. If a voice cannot be heard over the roar of an orchestra or a big band, you need a choir of people to sing. It makes the singer less identifiable. As we get better amplification, better microphones, you can get a wider range of vocal styles. Those vocalists can now compete with the sound of a ton of instruments.

At the same time, something you mentioned that I think is a fun bit of history is how music used to be much better organized. They had better labor organization, the same way that Hollywood has much better labor organization than music these days. There still exists a group called the American Federation of Musicians. For two years, they had a strike for a work stoppage, when no new music was being recorded. This was during World War II. You weren’t allowed to strike during World War II.

They were frowned upon very much, it seems, yes.

Yes, even if you were a musician. People were like, “Come on, why are the musicians striking?” There’s a lot of interesting history there. One of the weird loopholes was that singers could not join the American Federation of Musicians. Because of that, some labels would get around the strike by just recording acapella songs or songs with instruments that were not eligible to be membership because they weren’t “serious” enough, like the harmonica. There were weird harmonica songs that were popular at this time. By the time the strike ended, by the time World War II ended, suddenly, singers had a much more prominent role because they were the only ones allowed to perform.

There is tons of weird stuff about this strike. Like, labels backlogged tons of recordings because they knew the strike was coming. “White Christmas,” maybe the best-selling record of all time, was one of those backlogged recordings — recorded in July of 1942 and put out however many months later.

That’s fun. That’s basically why Tom Cruise is in a union but Bad Bunny isn’t?

I guess so. Music and labor have a history that I’m not an expert on. For some reason, musicians have had a much more difficult time organizing. It seemed to be a little bit easier back when there were these big bands that needed to be rolled out to perform in movie theaters or local clubs. You needed a tuba player and a trombone player and a sax player. I guess it was easier for those musicians to organize. Whereas now, things are so scattered and productions can be super small, and you could record something in your bedroom. They never got that level of organization. I think it’s actually hurt artists to some degree because they don’t have the protections that the film industry does.

Because you’re able to just coast along at the top of the charts throughout basically the century, you’re able to get lots of different interweaving stories of labor and also legal disputes/legal outcomes, as well as this technological evolution. What are some of the ways that technology has informed how the music that we listen to changes or evolves over time? Or even some of the litigation that we have seen over the course of the century of musical creation. It just seems like it’s a really fun way to track some of these bigger trends that we don’t even know are really trends.

Yeah, totally. I think one of the key themes of the book is that musical evolution is often downstream from technological innovation, which has a nice little ring to it. But in general, there’s this idea that creativity is being struck by the muse, and you create something. Whereas in reality, there are usually physical constraints or technological constraints that shape the art that we make. One of the most basic examples is the length of songs. From the ’40s up till the early, mid-60s, the pop song sits around 2.5 to three minutes. The reason for this is that vinyl singles could literally not hold more sound without degrading, which is completely backwards from the idea that there was an artist who chose to write a 2.5-minute song.

I was like, “Well, you had to work within the constraint.” Then technology gets better, singles start to get longer. During the disco era, they actually made bigger discs to put out these long dance mixes. The single sat around like 3.5 to 4.5 minutes for decades until about 10 years ago, when it started to shorten again. People typically point to music streaming for this reason, because artists are paid if a song is listened to for more than 30 seconds, so it’s really just a volume game. If you have a 14 minute song that someone listens to one time, they get paid once. But if I listen to a two-minute song seven times (which is again, the same amount of time spent listening), I will be paid out seven times. There is this financial incentive to shorten songs.

I don’t think artists are sitting in the studio thinking about this constantly. But what I see, what I saw again and again, is that artists were rational beings to some degree and would work within the constraints that they were given. They would usually push against those constraints. That’s wh...