Numlock Sunday: Chris Dalla Riva explores Uncharted Territory

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 where a lot of great art comes out of.

Even new mediums are offering new opportunities. You wrote a little bit about MTV and how that really changed a lot of what was able to be successful at the time. You had new types of acts that were able to really start competing there, and other acts that just weren’t. Do you wanna speak a little bit about like what video did?

Yeah, video certainly changed the game. There were artists who had visual presences earlier. The Beatles had a very visual presence. I think part of their success is tied to the fact that television was becoming a thing, and mass media was really becoming a thing. However, we associate musicians with visuals so much these days. That really emerged in the 1980s, where you needed your visual concepts to be as strong, if not stronger than, your musical concepts. I think because of that, you start seeing some artists break through who I don’t think are considered great musicians.

I always sadly point to the song, “Hey Mickey” by Tony Basil. If it’s your favorite song, sorry. I don’t think it’s a masterful musical creation, but it had this fun music video where she’s dressed up as a cheerleader. A lot of that song’s success was just the fact that MTV was willing to put that in heavy rotation because it was a fun video to watch. We live in the shadow of that era where visuals matter just as much as anything else.

When you think about the most popular artists, outside of maybe a handful, you think of their visual concepts. You think of what Beyoncé looks like, what her videos are like, same with Taylor Swift, as much as you think about their music. That really reshaped our relationship with popular music. We expect to know what artists look like. It’s odd to think about that; it really wasn’t a thing decades before. You could be a fan of an artist and not really know what they look like. How would you know? Maybe you saw them in a magazine. Maybe you caught them on one television show. The idea that we have access to what everyone looks like is a pretty new phenomenon.

That’s fun. It’s just so interesting to see how a simple change, whether it’s today an algorithm or then a medium of distribution, can just have material impacts on the popularity of British synth music in America.

Yeah, that’s the perfect example. There’s a great book called I Want My MTV, and it’s an oral history of MTV. They talked to one of the founders. Early MTV would play, as you’re saying, all these British new wave acts. Think A Flock of Seagulls, Duran Duran or even someone like U2. They asked the founder, “Why were you playing so many British artists on early MTV?” He was like, “For some reason, British artists happened to make music videos. And there were about 200 music videos in existence. We had to fill 24 hours of programming.” A Flock of Seagulls was gonna get played a bunch of times just because they happened to make music videos.

It is a weird thing. Why would anyone make a music video if there was nowhere to really play them? I don’t know why specifically the British had more videos, but there were occasional times where television shows might show a video.

They do love that over there, like Top of the Pops. I can see why.

Music and television have always been connected. You even think Saturday Night Live still has musical acts. Back then, say your label didn’t wanna send you out to Britain to go on Top of the Pops. Maybe they would send a video of you instead. There were videos that would float around on these variety shows, and some early videos were just concert footage. It was like, it was a chicken or the egg thing. Once some people had success on MTV, everyone started producing videos. MTV somehow pulled off the miracle of convincing labels that they needed to make videos and that they needed to front the cost for that. Then they had to give MTV the video for free. I don’t know how MTV managed to do that.

Well, all of Gen X can’t be wrong. If you do wanna get it out there, you do have to get it out there. One really fun recurring thing in the book — which again, like I really enjoyed. I think it’s a phenomenal work. I think it’s a great history. I’m telling stories that I learned in your book to everybody. It is a really fun read in that regard, I wanna say.

I do love how you occasionally clock a genre that really only exists briefly. There’s one that always goes around for like the strangest things to hit number one, like the Ballad of the Green Berets. I think like there’s a Star Wars disco track that I definitely have on vinyl at home about that. You wrote a lot about like teen tragedy songs. What are some of the fascinating like brief trends that only made a small splash and that all of us have forgotten ever existed, but nevertheless achieve some measure of immortality?

Yeah, the teen tragedy song is a good one. That actually inspired the writing of this whole book because I got 50 No. 1s, and I was like, “Why are there so many number ones about teenagers dying? That’s a little weird.” And then I did a little digging and tried to piece together why that was. The teenage tragedy song, late ’50s, early ’60s, there are all of these songs about two teenagers in love, usually high schoolers. One tragically dies often in a car crash, and the other is very sad and maybe says that they’ll reunite again one day in the afterlife. Some of the big ones are “Leader of the Pack” by the Shangri-Las and “Teen Angel” by Mark Dinning.

It’s a very weird blip in popular music history. I won’t say it has cast a long shadow, but there are some occasional people who pull from that tradition. The craziest teen tragedy song ever was “Bat Outta Hell” by Meatloaf, in which Jim Steinman tried to write a nine-minute motorcycle crash song. I think that’s a really interesting one.

Disco: bizarre in the amount of people that made disco songs. I really came to like disco and the best disco music, I’m like, “These are the greatest sounds that have ever been recorded.” But it got so big and so popular that everyone felt the need to record disco songs.

Not everything is “I Feel Love,” right?

No, most things are not. It strikes me that this happened with disco, but has not happened with other genres. Frank Sinatra recorded disco songs. Basically, every television theme song got a disco remix. I Love Lucy had a disco remix. The Rocky theme song had a disco remix.

What? I’m sorry, Frank Sinatra did a disco song? Is it good?

It’s not good. It’s “Night and Day” over a disco beat. And it’s not clear to me if they just remixed it or if he actually recut the vocal because I just cannot imagine him doing that. In the mid-60s, there was a nun who topped the charts, The Singing Nun with a song called “Dominique.” Of course, during the disco era, it was remixed as a disco song. There are examples of this where people went sort of disco. The Rolling Stones record “Miss You” and it has the disco beat, or Pink Floyd does “Another Brick in the Wall” or Queen does “Another One Bites the Dust.”

Everyone was gonna give it a try. There was so much money being made in the disco world at the time. You can always find some artists you would never think would do a disco song probably tried. They probably gave it their best.

That’s great. It’s just fun because the things that hit number one for a week don’t necessarily have to be good. They just have to be popular for like a week. Even the construction of the Top 40 chart, which you get into in the book, isn’t exactly science. A lot of times, it’s a little bit of intuition. It’s a lot of what’s selling and what’s selling where specifically. It is a little bit woo woo, right?

Yeah, definitely. The goal of this chart is “What’s the most popular song in America in a given week?” Back in the day, that meant what were people buying? What were people listening to on the radio? What were people spinning in jukeboxes? Today, most music is done on streaming. It’s consumption-based, rather than sales-based. So the chart’s the same in name only, but it’s really measuring very different things. The equivalent would be if we knew after you purchased your copy of “I Feel Love,” how many times did you actually play it at home? You could have purchased it, went home and never played it again. Something like that would not register on the charts these days.

I respect the people at Billboard because they have an impossible task. It’s like “We’re gonna take all the information and we’re going to boil it down into choosing or measuring what the most popular song is.” It’s an impossible task to some degree.

I have watched the evolution of the chart, and I go back and forth on whether they have given up on actually trying to rank stuff or if they are just ranking things in a different way. I think that the apples-to-apples between the era stuff is just so hard to do.

One thing I really enjoyed about your book, in particular, is that it’s not a story of why these songs are the best. It’s a story of why these songs were popular at the time, just dipping the toe into the river of human sound. One thing that I’ll ask as you wrap: as you were going through these eras, who did you hear a lot more of than you thought? Who did you hear a lot less than you expected?

I joked with some people that if you just looked at the top of the charts, the greatest rock band of the 1970s is either Grand Funk Railroad or Three Dog Night because they both had three number one hits, and many other bands in the classic rock canon have none. Led Zeppelin does not really exist on the pop chart, the singles chart. Led Zeppelin really only put out albums. The Eagles were also big during the ’70s on the music charts. But Three Dog Night, they’re the legends.

There are tons of people that I didn’t realize how much I would see of them. Someone like Lionel Richie and Phil Collins, of course, they’re tremendously popular, but they were so popular. Phil Collins was popular at the height of the bald pop star era, which I think is a thing of the past. You had multiple bald men who were regularly topping the charts in the mid-80s. You see a ton of Phil Collins, more than I was expecting, even though I know he’s very popular.

Who don’t you see a ton of? Sometimes you don’t see people until a bit later in their careers. This is actually an interesting phenomenon. Artists do not score a number one hit during their most critically acclaimed period, and then a decade later, they do. For example, Cheap Trick. They have a number one hit, but it’s at the end of the ’80s song called “The Flame.” Whereas if you hear Cheap Trick on the radio, it’s probably their live album from the 1970s. This is a phenomenon you see again and again. Some old timer will get their number one much later in their career. Tina Turner gets her number one when she’s probably in her 40s. It’s always interesting to see that.

There are also some artists where I feel like there’s a divergence between what their most popular songs are these days and what was topping the charts. Elton John is a good example there. “Benny and the Jets” was a number one hit, still a tremendously popular song. But he’s got a lot of weird No. 1s that I don’t think have as much street cred these days. He has a song called “Island Girl.” Did not age like fine wine. I don’t even think he plays it live anymore because it’s considered somewhat racially insensitive. But it was a No. 1 hit at the time. “Philadelphia Freedom” is another one by Elton John. I feel like when people think of the Elton John catalog, it’s probably not the first song that comes to mind. But it was a No. 1 hit, huge smash. His cover of “Lucy in the Sky with Diamonds” was a No. 1. Elton John has been very popular throughout the decades, but I feel like the reasons he’s been popular have changed.

People have just gravitated towards different songs as time has gone on. You get distortions at the top of the charts. But I think, as you mentioned, it provides a good sample of what was actually popular. You have the good, the bad, and the ugly. Whereas if you look at some other sources, people are just gonna be like, “Oh, listen to these records. These are the best records.” In reality, the bad records are important, too.

Yeah, bad records are great. They’re at least interesting. I imagine also some of this process must have been missing out on a lot of interesting music because one song was just dominating the charts. Were there any songs in particular that come to mind that wooled the roost for potentially a little bit too long?

Yeah, the quintessential example is the “Macarena” in the ‘90s.

Oh, no!

I think it was No. 1 for 13 weeks.

Christ!

There’s a great clip of people at the Democratic National Convention and ’96 dancing the “Macarena.” It’s so bad. Yeah, so a very popular song. There are tons of stuff that gets stuck behind it. There’s a great No.1 hit in the ’90s called “I Love You Always Forever.” It’s a very nice song by Donna Lewis. It’s stuck at No. 2 because it just happened to be popular during the “Macarena’s” very long run. Y

Your life’s work, your greatest accomplishment, being stymied by the “Macarena” feels like a level of creative hell that I have never envisioned before.

Yeah, there are other artists who got unlucky. Bruce Springsteen never performed a No. 1 hit. He wrote a No.1 hit for another artist. His closest was “Dancing in the Dark” got to No. 2, but that was also when Prince released “When Doves Cry,” so it’s a tough, tough week. Bob Dylan, similar thing. He wrote a No. 1 hit, but he only ever got to No. 2. I think he got to No. 2 twice. Once, he got stuck behind “Help” by the Beatles, and another time he got stuck behind “Monday Monday” by the Mamas and the Papas.

This is another thing when I talk about the charts. There could be many fewer units sold in a given week, or there could be many more units sold. There’s a lot of luck involved if you’re gonna go all the way to No. 1. You could be Bruce Springsteen: you release the biggest record of your life, and Prince also releases the biggest record of his life at the exact same time.

Incredible. So again, I have read the book. I really, really like it. People are doubtlessly familiar with the newsletter at this point, but I am also a big fan and booster of that. But I guess I’ll just throw it to you. Where can folks find the book, and where can folks find you?

Yeah, you can find me, Chris Dalla Riva, basically on every social media platform under cdallarivamusic. I’m most active on TikTok and Instagram. The book, Uncharted Territory: What Numbers Tell Us About the Biggest Hit Songs and Ourselves, should be available from every major retailer online. Amazon, Barnes & Noble, Walmart, Booklist, all that good stuff. Not available physically in stores, so definitely order it online.

Like I said, I spent years listening to every No. 1 hit in history, built a giant data set about all those songs and used that to write a data-driven history of popular music from 1958 to basically 2025. So go pick up a copy, buy one for your mother for Christmas. Or your father, I don’t discriminate. Yeah, check it out. I’m hoping people enjoy it, and I’m really excited to finally get it out in the world. It’s been a long, circuitous journey to get it published.

It’s a really fun read, and I wish it nothing but the best. And yeah, congrats, thanks for coming on.

Yeah, thanks for having me.

Edited by Crystal Wang

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