Bill Callahan Gives His Take on Every No. 1 Song of 2019 So Far, From ‘Thank U, Next’ to ‘Old Town Road’

In the midst of stumping for his sprawling, pastoral new double album Shepherd in a Sheepskin Vest, the indie folk artist Bill Callahan name-dropped Ariana Grande, praising her for her ability to turn her personal life into art. “She’s making a story of herself,” he told Pitchfork last May. ”Very self-referential.” In his own way, maybe he can relate.

Callahan is nowhere near as splashy as the mainstream Grande, but on Shepherd, he candidly opens up on a smaller scale: about daily minutiae, parental loss and his relationship with his wife and young son.

As a cult artist who seems to whittle songs from ancient redwood, one could assume Callahan would be indifferent or hostile to pop conventions. But in indie as in the mainstream, honesty and innovation prevail, and as it turns out, he finds a lot to love about modern-day hitmakers like Grande and Lil Nas X, who, in his words, “break the rules” of what a pop song can be.

For almost 30 years, Callahan has made music on his own terms. He made noisy, challenging records as Smog in the 1990s and early 2000s before switching to his own name in 2007, recording mostly for the Chicago indie label Drag City. His voice is a resonant bullhorn; he writes with severe economy. One lyric from Shepherd in a Sheepskin Vest: “I got married/ To my wife/ She’s lovely.” “I like to pare away words because I don’t want to waste anybody’s time,” he told Pitchfork in 2013.

As the polar opposite of a pop star, Callahan has a fresh perspective on the Hot 100 landscape. With his co-signing of Ariana Grande in mind, we asked him for his opinion on every No. 1 hit of 2019 so far.

Ariana Grande, “Thank U, Next”

You’ve mentioned your admiration for Grande. Do you find her self-referentiality rare in pop today?

It’s the norm. But she does it with grace and a wink. Not just bragging, which I enjoy, too. And I think what I meant by that more specifically is that she’s not just riding on tragedy and public pain like a lot of artists. She’s actually interfacing with it, not just singing with a picture of it.

She’s reflecting on her breakups so graciously. More than most twenty-somethings in the public eye would.

She’s a smartie.

Halsey, “Without Me”

Here, Halsey is singing about feeling taken advantage of. Have you ever written from that perspective?

No, I haven’t had any issues with my teeth lately. Oh, sorry, I thought I was at the dentist. I probably have written from this perspective. But being taken advantage of is your own fault in the end.

Post Malone and Swae Lee, “Sunflower”

“Sunflower” was recorded for the soundtrack to the movie Spider Man: Into the Spider-Verse. Anything resonate with you about this one?

The grit of the vocals is so polished up. It’s new to me in that way. I’d like to have produced this for these guys. Raw, it would bang!

Like the last two No. 1s, this one has dreamy, abstracted production. Why do you think that style is in vogue right now?

We are transitioning in music, much in the same way that gender and sexual and political stuff is transitioning. Ambient music is a placeholder in life and in music. It’s neither here nor there. Maybe that is where we are supposed to be in music and sexuality and politics.

Ariana Grande, “7 Rings”

This is a heel-turn from “Thank U, Next.” Here, Ari’s flexing her material wealth.

I took it more as empowerment through friendship and loyalty. And poking fun at her own glamour. I think the song works as a classic “ladies’ night out” or “Who needs men?” song. And it’s mystical, the title alone.

What do you think of her interpolation of “My Favorite Things” from The Sound of Music?

“My Favorite Things” is a song I treasure. The Coltrane version I’ve been listening to in various forms over the years was just prepping me internally for this song. Laying a blueprint to accept this deeply into the mystic heart.

Lady Gaga and Bradley Cooper, “Shallow”

When and where did you last hear “Shallow”? It’s been ubiquitous this year.

Maybe I’m lucky; I first heard it when you asked me to listen.

I thought we were further than ever from a “grizzled songwriter” space in pop, but here we are.

It does sound prehistoric compared to the rest of these numbers. People forget how pleasant it is to live in a non-digital world.

Jonas Brothers, “Sucker”

In a year of mostly left-field No. 1s so far, “Sucker” has a very straightforward approach. Thoughts?

I like a production like this where you can hear and recreate exactly what they did. But it’s not breaking any rules like a good pop song needs to. I tried to play it for my four-year-old, but he wanted to hear Busy Signal instead.

Lil Nas X feat. Billy Ray Cyrus, “Old Town Road”

Why do you think this song about country living is taking over the world right now?

I think it has to do with the ambient transition I mentioned earlier. It extends to culture. Music has always been about collaging and sampling, you just used to have to perform the sample every time.

I think a lot about cultural appropriation. Most music originated in black culture. Joni Mitchell fucked me up a few years ago when I was writing my new album and I read her saying, “Why is everyone trying to sing like a black person?” I took it to heart.

The only way I can look at it is an ambient merging. In thousands of years, black and white culture may have merged, I don’t know.

There’s a video going around of elementary schoolers losing their minds to “Old Town Road.” What do you think it communicates to children?

I think children just see and feel the union of souls that could someday be ours, so they get excited.

What about Lil Nas X’s staying power? Does he have another No. 1 in him?

This one broke the rules. Which, as I said earlier, is needed. I think he can do it again.

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