Taylor Swift sample

I wrote this for a 33 1/3 proposal on Taylor Swift’s Fearless. Figured I should put it somewhere.

The Confessional Teenpop Era and the Origin of Taylor Swift

It seemed inevitable that she would eventually take over the world. Born in a rural outpost of a major city to supportive parents who managed her celebrity dreams without micromanaging her vision, she was laser-focused on music from a young age: when most kids were playing sports or video games, she was studiously analyzing pop stars, scribbling lyrics on stray pieces of paper in her middle school cafeteria, teaching herself to play the guitar, performing whenever possible.

Barely a teenager, she lucked into a family connection with a major label and before she knew it was writing songs—or rewriting the songs from crumpled scraps still stained with remnants of her lunch—with a young producer who, contrary to the others who passed on this self-assured teen insisting on writing her own material, was more than happy to collaborate. Songs that she’d been humming to herself since childhood were taking shape in demos that wound up being good enough to fill her debut album.

She navigated the hottest new social media platform, MySpace, expertly, building a devoted fan base of children and teens just by being herself. She blogged constantly and encouraged fan campaigns to platforms like Disney’s radio station, Radio Disney, and stoked strong parasocial relationships in her fan forums. Her first single wasn’t a huge hit, but it got decent radio airplay in its niche, and before she knew it, she was opening for one of the biggest stars in her genre. She was already making grand plans for her big moment: the second album that would catapult her to stardom.

But that moment never arrived. The artist was Skye Sweetnam, and her second album flopped.

To understand why Taylor Swift succeeded and Skye Sweetnam didn’t, you need to understand the landscape from which Taylor Swift emerged. The question is why many artists with backgrounds like Taylor Swift’s failed, or only succeeded briefly, and why Taylor Swift did what none of them could manage: lay down roots with a young audience that grew with her over the next decade and beyond. Part of this story is about Swift herself—her canniness, adaptability, and talent—and the way that she translated her strengths into a concept album about teenage life that also appealed to children and their parents. But another part of the story in Taylor Swift’s early career is the expansion and contraction of millennial teenpop music as a field.

I use the term millennial teenpop music to refer to the explosion of youth music following the twin “invasions” of kid-oriented pop in the late 1990s: the “second British invasion” of the Spice Girls and the “Swedish invasion” of producer Max Martin and Cheiron Studios with Britney Spears and the Backstreet Boys. This music was created at the turn of the new millennium, but also closely tracks the Millennial generation (an “echo boom” encompassing people born between the mid-80s and mid-90s), similarly to how rock music evolved as baby boomers came of age in the 60s and 70s.

The evolution of teenpop’s sounds and artists was timed to the historically large Millennial generation reaching late childhood and puberty: its music “matured” along with its fanbase. Teenpop music took a turn toward earnest confessional songwriting with the rise of Avril Lavigne in 2002, and the production and songwriting norms changed: the sound was now rock-oriented in alternative and adult contemporary styles, with young singers expected to play their own instruments and participate in writing alongside professional songwriters. By the end of 2006, when Taylor Swift’s debut country album was released and the average Millennial (like Swift herself) was a teenager, most early teenpop stars had shifted into more risqué pop styles, while the confessional songwriting wave receded into a niche interest controlled almost exclusively by Disney and its record label Hollywood Records.

I call the five-year phase of millennial teenpop’s evolution between Avril Lavigne and Taylor Swift (2002-2006) the era of confessional teenpop. Although Taylor Swift started her career as an aspiring country music star, her aims were always to cultivate the kind of youth audience that had formed strong relationships to the stars of the confessional teenpop era: that is, children and teens who were fans of young women who wrote their own songs, played their own instruments, and detailed the exhilaration and heartbreak of life on the cusp of adult independence. If Taylor Swift had been born a few years earlier, she might have been lost in the shuffle of dozens of Avril Lavigne imitators; if her career had stalled by a year or two, she might have missed her opportunity altogether. Instead, the confessional teenpop era ebbed at the exact moment that Taylor Swift surged, enabling her to take center stage (along with the entirety of teenpop’s audience) on her mega-selling, career-launching breakthrough, Fearless.

Rock critics have long slighted confessional music as being open-hearted in a way that is distinctively phony or embarrassing. Lester Bangs infamously labeled James Taylor (whom Taylor Swift was named after) “marked for death” in a 1971 essay about rock ‘n’ roll’s grubby, libidinous strengths while extolling 60s garage-rockers The Troggs of “Wild Thing” fame: “The first mistake of Art,” he wrote, “is to assume that it’s serious.” Women rock artists are often shunted into the label of confessional music even when it is not their aim: they have historically been dismissed by (overwhelmingly male) rock critics for, as Rolling Stone co-founder Jann Wenner succinctly put it in an interview that got him kicked out of the Rock and Roll Hall of Fame foundation’s board of directors, not rising to the status of “philosophers of rock ‘n’ roll,” with the implication often being that their words are merely confessional. Long after the likes of Wenner perennially underrated Joni Mitchell’s rock ‘n’ roll artistry, women in rock were routinely accused of autobiography when they were engaging in imaginative fiction and careful poetry, their writerly and rock-philosophical ambitions reduced to journaling.

But there is also nothing wrong with wearing your heart on your sleeve, and almost everyone does it on occasion. Confessional music is a common songwriting mode with predictable features: its songs exhibit earnest realism, first-person storytelling, and a conversational affect to suggest a two-way autobiographical channel with a listener, free of the distancing artifice of pop’s machinations—it’s just you, the artist, and their life shared with you. That this isn’t strictly true is irrelevant: it feels true. Confessional music posits: “this happened to me, and it feels like it could happen to you, too.” These attributes apply to much more music than is usually labeled confessional—huge swathes of popular music, especially in genres concerned with conveying realness, like country music and hip-hop, do more or less the same thing from different social spheres than confessional folk-rock.

Widening the lens of confessional music beyond the legacy of folk-rock to other genres, while acknowledging its potential to buck perceived inauthenticity or stasis in a dominant musical style, helps to explain the specific shift from the rise of song factory teenpop music in the late 1990s to the dominance of the guitar-based rock music of confessional teenpop in the mid-aughts. It also helps to explain why country music, a genre with ingrained claims to plain autobiographical realism, eventually turned out to be the perfect vessel for Taylor Swift to extend confessional teenpop’s broadest reach.

Although artists like Britney Spears and the Backstreet Boys shared their lives and their teen (or at least teen-coded) feelings with their audiences, and certainly used formal features of confessional music, it was generally understood even among young audiences that they were singers performing material, and that they were not expected to have personally written or lived through the content of all of their songs. There was always implicit confessionality in teenpop music as a parasocial throughline for young fans, though. Britney Spears frequently conveyed confessional themes in songs about the travails of early stardom like “Overprotected” and “Lucky,” and her title lyric “I’m not a girl, not yet a woman” is perhaps the thesis statement of the teen confessional music to follow. But generally, one was not expected to believe that the primary way that Britney Spears created music was by lifting lines from her diary, getting out her guitar, and setting her inner life to music.

That understanding began to change during the peak of the teenpop zeitgeist in the early 2000s. Michelle Branch (with “Everywhere” in 2001) and Vanessa Carlton (with “A Thousand Miles” in early 2002) flaunted their songwriting prowess and musicianship in their public image, in Carlton’s case even wheeling a full piano through the suburbs in her music video. They were young women whose appeal lay in the idea that they wrote their own songs, played their own instruments, and sang about what were assumed to be experiences drawn from their real lives, or at least real feelings. Their music fit just as easily on adult contemporary radio formats alongside Celine Dion and Faith Hill as it did on the pop charts among increasingly adult pop offerings of former teen stars.

Avril Lavigne was the star who broke the scene wide open with her debut album, Let Go, and especially its lead single, “Complicated,” in 2002. Her influence on the confessional music to follow, including Taylor Swift’s, can’t be overstated: Taylor Swift even insisted to her Nashville demo producer Robert Ellis Orral in 2004 that she wanted one of her songs to sound “like Avril Lavigne, but country.” Lavigne started out as a country singer herself, performing country songs at festivals throughout Canada. After she got her record deal at sixteen, she pushed instead for production more in line with then-trendy adult contemporary, pop-punk, and nu-metal styles. She sang in clumsy teen vernacular (“chill out—whatcha yellin’ for?”) and incorporated high school imagery (“take off all your preppy clothes”).

But her sound on her breakout hit, whose followers would dominate pop radio for the next five years, was a jagged lilt—impossibly clean, syncopated acoustic guitars with a shuffling soft rock backbeat, like a coffee shop open mic night performance that lights up an arena. The sound combined post-grunge 90s alt-rock (especially via Alanis Morissette) with the muscular adult contemporary “mom Americana” style of Sheryl Crow. While Max Martin and the Swedish Cheiron Studios defined the sound of the first wave of millennial teenpop with a rigid hip-hop boom-bap beat offset by a light (and vaguely European) reggae bounce, the second confessional wave was dominated by producers more comfortable with traditional rock instrumentation to buoy angsty personal lyrics. This was music geared toward children and teens that nonetheless made a huge impact on what Billboard calls the Adult Top 40: “Complicated” eventually broke a record for most weeks at #1 on that chart previously held by Natalie Imbruglia’s “Torn.”

The Matrix production team, who co-wrote and produced “Complicated” with Lavigne, was a one-stop shop for angst-rock in the mid-aughts. Other producers who had worked extensively in rock and adult contemporary formats, like John Shanks, collaborated with a large stable of dependable songwriters-for-hire who were veterans of the 90s alt-rock scene but could also fire off pop hits for Gwen Stefani or Kylie Minogue: writers like Linda Perry, Kara DioGuardi, Shelly Peiken, and many others. These professional songwriters shared writing credits with young performers, who were routinely expected to bring their words and ideas to the table.

In the years from Avril Lavigne to Taylor Swift, there were countless young artists who tried to replicate Lavigne’s success with teen confessional rock music, none of whom succeeded to a fraction of the extent that Taylor Swift would at the end of the decade. Some of them were once household names. Ashlee Simpson, the little sister of a star of millennial teenpop’s first wave, Jessica Simpson, had a hit reality television show on MTV in 2004 that documented her work with a small group of professional songwriters (primarily John Shanks and Kara DioGuardi) to create diaristic pop hits: her debut album was called Autobiography and the follow-up was I Am Me. She looked to be a major pop figure until her public humiliation on Saturday Night Live in October 2004, when it was revealed she was lip syncing after she lost her voice in an acid reflux flare-up. Inaugural American Idol winner Kelly Clarkson drew from a successful grab-bag of contemporary pop styles on her debut album, Thankful, but contributed to Avril Lavigne’s confessional rock sea change on her hugely successful 2004 album, Breakaway, which was produced by a newly rock-oriented Max Martin and included a title track penned by Lavigne herself.

I cataloged the confessional teenpop wave contemporaneously in a monthly column for the proto-poptimist music website Stylus Magazine, where I wrote about major stars like Clarkson and Simpson, and, eventually, Taylor Swift on the precipice of her pop breakthrough. My favorite artists from this period were often strange, momentary success stories of young people with steely celebrity ambitions writing their own confessional pop music, like Canadian songwriter Fefe Dobson; charming Avril Lavigne followers like Katy Rose in the US and Amy Studt in the UK; and promising oddballs like future Academy Award winner Brie Larson, whose sole album on Tommy Mottolla’s Casablanca Records, Finally Out of P.E., I discussed with her via email for a column in 2007. She detailed firsthand how the music bizzers of the time were constantly on the hunt for young talent that could write and perform their own material, and bemoaned what she referred to as her “slip n slide to success,” a trajectory common to young artists of the era:

I fell in deep love with the guitar when I was about 11. I started getting “lessons” from various friends and such while I was on a TV show. We had a musical guest on the show, her manager took interest in me. All of a sudden, I had a manager all before I had even thought about putting a record out. I just loved music, man. I was just some scared little kid.

Well, my management wanted to make sure I could write music. So they set me up with some producers who really didn’t think I could write either. They gave me some dusty track called “Butterfly” of all things and told me to come back in a week. I did. I stood in front of them and sang my song and they were both floored. They turned to my mom and said, “Did you write that?” She laughed and said no. They took that song to a couple different labels. Tommy Mottola heard it and signed me sight unseen. “Butterfly” turned into “Invisible Girl” which was the first real song I had ever written. I guess the pop racket found me far before I found it.

Skye Sweetnam was a personal favorite from this period whose background fits the general template for teen stardom. Born and raised in Bolton, Canada, outside of Toronto, Sweetnam made the fateful decision to forgo snowboarding camp for Pop Star Camp at the age of 12. She recorded a few karaoke covers onto a CD that her mom would play over any loudspeaker she could commandeer in town. One day a regular from the local hair salon passed her demo on to a family member in the music business. She got a professional manager and was soon flying to Los Angeles to finalize a development deal with Capitol Records.

Back in Canada, Sweetnam worked with James Robertson, the 21-year-old son of a prominent local soundtrack composer, to write and record a dozen or so original songs in his home studio. The resulting album, Noise from the Basement, featured a regional hit single in Canada, “Billy S.” (for “Billy Shakespeare”), with the same lyrics she scrawled on notebook paper at lunch in middle school: “Teachers treat us all like clones, sit up straight, take off your headphones / I don’t blame them, they get paid / Money money, woo, lots of money money, woo!” The song was smarter than many gave it credit for: not just any eighth-grader sneers at English class while still referencing Twelfth Night in her pop-punk pastiche. The ensuing Canadian success got her an opening slot on Britney Spears’s Onyx Hotel tour in 2004.

But things got rocky as she started the second album. She wrote lots of new songs, almost none of which interested the label. After long delays, Sweetnam was saddled with sub-par cast-offs from the Matrix production team—an ironic turn for someone who toured with an anti-Matrix sticker on her guitar and once jokingly referred to herself in a song as “Avril Lite.” The sophomore album, Sound Soldier, was a commercial dud, and by 2008 Skye Sweetnam wriggled out of her contract with Capitol to focus instead on a garishly-costumed pop-metal band, Sumo Cyco, where she adopted the cyberpunk moniker “Sever.” That same year a different young woman born in the late 80s, whose musical coming of age was similar in broad strokes, was succeeding beyond any of Skye Sweetnam’s wildest dreams.

So why did Taylor Swift’s version of this story work? Part of the story is about who Taylor Swift was and where she came from, a similar story to many teen confessional hopefuls of the previous decade, but with a few important exceptions: chiefly, how she entered the field (via country music) and how she avoided the career development pitfalls of almost every other teen confessional star, a testament to an early clarity of the shape of her career, and to her willingness to push industry boundaries that eluded other artists and their often hapless stage parents. Another part of the story was just the luck of her timing: Taylor Swift made a wild bet on consolidating the entirety of the confessional teenpop audience—millions of young fans searching for their avatar and life raft on the choppy waters of adolescence—several years past the point at which there seemed to be any commercial viability in the project, and the bet paid off.

Taylor Swift’s backstory is summarized in a paragraph or two in almost every major feature written about her since 2007, of which there are now dozens. Swift grew up in Reading, Pennsylvania, sixty miles outside of Philadelphia—for color, you might add that she grew up on a Christmas tree farm her father owned. She was the daughter of affluent professionals: her mother was a marketing exec and her father a financial advisor for Merrill Lynch, who bankrolled Swift’s early career to the tune of several hundred thousand dollars for lessons, production, marketing, and travel. At 11, Swift recorded herself singing her favorite songs and started writing some of her own. At 12, she learned guitar on an ungainly twelve-string, finding the more common six-string much easier to play a few years later. By 13, the family had moved their aspiring singer-songwriter to Nashville, where she cut demos as part of a development deal with RCA, engineered by a one-time manager for Britney Spears. She broke the RCA contract and found new management at 14, frustrated that the label threatened to shelve her material until she was a few years older.

After RCA, she was introduced to Dreamworks executive Scott Borchetta, whose fledgling foray into country music distribution, the Big Machine record label, needed a flashy draw. At 15, Borchetta signed Swift and set her up with writer Liz Rose and producer Nathan Chapman, a young acolyte of John Shanks, who collaboratively wrote and produced the bulk of her first two albums with her. The debut self-titled album was designed in the pop-country mode of American Idol success stories like Carrie Underwood and Kellie Pickler. Songs from the album did well on country radio, and in 2007, its second single, the ballad “Teardrops on My Guitar,” crossed over to pop radio with an assist from a growing youth audience devotedly following Swift on MySpace, packing her live shows, and requesting the song on Radio Disney, where Swift would soon dominate. By 2007, she was opening for country star Brad Paisley and was already writing and producing her second album, which everyone hoped would capitalize on the fast-growing success of her country debut.

All around Swift, the music industry was in decline: in the years before the streaming era, album sales were plummeting while digital downloads could barely stanch the losses. This sense of the whole industry imploding was implicit in the conservative treatment of previous iterations of confessional teen stars in the mid-aughts, who rarely were allowed to follow their personal muses to strange places, even after a hit album. Having unshackled herself from a comparably conservative development deal with RCA, Taylor Swift found herself on a supportive label with the marketplace clout of a major but an indie’s sense of risk-taking and development of artist voice.

Meanwhile, memories of faded confessional stars had consigned the sound of confessional rock almost exclusively to Disney’s Hollywood Records label, which had numerous confessional teenpop artists on their roster saturating the company’s walled garden of content. Demand from Disney kids was encroaching the pop charts after Billboard started to account for digital downloads in 2005. This phenomenon was most visible when, in 2006, the fictional cast of Disney’s TV movie High School Musical beat several chart debut records previously held by the Beatles. Over the next few years, Taylor Swift would eclipse every Hollywood Records artist on Radio Disney—by 2009, she was their most-played act, a feat equivalent to beating the Harlem Globetrotters.

Taylor Swift found her audience obliquely from the country music charts, where claims to autobiography and authenticity were built into the fabric of the genre. Country radio had its own problems with the youth market. Ultimately, Taylor Swift’s audience assembled itself, just like Disney’s young downloaders stormed the Billboard charts armed with parental allowances on their iTunes accounts. As Country Music Television executive Brian Philips put it in October of 2008, “It’s as if Taylor has kind of willed herself into being.” By the time Fearless was released in November 2008, there was no one standing in Taylor Swift’s way: she captured the teen confessional audience, even from the one company whose music business model depended on her not succeeding. Fearless was not just an immediate success; it was a coronation.

Taylor Swift was the perfect representative for family-friendly music that appealed specifically to the moods and dreams and desires of young people. She was a nice girl from Pennsylvania who wrote her own songs and played her own guitar and sang about her friends from high school. She was acceptable to parents—she was an antidote to the often raunchy offerings of “grown up” teen stars and didn’t use a curse word in her music until 2017—while using the teen confessional mode to speak directly to their children, sharing secret knowledge of the adolescent world that child fans were entering and teen fans were navigating. She was the authoritative older sister of your best friend introducing you to a world of emotional turmoil, gesturing towards the ecstasies and anxieties of the lives of adults, all while your parents hovered in the next room unawares, never suspecting as they listened along that your life was changing. By the time Fearless came out, there was no one else around to guide you: it was just you and Taylor Swift, facing the future together.