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For the majority of his now-decades-long career in music journalism, Stereogum writer Tom Breihan didn’t consider himself a historian — certainly not like his father, an actual history professor.

“When he retired, his colleagues threw this big party, and one of them made this speech, clowning him for stopping at the side of the road and reading every historical marker… and I was like, ‘Oh, every history professor doesn’t do this?’” he recalls. “He was that big of a history nerd… I was never interested in it at all. I hated it. And when I started writing about music, it was always [about] what’s happening right now, this moment.”

And yet, when Breihan releases his first book (on Nov. 15), it will be that kind of historical compendium. The Number Ones, based on his popular Stereogum column of the same name, dives into songs that have hit No. 1 throughout the 63-year history of the Billboard Hot 100. Despite starting as a series of short-form song reviews, “The Number Ones” has since grown into a set of thoughtful, funny and thoroughly researched essays — zooming in on the tales behind the hits’ creation and release, and zooming out on their larger place in pop history, both in the short-term and the long-term — tracing a non-linear but ultimately fairly comprehensive history of modern pop music in the process. The column’s following has grown along with it, and even expanded to the site’s comment section, where several regular Stereogum readers are contributing their own parallel commentaries, tracking other chart-toppers and notable releases occurring contemporaneously.

While Breihan’s triweekly column will ultimately hit on all 1,143-and-counting No. 1s in chronological order — he started with Ricky Nelson’s inaugural Aug. 1958 Hot 100-topper “Poor Little Fool” in Jan. 2018 and most recently caught up to Eminem’s “Lose Yourself,” which first bested the chart in Nov. 2002 — the book edition of The Number Ones focuses on 20 particularly pivotal No. 1s, ranging from The Beatles to, well, “Black Beatles.” And though a large part of the regular column is Breihan’s own song analysis and personal feelings — including anecdotes from his own life, unfiltered praise and/or criticism, and a whole-number final rating from 1 to 10 (“Poor Little Fool” scored a 3, “Lose Yourself” a 9) — the book version finds him more in that professor mode, telling the stories of the songs and their cultural contexts without devoting as much space to his own personal takes. (“I figure nobody’s buying the book to read about me,” he explains.)

Regardless, both the book and column are fascinating looks at the last six-plus decades of popular music through the prism of Billboard‘s signature songs chart, digging into the nooks and crannies of both the music and the chart itself as the subject requires. Below, Breihan talks with Billboard about the genesis and growth of his column and subsequent accompanying book, while also sharing his feelings about the Hot 100 as it currently stands, and what he thinks (or hopes) the chart might look like in the future. (Ed. note: The conversation has been edited and condensed for clarity.)

When you first started the column in 2018, were you thinking of it as a compendium, a history of pop music? Or were you just thinking, “I’m gonna review these 1,100-whatever songs…”

Not at all. It was just reviewing the songs. I’d been reading Tom Ewing’s column Popular. And it was a really fun read, he’s a great writer. And I was just like, “Well, is there a version of this for the U.S. charts? Is there a Wikipedia page for No. 1 songs?” And obviously there is. And I was sitting there and just being like, “I don’t know what this song is, I don’t know what this song is, this is a gigantic iconic song that everybody knows, and here’s another one that I don’t know what it is…”

And so it was like a “Let me kind of educate myself” type of deal. And in the beginning, I was not writing these long, exhaustive, explainer dealies. That kinda evolved over time. But the column told me what it wanted to be, eventually, I guess. If that’s not the most pretentious thing that anybody’s ever said. 

Did you go in with any kind of Hot 100 knowledge? Obviously, you know about pop music, but knowing about pop music and knowing about the specifics of Hot 100 history are pretty different things. Would you have been able to say, like, what the longest-running No. 1 ever was? Or who had the most No. 1s?

Yeah, yeah, I could’ve said all that, because most of the records were pretty recent, and within my living memory. ‘Coz the way the charts have been collated has changed so many times, and obviously, like, when Mariah Carey comes within shouting distance of The Beatles for the most No. 1s, that becomes a news story. I’ve been living in the music press ecosystem for a long time, and I’ve absorbed a lot of this stuff, both as a fan and as a writer. But actually boring into the nature of the way the chart has changed has opened things up for me, and has just been an interesting way of looking at things, that I hadn’t really done beforehand. 

When you talk about that ecosystem – when do you feel like it became a thing for you and your peers that it was actually common knowledge, and an actual sort of shared language, about what the No. 1 song was that week, what the No. 1 song of all-time was, that sort of thing? 

I don’t know when that became something that all my peers paid attention to. I can say that when I started writing about music, I was into that right away. I started writing for Pitchfork in 2004, and my whole thing at the time was like, “I don’t care about indie rock,” y’know? I did care about indie rock, but I wasn’t interested in writing about it.

I went in there with a chip on my shoulder. I was trying to kind of push my way in as loudly as I could and be like, “Petey Pablo is more interesting than Bright Eyes!” or whatever. And then when I was at The Village Voice, I had to write a column every day. And a lot of the time, when I couldn’t think of anything to write about, it would be like, “Well, let’s talk about what’s in the iTunes top five this week. What’s Flo Rida’s deal? Let’s figure him out.” 

I think working in the tradition of rock criticism, where a lot of sort of underground or trendy stuff gets lionized, I think it’s really interesting and important to keep at least half an eye on what is actually popular at any given moment, and to try to see like what that’s in conversation with, and where that came from, and maybe see where things are going through that. I’ve always thought it’s been part of the job, I guess. 

When you’re signing up to do a column like this, you’re signing up to write over 1,000 mini-columns – and you might not have had a sense of how big they would get, but signing up for 1,000 of anything is a pretty big investment. What gave you the confidence – and maybe even more importantly, what gave your editors the confidence – that you would be willing to stick with this project for years?

I wonder if anybody thought that I would actually stick with it. I don’t know if I thought I would stick with it. I thought it was a fun thing to do, because I was noticing I had dead time in the afternoon, where I wasn’t working on some other column. I don’t know why Scott [Lapatine, Stereogum founder] thought that I could do this. I was pretty much just in Slack one day, like, “Hey, I wanna start doing this. Can I start doing this?” And he was like, “Yeah, sure. You wanna start on Monday?” And I was like, “Uhh…. today. I wanna start today.” And he was like, “Oh. All right… go ahead.”

You know, I’d been working at Stereogum for a while at that point, and whatever – I get bugs up my ass about things, and I get big ideas. And Scott is a really good boss, and he lets me go off when I get fired up about something. 

Was there a particular period of pop history – or maybe even one column specifically – where you remember writing about it and thinking, “OK, now I understand what this column is or should be”? 

There were some songs where I felt like… I need to step up to this song. I really need to work on this song, because the song demands it. Like, “I Heard It Through the Grapevine” was one of those. And “Dancing Queen” was one of those. “These songs are so good, and their stories are so interesting, that I really need to write.” And I haven’t gone back and looked at those columns, but I hope they hold up. Those were the ones where I was really like, “I’m gonna really put my whole foot in. I’m gonna really work as hard as I can. I’m gonna figure out my calendar, and be like, ‘This is what I’m doing today.’” 

I definitely wanted to ask about the most controversial ratings you’ve ever given, either on the high side or the low side. 

Oh man. The one – I think it’s just kind of a little meme for the commenters now — is that I gave “Magic” by Olivia Newton-John a three out of 10. I didn’t have any idea that anybody has any emotional attachment to that song! I don’t think I’d ever heard that song… it just floated right by me. And then the other one that gets brought up a lot: I gave “Penny Lane” a six. I just don’t like that song. Yeah, it’s important, but there’s certain Beatle eras that just don’t – they’re not my bag, necessarily. And so, obviously, I know if I’m gonna give a Beatle song a rating out of 10, like – who am I? But that’s the fun part, you can just be like, “I much prefer ‘Jump’ by Kris Kross.”

Is there an era that you’ve enjoyed writing about the most or the least? 

We’re heading right into the period where I was out of college, and I was like, drunk and out in the world all the time….

But that can be a good thing or a bad thing. 

Oh, it’s a good thing. I love it. Where I was like, “Jesus Christ, I didn’t know Usher was this good!” Everything on the radio sounded awesome to me. That’s like my ‘60s, is the early 2000s. 

And what about the period where you’re like, “Man, don’t want to go back there ever again”? 

I’m a little trepidatious about 2010s stuff. Where it’s a lotta like, EDM and Macklemore and whatnot. I don’t know what that’s going to be like. 

The ‘70s-into-early-‘80s soft-rock era was pretty rough. That was not my favorite. But even when I don’t like the songs, I feel like the stories are a lot of fun. Every one of these songs has a story and most of them are ones that I didn’t know. So when I find them out, it’s fun to get in there and be like, “Oh, that’s who Leo Sayer was!” 

What’s more fun to write, a 10 or a 1? 

A 10 is way more fun to write. I mean, a lot of the 1s – you’re getting into R. Kelly or whatever. Some of that stuff is just depressing. Or like…. I wrote about “One Week” by the Barenaked Ladies. Which is a song that I just can’t stand. And there was some satisfaction in trying to rip a hole in it. But I still had to listen to that song a bunch of times! That wasn’t something that I wanted to do. And so I think you can see me taking out some of that frustration in the writing. 

There has to be one song that you’ve written about, where looking back on it, you just go, “Man, I had nothing to say about that song.” 

Oh, it happens all the time. That’s the challenge. I recently wrote about “Foolish” by Ashanti. Which is a song I never liked, a song I kinda always ignored when it was on the radio — it would just fade into the background. And so the challenge is to be like, “Well first off – how do I write about the song itself in a compelling way? What do I find about it that’s compelling enough to sink my teeth into?”

And also – the stories involved, the people who made it, the currents that brought it up to No. 1. Like, what was happening in the timing? That stuff to me is a lot more interesting a lot of the time than the song itself. And so, when I write about the 14th Mariah Carey No. 1 – it means that I have to get real invested in Mariah Carey’s whole story. I was always interested, but I was never like, super-dialed in. But now because of what she did, and because of the nature of the column, I gotta get real granular: “All right, here’s what was happening with Mariah Carey in the Spring of 1994″ or whatever.

When did you first start thinking about it as a potential book?

I didn’t. My agent, Jack Gernert — who’s younger than me, and was in college here in Charlotte when I moved here — was like, “Let me take you out to coffee. I think this is a book.” And I started thinking about it, and he really held my hand through the process.

I never have to worry about writers’ block, because there always has to be like, five things written right now. But sitting down to write a book proposal, I freaked myself out so hard. But y’know, it’s – I’m lucky that enough people who kinda know what’s going on read the column and were into the idea, that they were able to kinda help me turn it into something. I didn’t know how that would work — it was a lot of, “Who am I to do this?” But I’m super-glad that it’s happening, that I did it, and that I had enough help to really make it work. 

When did you settle on the 20-column format as the guiding principle for the book?

When Jack took me out to coffee, we started talking about it, throwing ideas back and forth. We didn’t come up with a hard number of how many songs it would be, but – driving back to my house that day, I was already putting the list of songs together in my head. And that list changed a little bit, but not that much. And I already had a pretty good idea of what I wanted to write about, and how it would all kind of flow and connect. 

Is there one that you’ve been showing people the table of contents and they go, “Really, that song? I don’t even remember that song,” or “I wouldn’t have expected that song to be one of the most important No. 1s ever”?

Well, when I mention Soulja Boy, people think that’s funny. I think “Rock Your Baby” by George McCrae is a song that a lot of people don’t necessarily know, but in terms of when it came out and what it represented at the time… that’s a song that I’m using as a way into disco, and to talking about disco and why disco was important. And so because of when it came out, and when it hit No. 1, that song is ultimately more important than “Stayin’ Alive” or “I Will Survive” or one of these songs that everybody knows. 

When you look at the Hot 100 charts today, in the streaming era, obviously they’re very different than the years you’ve been writing about – in terms of albums charting 16 songs at a time, and the durations of songs staying on the chart, and so on. How do you compare the charts today to the ones you’ve been writing about for the last couple years? 

I’ve got a friend who’s a college professor, right? And we’re out to dinner a week or two ago, and he’s telling me how one of his getting-to-know-you things with his new students is he has them write down what their favorite music is. And the last time he did it, not only did he not know what most of the music that people wrote down was, but the kids didn’t recognize each others’ favorite music. Everyone has their own thing – they’re into like, Japanese chiptune or whatever the hell. My son listens almost exclusively to British rap cyphers about anime. There’s so many, hyper-niche things that – to the people who are into them, they’re like the biggest thing in the world, and to everybody else, they don’t know that they exist. 

And so I think it’s kinda interesting that old music is more popular than new music now, to an extent. Maybe it’s always been that way, but it really seems like it’s that way now. Like, the Harry Styles song that was No. 1 for a million years this year [“As It Was”]: I couldn’t tell you how that song goes. And certainly that has something to do with me being an old man now, but I think nothing is as culturally present as it used to be. The world itself is so much more fragmented.

So when something like “Running Up That Hill” happens, people get real excited about that. Would’ve been cool if it went all the way to No. 1. But that it went as far as it did is also really cool. And that something like that can happen is really cool too — that something that can just bubble up out of nowhere like that. 

Obviously your column is very successful, but do you think part of that is nostalgia not only for the specific songs you’re writing about, but for the monoculture in general? For the time when a No. 1 song in the country could be known by everyone, and sorta unavoidable to everyone?

Absolutely. I think that that is a huge part of it. And one of the things that’s been interesting in the column lately is that the songs themselves are losing some of the regular readers. So some of the older readers or commenters who have been in it, and reading about the stuff from the ‘70s or ‘80s – they don’t know any Ja Rule songs. They’re like, “What the f–k? Toni Braxton? What?” And y’know, these are songs, as someone who was out in the world at the time, and young — it certainly seems accurate to me that those songs were No. 1. Those songs were all over the place. 

Is the plan to go up to the point where you’re eventually going to be writing about the song that’s No. 1 that very week?

Yeah. I wanna get it there, for sure. I don’t know what I’m gonna do after I get it there… but yeah, I wanna catch up. 

And keeping this in mind, are you now following the Hot 100 a lot more closely? Are there any artists or songs that are kind of on the verge now that have never been No. 1 before, and you’re like, “I kind of hope they get there, because they seem they’d be really interesting to dig into like that?”

Well yeah — like, Dua Lipa has to get there, eventually. I would be shocked if I did not end up writing about her at some point. I’m mad at Lil Baby for releasing all these underwhelming-ass singles. I want him to get there, because I think he’s kind of a generational artist, and I think he should be in the whole historic conversation. But to do that you need that song. 

I’m very curious if “Unholy” makes it. I think it would be cool if it did. [Ed. note: After our conversation, “Unholy” did actually go to No. 1.] But then there’s also like, “Is Morgan Wallen gonna get there? Am I gonna have to deal with that? Am I gonna have to deal with OneRepublic?” And also, what’s gonna catch that Kate Bush wave next? Because that’s not done. It’s gonna happen more. 

You mentioned that you don’t really know what happens after the column ends. I’m sure you must’ve given some thought to something like going through every R&B No. 1, every modern rock No. 1, every No. 1 album – have you ticketed a likely sequel yet? 

Yeah, I’ve thought about rap songs – I think that would be fun – but I feel like maybe I’d lose a whole lot of the audience, and maybe not gain back another one. I think alt-rock would be super-interesting, but it would turn into such a tragedy. It would become just this unrelenting parade of mush. If I did that, I’d have to give myself a real cut-off point, and go, “I’m not gonna get caught up, I’m gonna go as far as – whatever, ‘04, maybe.” Whenever Seether shows up, I’m leaving the party. Like, I’m out. 

I think it would be interesting to look at the albums that have gone diamond. Which is a little bit less of a chronological thing, but – what does it mean when something has that level of sustained interest, where it really really breaks through on an overwhelming level? And there, when you deal with that, you get artists like Shania Twain, who came close, but she never got a Hot 100 No. 1. Led Zeppelin. Stuff like that I could talk about that I don’t get to talk about in the context of this column. 

Do you think a Hot 100 No. 1 is going to mean the same thing a generation from now that it means today?

I think probably right now, most people don’t care if Billie Eilish gets back there, or whatever. She has people who do, but I don’t think that the general public does. But something like the Kate Bush story caught people’s imagination in such a big way. And I think the Steve Lacy story is doing that in a different way at the same time. And now you also have stan armies, which is a new development. And they care very much. They care overwhelmingly, whether or not they can get their people up there. 

So I think right now, there might be more interest in it than at any time that I can remember. I don’t know if that’s gonna sustain necessarily, but I could see it sustaining. I could see it increasing. I hope it does, because it’s just a fun thing to keep track of. And I think the way the internet works, people love numbers, and they love progressions, and they love treating things like sports – and this is a thing people can make bets on, they can make their fantasy drafts or whatever. It’s one more fun running story line that’s available to everybody. 

Also – I don’t know that the general public cared about political polling the way they did before FiveThirtyEight and stuff like that. So anytime you can throw like, numbers and corruptions of justice or whatever into the mix, people get emotionally invested. And that’s all you can ask for from any cultural thing right now. You gotta get people emotionally invested. And the pop charts do that. And I don’t see why they should stop doing that. 

Stereogum belonged to the Billboard-The Hollywood Reporter Media group from December 2016 to Jan. 2020.