How You Get the World: Reflections on Taylor Swift, Pt. 4

Part 4: Imagining a world without "Teardrops"

Keeps me wishin’ on a wishin’ star

What if there weren’t museum exhibits devoted to Taylor Swift?

All installments: Part 1 // Part 2 // Part 3 // Part 4 // Part 5 // Part 6 // Postscript 1

There’s a fairly well-established story that goes like this: Taylor Swift started as a country artist, and got so huge in country music that it made a dent in the pop charts. Country sustained her for a few years until she started going “pop,” at which point she was pushed out of the genre (unclear exactly who’s doing the pushing) and settled on merely being the biggest pop star of one going on two generations.

I quibble with the timing of the standard story, which puts the move away from country sometime around 2012 — I think Taylor Swift had basically walked away from country the second “Love Story” came out. But I tend to believe some version of this story is true. It’s undeniable that country audiences comprised a foundation on which Taylor Swift built a more general, young audience through 2007 that exploded in 2008. It’s also easy enough to show that country media was skeptical of Swift: in fact this skepticism was built into the release strategy of her debut:

Whether anyone would accept Ms. Swift’s sound was an open question. “We felt it wasn’t likely that country radio would embrace it unless we had a story,” [Scott] Borchetta [president of Big Machine] said, so Ms. Swift made a series of biographical shorts to air on the GAC (Great American Country) cable network. Then came “Tim McGraw,” Ms. Swift’s canny first single, named after the country superstar. (In the lyrics Mr. McGraw is the singer of a special song she and a boy share.) “We put that out deliberately, so people would ask, who’s this new artist with a song called ‘Tim McGraw’?” said Mr. Borchetta, who likened its reception to that of “a grenade in a still pond.”

That’s from a Jon Caramanica profile in the New York Times on the eve of the release of Fearless in November 2008.

These profiles, which were numerous at the time and mostly tell a similar story, all support the mythology of the Taylor Swift we’ve been living with for 15 years, the all-purpose pop star for whom country was an important pit stop on the road to inexorable world domination. That’s a story that’s easy to write in hindsight, because it is, in fact, what happened. Taylor Swift worked. And it was clear that Taylor Swift had “worked” a month before her second album came out. When an exec at Country Music Television says in that Caramanica piece “it’s as if Taylor has kind of willed herself into being,” he’s right.

But I still wonder if it had to happen that way. Could anything at all have happened between 2006 and 2008, including modest country chart success with no pop crossover, and we’d still have Taylor Swift as we now know her snap into place on the pop charts with the release of “Love Story” in September 2008? Maybe. But at the same time, it all felt much more fragile in 2006 and 2007 — Taylor Swift was in some ways a wild bet that had almost no chance of paying off, until it did.

And the element of that uncertainty in the interregnum between her first and second album that I find the most puzzling is that by all appearances, it was “Teardrops on My Guitar” more than any other song that ultimately paved the way for her breakthrough.¹

When you look at all those late 2008 profiles and appearances from the eve of the Fearless release, you can clearly see the dam of superstardom about to burst. “Love Story” is the deluge that finally brings down the walls. I see absolutely no room for counterfactual history after “Love Story” hits the way it hits— Taylor Swift as we know her today is fully formed and indestructible from that point. By November of 2008 it is easier to imagine the end of the world than the end of Taylor Swift.

But I want to account for how the pressure built up, swelled to the point that “Love Story” could so obviously hit hard, could usher in what looks to be a 20-year unabated imperial phase (more on whether that’s the accurate term in a future post). The journey of “Teardrops on My Guitar” is worth tracking carefully, because before “Teardrops,” Taylor Swift was really just a promising country radio star with glimmers of maybe eventually crossing over like Carrie Underwood if she was lucky.

Initial country radio adds for “Teardrops on My Guitar” started in February 2007. At that time there was zero indication that Taylor Swift was poised to cross over to the pop charts. If you look back to a normie-ish, teenybopper airplay-focused message board like Pulse, not everyone thought this was a great release strategy: a ballad as the second single?

Pulse Music Board, January 2007

“Teardrops” then had a slow but steady crawl up the country charts: entered at #46 in February, got up to #20 by May, cracked the top ten in July, and finally peaked at #2 on the country charts in August. Around that time, on August 21, Taylor Swift performed the song on America’s Got Talent, singing it as a duet with a finalist. Taylor looks ready for the world, but the world doesn’t feel quite ready for her.

If the movement up the country charts was slow and steady, its position on the pop charts was much more wobbly. It entered at #93 in March 2007, only the second-biggest country crossover of its debut week, after Billy Currington’s “Good Directions” at #91. By August it had been hovering around the edge of the top 40 for ages, occasionally dipping into the 30s and peaking at #33 on August 11. Then the song vanished from the charts for three months between September and December, when Big Machine released a “pop remix” that got the song back in the pop charts, at #44 on December 15, 2007. From there it rose to its final peak at #13 in March, 2008, almost a year to the day after its initial pop crossover.²

It’s unclear to me what role Radio Disney’s embrace of “Teardrops” sometime in the late fall of 2007 plays in this story. I don’t have great data for when they started playing it, or why. I’m not even sure whether the version they played was the original or the pop remix. But by the end of 2007, “Teardrops” was regularly showing up in the listener-voted top ten week after week, during a period when Radio Disney had no reason to play any Taylor Swift songs. In 2007, Radio Disney was at the height of its control over its own charts, with plenty of content from Disney-owned Hollywood Records artists and soundtrack songs from its Disney Channel shows and movies.

By December of 2007, “Teardrops” had transformed Taylor Swift into a fixture on the pop charts and the Radio Disney charts. And that groundswell is where the initial Taylor Swift cascade came from; it was the catalyst for the momentum that would make her huge impact with Fearless feel like a foregone conclusion by the time “Love Story” was released in the fall of 2008. Did the kids make “Teardrops” happen, or did “Teardrops” make the kids happen? Hard to say.

I wonder about one thing, though, the way you might wonder about key battles that turned the tide of a war somehow going the other way: could Taylor Swift have been stopped if Reply #10 on the Pulse Music Board on Jan 17, 2007 at 1:43pm was correct? What would have happened if “Teardrops” had flopped? What if Billy Currington continued to slightly outpace Taylor Swift in the country-to-pop crossover competition, worthy of a minor footnote in a Billboard write-up that’s mostly about Fergie, until both songs bottomed out a month or two later after they’d peered over the fence at the rest of the top 40? (Currington’s song peaked at #42.)

In that world, I think “Our Song” does a little better on the country charts but similarly stalls out around #40 on the pop charts if not lower, and “Our Song” almost certainly never gets a year-long foothold in Radio Disney’s 6-14 demographic for no obvious reason while Disney has ten to twenty other vertically-integrated stars to look out for.³

Taylor Swift was certainly savvy, and in interviews she (and credulous profile-writers) made a lot in 2007 and 2008 of her obsessive focus on fan communication online. But there were a lot of savvy MySpacers building huge parasocial youth fanbases and releasing pretty good music in the mid-aughts that failed to comparably take the world by storm.⁴ (That was arguably the mid-aughts’ whole deal.) And there’s no great way to go back to build those alternate histories or see how popular some of those folks maybe almost were, since MySpace imploded catastrophically and has already been memory-holed more completely than much older web forums that still leave meaningful archival traces.

I can only give you what I experienced. For instance, I was so convinced that Brie Larson was going to put out an indie-pop masterpiece circa 2008 that I conducted my only ever celebrity interview with her. (I think I was basically right about Brie Larson being a genius, and she still has millions of followers, all built on the savvy of her online presence going back 15 years.) Skye Sweetnam was good enough at MySpace blogging that I got her an honorable mention in one of the Da Capo Best Music Writing series. But Brie Larson never made another album and Skye Sweetnam got jerked around by Capitol until they finally let her put out some Matrix cast-offs that Katy Perry sang the demo tracks for, leading her on an alternative path that puts her in year 12 of fronting a fun but proudly minor league pop-metal band.⁵

This is all to say that there was to my mind only one point after Taylor Swift’s debut when she might not have become “Taylor Swift.” It was a precarious time in the music industry — the ceiling was dropping on music sales, streaming functionally didn’t exist yet, and most gauges of popularity were unstable. Nothing had to work, and most things didn’t. On the eve of Fearless, the same month as TARP and the bank bailouts, Scott Borchetta was talking about Taylor Swift in the LA Times like he was putting a risky bet on shorting the housing market and just saw the first signs of the bubble popping in his direction:

“We’re all keenly aware of what’s going on in the economy,” Borchetta said. “So the conversation really centers on the reality that the new album will do whatever the market will bear.

“But looking at the economy of scale, and at what a hugely successful record can do right now, it’s already hugely successful. The first single is screaming. We’ve had a half-million paid downloads for ‘Love Story,’ and ‘Fearless’ is just opening up. What that means by the time Nov. 11 rolls around, we have to kind of wait and see.”

And he was right to put it that way, because the Taylor Swift of Fearless is Michael Burry (Christian Bale’s character in The Big Short), the guy that made good on the collapse of recorded music as a commodity by being the last one standing.

But it didn’t have to happen that way — there didn’t have to be any winners at all. She could have gone down with the rest of them. She maybe should have. But she didn’t. And she has “Teardrops” to thank.

1. Cards on the table: I still think “Teardrops on My Guitar” is a maudlin drip of a song, my least favorite on the first album. I don’t remember ever hearing it on pop radio, but I did see it appear a lot on a web player of Radio Disney I occasionally kept tabs on without listening to the music—this would have been in early 2008—and I was mostly confused. …That one?

2. As “Teardrops” clawed its way up the charts over the course of that year, third single “Our Song,” which did better than “Teardrops” on country radio, had an easier time but left a weaker footprint on the pop charts: entered the top 100 in October and went up to #16 in January, 2008.

3. In the real world, Taylor Swift was #20 of 2008 on Radio Disney with “Teardrops on My Guitar.” In 2009 Taylor Swift was #1 on Radio Disney with “You Belong to Me” and #7 with “Love Story,” which means even her second-best performing Radio Disney single beat Selena Gomez. In 2009. On Radio Disney. That’s like the Washington Generals eating the Harlem Globetrotters’ lunch.

4. Some of them did just fine in very different lanes than country music, like Ke$ha, the last true MySpace weirdo crossover.

5. “Surely Skye Sweetnam was no Taylor Swift,” you say, as if her debut album wasn’t 100% songs she wrote herself, recorded in her music producer neighbor’s basement, and wound up good enough as-is to get her an opening slot on Britney’s Onyx tour in 2004. Skye Sweetnam is what happens without a “Teardrops” bridge to a perfect second album.