Taylor Swift's Incredible Decade: Marking the 10th Anniversary of Her Billboard Chart Debut

Taylor Swift performs on stage during the 1989 World Tour Live
Larry Busacca/LP5/Getty Images for TAS

Taylor Swift performs on stage during the 1989 World Tour Live at Ford Field on May 30, 2015 in Detroit, Michigan. 

When Swift made her Billboard chart debut 10 years ago, expectations were slim. But she transformed the pop machinery to her purposes, and kept her humanity in the process.

Imagine a world in which Taylor Swift is the very opposite of clickbait. It’s easy if you… well, no, it’s pretty much unfathomable even if you try, though those reading technically lived through that Paleolithic period -- that is to say, the proto-Swift years. It was exactly 10 years ago this week that era ended and a new one began as Swift made her first Billboard chart appearance: July 1, 2006, when debut single “Tim McGraw” inauspiciously bowed at No. 60 on Hot Country Songs. At that point, country radio, much less pop, couldn’t be bothered to care. The tabloids and rock press didn’t care. Vogue did not care. Truth be told, Tim McGraw probably didn’t even care. (Much. He is a polite guy.)

Her inability to get arrested by the media didn’t quite end overnight, as evidenced by the six months it took “Tim McGraw” to crack the country top 10. Those of us who were covering country as journalists at the time remember the calls from an independent publicist begging -- no, really, begging! -- us to give Swift a few inches of ink. But she really didn’t look like anything other than a promising novelty, since the history of young girls making it in country began and ended eons earlier with LeAnn Rimes.

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Here was a 16-year-old singing about real teen concerns in a genre where 30 was considered the demographic’s bottom end -- a girlish figure in the wake of the defiantly womanly Gretchen Wilson. Mildly intrigued by what I’d heard of the debut album, I went to see Swift perform at a low-key guitar pull in Nashville, sharing the stage with a few other acoustic guitar-strumming artists from her brand new label. I watched her take her turn singing about high school flirts and hurts and, with all the brilliant foresight and canny prescience I could muster, thought to myself: Good luck with that.

But Taylor Swift was already perfecting one of her greatest talents: the art of the end run. The curly-haired debutante that some of us were ready to alliteratively write off as Borchetta’s boondoggle ran long around the resistant radio programmers and press by galvanizing the audience she was rapidly collecting on social media (which, in 2006, of course, meant exclusively MySpace).

Those young fans called their local country radio stations demanding to hear “Tim McGraw” until handfuls of them finally realized it might be worth alienating a few older listeners to win the hearts of a few younger ones. That slow radio climb beget a first wave of adoring press. Press begat TV. And the rest is history, give or take a whiz-bang blizzard of MTV -- which cautiously began testing a remix of “Teardrops on My Guitar” toward the end of 2007 -- and Perez Hilton and arena multi-nighters and Grammys and Kanye and #squads and world domination.

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What it comes back to is the thing that it’s always been hardest for her detractors to believe: that Swift is the architect and auteur of her own career… both the art and the business of it. It didn’t matter that she wasn’t old enough to vote; she was old enough to drive pop culture, and do it her way. There were no Svengalis, or even stage moms. I remember talking with Andrea Swift early on, who struck me as not exactly Teri Shields when she assured me Taylor was self-driven: “Music was never my dream (for her). We were on a farm, and I had her sitting on a pony when she was 9 months old.

If my dream had gone well, she’d be in a horse show right now.” I talked with Liz Rose, everyone’s best guess at the time for the real brains behind the songwriter operation. But she seemed perfectly happy to declare that her function as Taylor’s co-writer was mainly to be her editor and sounding board. Big Machine had a lot going on, but the label was too nascent to be a Machiavellian machine. There was no managerial maestro pulling the strings.

Again, the early success only seemed overnight. “Tim McGraw” finally peaked at No. 6 on the Country Songs chart, but had little pop crossover. The second single, “Teardrops on My Guitar,” made it to No. 2 at country and No. 7 on Pop Songs. It wasn’t until “Our Song” that she had a country chart-topper, but that particular track had too much twang to cement the deal on the pop side. There was still a lot of uncertainty about whether her modicum of success at Top 40 was a fluke. She sold her first million albums without making too much of a dent on the pop consciousness. Some of us wondered aloud whether she could really break through without embracing someone else’s inner skank, if not her own, at least a little.

Toward the end of 2007 I sat down with Swift at an In-N-Out on Ventura Blvd. at the nexus where Hollywood meets the Valley. Besides the fact that Swift actually likes hamburgers, I think part of the idea was that my editors at Entertainment Weekly and I hoped that we’d prove she was crossing over to pop by portraying her as besieged by new fans at the busy burger joint. But during an hour of sitting there, only one young boy came up, meekly addressing her as “miss.” Yes, I wish I had some video to prove that even after she had a platinum record Taylor Swift sat in an In-N-Out for an hour, unmolested as she worked on a No. 2 with no onions and a chocolate shake (“It doesn’t count if you eat it out of town. That’s a rule,” she informed me).

She had as strong a sense of herself then as she does now, although there were a few moments that seem amusingly un-prophetic in retrospect. On the fact that she hadn’t had a boyfriend for years: “I’m not opposed to dating. I just haven’t found the right person that I’m gonna date. You want to hear my new career philosophy and my relationship philosophy? When I find someone who fascinates me as much as my career, I’m gonna go for it.” Lucky for everyone, probably, she managed to find some interesting boys after all. We also talked about her still bodyguard-free life, and I brought up the obviously troubled star of the moment. “You know, being compared to Britney… I haven’t been hounded for the last couple years of my life. I don’t know what that’s like, so I can’t ever speculate. I haven’t been completely mobbed everywhere I go. I imagine I would go crazy if every single thing I did, there were 30 photographers taking pictures of it.”

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Those were the least prophetic words she ever spoke. Because the 30 arrived, and then some, yet Taylor Swift became the legend of The Pop Star Who Did Not Go Crazy, Or Turn Into a Mean Girl On Us. (Yes, we know Katy Perry might beg to differ, but still.) You remember how those boys in Weird Science cooked up their vision of the perfect woman in a lab? Swift is practically the embodiment of what some Grammy board of directors would have created in a laboratory as the perfect pop star, if they could have. She’s a repeat Album of the Year winner who also happens to be zeroed in more than any other celebrity of note on philanthropic efforts. She’s seen as caring deeply about music education… whether that’s contributing millions to programs that foster the arts for kids, or just educating the public about why she thinks “freemium” sucks. And people in the industry and sick kids alike she has the ability to walk into a room and make everyone in it feel special, like no one this side of Dolly Parton.

Which, for all rights and purposes, ought to make her intensely boring. There’s a reason nearly every pop starlet plays the bad girl sooner or later, and it’s not necessarily because they’re all bad. Swift has maintained a credible image of public virtue and good-heartedness while making records with increasingly complicated emotions. The early trope was that her records were all about the guys who wronged her — and she certainly got some of her most scorching material out of that — but starting with “Back to December,” she proved perfectly capable of sharing her own culpability in song. In a tune like “Blank Space,” she could even play with the image of the good girl as future crazy ex-girlfriend who “can make the bad guys good for a weekend.”

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Her songs are meta, and they’re not. “Mean” could be the anthem for anyone who feels like an underdog, even if the “I… can’t… sing” line stepped out of universal character to hilariously refer to a very specific circumstance for her as a criticized celebrity. Fans scour the lyrics for offbeat details that confirm the sentiments came out of a real-life situation -- a mention of a scarf or pendant someone remembers seeing in a paparazzi photo, or of a month or location that registers in lore --  not so much for the purpose of confirming gossip as just authenticating that her stuff has the bracing ring of non-fiction.

It’s ageless, too… as in, non-age-specific, all those patronizing comments about “it’s fine for teenage girls” to the contrary. When I was first reporting on industry reaction to “Tim McGraw,” I was finding out from country radio programmers that their older listeners related to the material as something nostalgically remembered, if not recently experienced. Take away a few lines about cheer captains and bleachers in “You Belong With Me” and it’s the anthem for any adults who feel like they’re always playing the Eve Arden role in someone else’s romantic comedy.

The references to stitches and hospital rooms in “Out of the Woods” tell us this is autobiographical, and almost weirdly autobiographical -- but anyone who’s in a relationship they feel might still be in the forest just sings along with everything but that telling section. And the thought you might have had a “Last Kiss” and didn’t realize it at the time? It’s a rueful feeling experienced just as much by divorced fiftysomethings who are back on the dating scene -- trust us on this one-- as by listeners who are feeling 22 because, you know, they’re actually 22.

That individuality is why Swift stands out among a sea of singers who use the kind of hit producers profiled in the recent book The Song Machine: The Hit Factory. Swift uses Max Martin and a lot of the others now too, now, but to her own purposes -- as with Liz Rose in the earlier days, more as arrangers than credited ghostwriters (as the snippets of demos she tags on to her deluxe editions shows). She’s not just the ghost in the machine; she’s the spirit that commands the machine.

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So as much as some of us might want to bitch about how girl squads don’t really constitute feminism, she’s become a feminist icon over the gradual course of a decade because she’s earned it. Swift is powerful enough, certainly, to be a ballbuster, yet works well with others. Yes, it takes a village to make a pop star, but Swift has always been the chieftain of her own village -- creating the songs, imagining the tour designs, running the business -- at 16, as now at 26. A decade after that modest bow, in the year of Hillary, it’s Swift who has tens of millions of fans with that hashtag hovering in the back of their minds, just behind all those earworms: #I’mWithHer.