Taylor Swift’s Career Timeline (Part 1): Debut to Reputation
Taylor Swift 101 Series, Episode 2
Podcast Episode: October 2, 2025
Episode Description
There was a time when Taylor Swift got rejected from every record label she approached. Today, there would be a billion-dollar bidding war to get the chance to work with her. So how did she get here?
This is part one of the complete timeline of Taylor Swift’s career, from her beginnings as a small town girl in Pennsylvania to her rise to the top of the charts. We’ll uncover how she crafted one of the most remarkable careers in modern music, and how she used storytelling to get there.
We’ll discuss her fresh-faced country debut with her self-titled album, the bold and glittering fairytale of Fearless, her first concept album Speak Now, the heartbreaking tracks of Red, the pop-minded 1989, and her post-cancellation comeback (and most iconic album), reputation.
Through her eras we’ll uncover how she built the Swiftie fandom brick by brick, what made her unique in the pop music landscape, and how her songwriting has changed from album to album.
This is the story of Taylor Swift, from one carefully crafted era to the next.
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Episode Transcript
Timeline-Part-1
[00:00:00] Taylor Swift and her mother Andrea are walking up and down Music Row in Nashville. In their hands, they’re holding homemade copies of burn CDs on which Taylor sings karaoke to songs from Leanne Rimes, the Chicks, Dolly Parton and Olivia Newton-John. 11-year-old Taylor Optimistically passes out these CDs crossing her fingers that one of these record execs will hear something they like and give her a chance.
But it wasn’t to be
She either never heard from them or got rejected outright from every single label she approached.
Today there would be a bidding war, the likes of which the world has never seen for any label to be able to work with Taylor Swift. So how did we get here? Taylor made one choice very early in her career that changed the course of her entire life. Without this one single thing, which I’m gonna talk about today in this video, she would not be one of the most powerful and influential artists in the entire world.
Welcome to Swiftly Sung Stories. I’m Jen, and I am so glad that you are here to geek out about Taylor Swift with me Today, I wanna cover a really hefty topic, [00:01:00] a complete timeline of Taylor Swift’s career, the most important events and choices in her artistry that made her the cultural phenomenon of the century.
But before we dive in, it’s important to note that I said Taylor Swift’s career, not Taylor Swift’s life. I am a writer and I’m a former English teacher, and that is the lens through which I dissect Taylor’s work. I don’t dive into the drama or her personal life. I just look at the art and what the art does.
This is the timeline of Taylor Swift’s career. Not just what she’s done, but how she’s done it. I hope this will give you a clearer picture of just how Taylor built one of the most remarkable careers and catalogs in modern music, one carefully crafted era at a time. This is the story of Taylor Swift. Let’s get started.
[00:02:00] It is the year 2000 country singer Faith Hill, married to Tim McGraw, topped the charts that year with her song Breathe. And we can imagine 11-year-old Taylor Swift just watching that music video over and over, dreaming about her future writing in her diary and practicing her little heart out. It was, in fact, after watching a documentary about Faith Hill on VH1, taylor decides that this is it. This is what she wants to do for the rest of her life. She wants to be a country artist. Taylor’s parents are of course, super supportive, and it’s later that year that her mom, Andrea Swift takes her from their home in Pennsylvania to Nashville with these homemade cover song demo tapes.
You know what happens next.
Nashville Recording studios weren’t looking for karaoke. They weren’t looking for performers, they were looking for songwriters. Nashville is after all the songwriting capital of the world, but instead of being sad [00:03:00] and disappointed, Taylor pivots, which is a move we will see again and again for the rest of her career.
She decides that if they’re looking for songwriters, she’ll become a songwriter. She goes home, picks up a pen, learns the guitar, and at just 11 years old, she starts writing songs. She’s never stopped
at this point. She’s not even a teenager yet. She’s just a kid with a spiral notebook full of lyrics and a very clear vision. But it would be a long time before she was smooth sailing towards success. Her parents are really the guides of her career at this point, and they get her a talent manager, which helps her score some modeling deals for visibility.
She does perform at some small local gigs and festivals, and after working and going to school for years, her family makes a decision. If she really wants to be a country songwriter, they have to move to Nashville. It’s after this move that she gets her big break, she gets to perform some original songs at an RCA Records showcase.
It’s from the showcase that she gets her very first deal an artist development contract at [00:04:00] RCA in Nashville. An artist development deal is really a pre-recording contract where a label gives you the tools you need to grow in exchange for future rights, and a hefty cut of the earnings for whatever records you then put out is at RCA that Taylor meets Liz Rose, who had become a longtime collaborator and is a co-writer on her first two albums.
Rose said that working with Taylor was some of the easiest I’ve ever done. Basically, I was just her editor. She’d write about what happened at school that day. She had such a clear vision of what she was trying to say, and she’d come in with the most incredible hooks.
But even though Taylor is growing as a songwriter and she’s found a great writing partner, she’s not really growing under RCA, she was scared that this development deal would push her into a corner and said, I genuinely felt that I was running out of time. I wanted to capture these years of my life on an album while they still represented what I was going through.
I love this quote so much because it tells us so much about her mindset. She’s concerned about authenticity. She doesn’t wanna be in her twenties [00:05:00] putting out songs about high school. She wants momentum, and she wants her music to really speak to her audience. From the heart. She’s feeling the clock ticking already and knows that the lifespan of an artist can be really short.
So in 2004, she leaves RCA and she moves to Sony. She was the youngest artist ever signed by them. And in 2005, she is performing at the iconic Bluebird Cafe in Nashville. Which you’ll recognize if you’ve ever seen the the soapy drama in Nashville. But it’s here that the trajectory of her life really changes, again, both for better and for worse.
Scott Borchetta is in attendance at this performance, and he’s thinking about leaving his executive position at Dreamworks and starting his very own record label. We don’t really know the details of what went down, but she ends up signing with Big Machine Scott Borchetta’s brand new label. In 2005, Taylor’s father, Scott Swift, even purchased a 3% stake in the company.
So they are all [00:06:00] in on this new label, even though she’s one of the very first artists and only artists to sign with them.
For the next year, Taylor is just writing, writing, writing. She goes to school, she goes to write with her collaborators after school, she goes home, she does her homework, she goes to bed, and she does it all over again the next day.
She’s already an incredibly hard worker and she’s dreaming nonstop about her first album. One day when she’s sitting in math class, she comes up with a chorus to Tim McGraw. She plays the song for Borchetta and he immediately deems it the first single for Taylor’s new upcoming album. We can say a lot of things about Borchetta in hindsight, but he did get this one thing spot on.
Having a first single from brand new artist that name checks a very well known artist, is absolutely brilliant.
It immediately gets Tim McGraw’s fan base on board as well as Faith Hill’s fan base. And then all of these people will wonder, who is this young girl? singing about Tim McGraw, she’s using the cachet of another artist to draw attention to herself, so we can see already [00:07:00] her and her team are playing chess.
When everyone else is playing checkers,
they work out the rest of the album. And while putting it together, Taylor decides to do something that will change the trajectory of her life again and the lives of all of her fans. In doing the artwork and liner notes for Taylor Swift, she decides to leave secret messages spelled out in capital letters for a picture to burn it’s date.
Nice boys for teardrops on my guitar, it’s, he will never know. For should have said no. It’s Sam. Sam. Sam, Sam, Sam. Name checking the person who the song is supposedly about. This seems like a tiny detail and just a fun little thing to include, but it does so much more. These little easter eggs do a few very important things that will impact the rest of Taylor’s career.
Number one, it makes her music interactive. She’s not just putting out an album that lives on its own. She’s creating a game with her fans. Number two, it creates mystique. Suddenly, we’re not just curious about the music, but we’re curious about the artist herself. What’s her life like? Who’s [00:08:00] the song really about?
What happened to make her write it? And number three, it grounds her in reality, as I covered in my last episode, why Taylor Swift Matters. The popular songs of the early aughts were catchy, but they weren’t really emotionally relatable. But here comes this small town girl singing about real emotions and real things that happened to her.
And we know it’s real because she’s telling us it’s real in these secret messages. It takes her songs out of the ether and into our real everyday world. The secret messages are the one thing that would really change the future for Taylor. It creates a sense of intrigue and layered meaning that few other performers have ever been able to accomplish, and she did it from the very beginning.
This is, in my opinion, the essential move that not only created the Swiftie fandom, but helped make Taylor’s career really skyrocket. She established a connection with her audience from the very beginning, and that audience would be incredibly loyal. Her self-titled debut album released in October, 2006 [00:09:00] and was released a few more times after that.
Taylor spends much of 2006 in 2007 promoting her new album, doing radio and TV appearances, and she even scores a spot as the opening act on Rascal Flat’s tour. After that success, she gets to open for George Strait, Brad Paisley, even Tim McGraw and Faith Hill. She’s gaining popularity and name recognition.
And it’s here very early in her career that she first crosses over into mainstream pop music, teardrops on my guitar, starts getting pop radio play, and suddenly she’s not boxed into the country genre anymore. She’s making music with widespread appeal. But why does it have such widespread appeal? I believe it’s because Taylor was storytelling when the rest of the music industry was just narrating. In this era, both country and pop genres were a little bleak. We had sexy performers. We had one hit wonders and occasional singer songwriter hits, but for the most part, it was songs like Daniel Powders, bad Day, Nelly Furtado’s Promiscuous, and James Blunt’s [00:10:00] You’re Beautiful on Repeat. The country charts were full of the classic. My dog died, my truck died. My wife left type of songs, which is storytelling, but it’s not exactly relatable for fans outside of Middle America. The industry as a whole was really lacking a voice for young people. The early aughts were kind of a music desert, and I say this as someone who lived through this bleak period in my mid twenties.
Personally, I leaned heavily into alternative and indie artists During this period. I didn’t actually listen to the radio that much because it just didn’t resonate with my life. So when Taylor comes on the scene singing about heartbreak of losing your first love, these everyday experiences of being a teenager about pining for your crush, you doesn’t notice you.
She’s bringing something totally different to the table. She’s singing songs about universal emotions at a time when mainstream music just wasn’t. The songs on debut really tap into the experience of being a young person and especially a young woman, but it’s also about the way she’s doing it by telling stories.[00:11:00]
She’s not saying I like him, but he doesn’t like me back. She’s saying “he’s the song in the car I keep singing, don’t know why I do.” She’s not saying, I hope you remember me. She’s saying, “when you think Tim McGraw, I hope you think my favorite song.” We immediately feel what she’s singing about because she’s telling us the complete story, how it started, how it continued, how it ended.
Storytelling, is how we make sense of our lives. We try to connect events to make meaning. Telling a story is way more effective than just saying, I’m sad. We need to hear what happened, what it felt like, what the outcome was, and what you learned. We need all that information to be able to connect emotionally to others.
So here’s this new young artist who writes her own songs about her own life, and she’s telling us these stories in a way that allow us to connect and make these stories our own. Taylor said to Billboard in 2008, “The problem with the music business today in trying to capture today’s youth is they’re trying to hard the, there are record [00:12:00] labels that are admitting to the fact that they’re trying to copy the model that has worked for Taylor Swift in big machine records.
And the thing is, we just didn’t know any better. I was 16 years old and wrote all these songs about being in high school and sophomore relationships, not thinking that people would relate to it, hoping they would, but there was really no business model to make it work for the younger demographic. If we can relate to lyrics, then we’re going to buy the music.
And I don’t think that’s a hard formula to figure out.
People my age are really, really honest about what they like and what they don’t, and they know it when they hear it, and they know if they can relate to the lyrics.” This is the heart of why Taylor was immediately successful. We didn’t really have any other popular artists that were telling stories that were really about ourselves.
In 2008, Taylor won a bunch of awards for her self-titled debut album, but there was one particular award that would really define the next era of her life.
She won Nashville Songwriter Association, songwriter of the Year. She was the [00:13:00] youngest person ever to do so. This really cements her status as a serious songwriter.
she’s not just a singer or a performer. This is her trajectory, and this is what will fuel the rest of her career so successfully.
While she’s on the road promoting, debut, and opening for other big names, she’s also writing fearless. When Fearless is finished, it has 13 songs on it. Her lucky number and eight of those, she’s written entirely on her own.
It’s released in November, 2008, two years after her self-titled debut, and this is what ends up setting her two year album cycle that she’ll continue for the rest of her career. She releases an album, then immediately starts working on the next album, all through touring and promotions. She’s just always writing wherever she is.
Later on in the Fearless Taylor’s version prologue, we got a bit more context about this album. She says, fearless was an album full of magic and curiosity, the bliss and devastation of youth. It was a diary of the adventures and explorations of a teenage girl who was learning tiny lessons [00:14:00] with every new crack in the facade of the fairy tale ending, she’d been shown in the movies.
Fearless is the first time that we’ll hear a common metaphor in Taylor’s lyrics, life and love as a fairytale, and her career as her kingdom. Love story is the first single, and this song skyrockets to the top of the charts, and it’s the first country song ever to top the billboard pop charts. The rest of the album is an absolute smash, and it’s still the most awarded country album of all time.
It crosses over seamlessly between country and pop, and it’s really indicative of where Taylor’s career is heading. Fearless is full of starry-eyed love songs, heartbreak tracks coming of age songs, and angry breakup anthems all laced together with this fairytale imagery and metaphors. The jump between debut and fearless was a big one, and it really shows us how Taylor’s songwriting has expanded in the last two years of working, touring, writing, and recording. The lead single love story is a great example of her narrative songwriting and throws us into this world of an imagined happily ever [00:15:00] after, where Juliet will capture her Romeo.
It’s also a good example of what will become one of her signatures, which is this cinematic style, zooming in and out of moments and tying it all together to tell a cohesive story. You Belong With Me is a peppy look at unrequited love and taps into the world of an angsty teen so tactfully. These two tracks almost immediately get mainstream radio play and further cements this trajectory that she’s on country music as a springboard into pop. The Fearless album catapults Taylor into the world of Superstar.
She’s on Ellen, good Morning America. And Letterman. She performs at the CMAs and the AMAs. And while promoting Fearless Taylor is often asked about who these songs are about, what inspired them, and she admits very early on in her career that she’s inspired by everything. She doesn’t have to write from personal experience to convey her emotions.
she said to Billboard, you know, songwriting is all about being able to paint a story and tell a story, and sometimes that’s telling a story to [00:16:00] yourself. She said in another interview, “I’ve gone through breakups and the core emotions behind them, but it doesn’t take much to get that sort of emotion out in a song,
luckily for me.” What she’s saying in other words is that not all of these songs are about her real life. But since she gave us those secret messages in her first album and her life was about to get very, very public, very quickly, fans are reading between the lines. She’s built this curiosity about our personal life and it’ll be a very complicated line she’ll have to walk for the rest of her career. It’s now 2009 and Taylor has embarked on her first ever headlining tour. The Fearless Tour. Fearless is sweeping all the award shows. She’s on top of the world Fearless Wins album of the year at the CMAs and the ACMs, and it’s nominated for a ton of Grammy awards.
But unfortunately Taylor wouldn’t really get to bask in her success . Come award show season, a whole lot of conflict and criticism was coming her way.
In [00:17:00] 2009, you Belong with me was nominated for MTV’s Best Female video of the year. It won, and you all know what happened next. A young, optimistic and overwhelmed 19-year-old Taylor takes the stage and begins her acceptance speech. Then Kanye West jumps up on stage takes the mic from Taylor and interrupts her speech with his infamous Taylor. I’m gonna let you finish. He stole the stage and the spotlight insisting that Beyonce should have won the award. I’m not gonna play you the clip because you’ve probably already seen it, and I certainly wouldn’t want my most traumatic moments replayed over and over again on the internet.
But what happens is this, the crowd immediately starts booing. Taylor is standing up there confused and embarrassed, and she thinks that the crowd is booing her. She assumes everyone agrees that Beyonce should have won. It was a traumatic moment that would forever change the direction of her career, and this particular nemesis would try to come her again and again.[00:18:00]
But though this may have been her first public embarrassment, there was more to come in her fearless era. In 2010, Taylor performed three songs at the 52nd annual Grammy Awards. Today was a fairytale, which she played solo, followed by Rhiannon, and you belong with me with Stevie Nicks
which must have been an absolute dream for her.
But these were not Taylor’s best performances. And when Fearless Swept the Night winning album of the Year and Country Album and Whitehorse won Best Country song, the critics were very loud and very vocal.
They criticized her voice, her looks, her talent, her stage presence, but one of these things hurt more than the rest. They doubted that she really wrote these songs on her own. She’s devastated because songwriting really is the heart of where her talent lies. They’re questioning and doubting the very basis of her talent but she’ll go on to make a move that will prove [00:19:00] everyone wrong, and she does it in the form of her next album.
It is now later in 2010, the same year that Fearless swept the Grammy Awards, she’s wrapping up her first headlining tour, the Fearless Tour. But we know that our girl never stops working. In October, Taylor releases her third studio album, Speak Now. two things are different about this album. Number one, it’s a concept album about things left unsaid.
That means all the tracks surround this theme, and it doesn’t really mean that what she’s writing about is her current life. She’ll use this tactic again later on in midnights. And two, it’s entirely self written. No co-writers just Taylor Swift. We didn’t know it at the time, but we later got to learn a lot about what inspired Speak Now to be entirely self written. In the Speak Now Taylor’s Version prologue, we got to hear what was really going on behind the scenes. She says, “In my darker moments, I was tormented by the doubt that swirled loudly around my ascent and my merits as an [00:20:00] artist. I was trying to create a follow up to the most awarded country album in history, while staring directly into the face of intense criticism.
I had been widely and publicly slammed for my singing voice and was first encountering the infuriating question that is unfortunately still lobbed at me to this day. Does she really write her own songs? Spoiler alert. I really, really do.”
Speak now, in other words, is her first real clap back album. The songs within it might be about specific conflicts, but the album as a whole and putting it out with only her name in the liner notes is the real message. We can see that while writing it, in the back of her mind are all these critics who say she can’t sing, she can’t perform, so she makes another move in an effort to never hear that stuff again.
“I wanted to get better, to challenge myself and to build on my skills as a writer and artist and a performer. I didn’t wanna just be handed respect and acceptance in my field. I wanted to earn it to try and confront these [00:21:00] demons. I underwent extensive vocal training and made a decision that would completely define the album.
I decided I would write it entirely on my own. I figured they couldn’t give all the credit to my co-writers if there weren’t any, but that posed a new challenge. It had to be really, really good. If it wasn’t, I would just be proving my critics right.”
So two important things. Number one, she trains up. She gets a vocal coach. She really works on her singing voice and her performances. And then number two, she writes the entire damn album by herself to say, look what I can do. This is me.
Needless to say, speak now was very, very good. It’s also incredibly emotionally honest. If fearless was the fairytale ending, being rescued by a prince, Speak Now is where the princess climbs down the tower by herself, hops on a horse, and saves herself. Though Speak Now didn’t sweep the awards circuit like Fearless did, it is a more complex album and really shows Taylor’s songwriting [00:22:00] growth. Her metaphors are frequent and sharp. Her imagery is growing more descriptive, and the themes are getting a lot more mature and less black and white. Though she’s still got that youthful optimism, she’s also reflecting on the big lessons she’s learned.
Dear John, for example, is an open letter that looks back on her naivete and wonders what kind of person would take advantage of a young girl. And yes, it’s probably about creepyJohn Mayer. Never grow up, reflects on how far she’s come, how scary adulthood is, and questions whether she’ll ever feel the safety of childhood again.
The story of us uses an extended metaphor of a relationship as a storybook, and Long Live uses the fairy tale imagery and metaphors of fearless to commemorate her hard work and thank the people who helped get her there. In Mean, she directly bites back at her critics who tried to tear her down and prophesized her future success. In Innocent, she seemingly forgives Kanye for his mic grab.
But one of the most important lessons we learn as we grow [00:23:00] up is that nothing is black and white. And with speak now we got to watch Taylor learn this lesson in real time. You can love someone deeply and also hurt them badly. You can be hurt deeply, and you can still forgive. You can grow up and move on, but never forget where you came from.
You can regret not saying something and realize it’s not too late. She’s learning these lessons as she grows, but one lesson she would learn in a very unfortunate way
While on her speak now tour, Taylor does a meet and greet in Denver Prior to her show. At this event, a radio DJ poses with her, reaches up her skirt and gropes her. Taylor immediately reports it, the DJ, who I won’t name, because he doesn’t deserve any recognition, gets ejected from the stadium and fired from his job. This incident must have felt incredibly violating. And though to some it feels like a small thing, no one deserves to be touched without their permission, especially in such an overtly sexual way, and especially while you’re at work. We wouldn’t [00:24:00] hear about this incident until a few years later, but it must have been formative.
It must have felt incredibly violating and icky, and it likely made her question what her fame means. Are people entitled to a piece of her because she’s famous? What does she owe them? Does she owe them anything? How much of herself can she give before she breaks? And while she’s growing within this treacherous world of female superstardom, she’s also moving further and further away from her country roots.
And by her next album, they’d be all but completely severed.
Taylor began writing Red while on her Speak Now tour. With Speak Now, she had proven that she could do it all on her own, but she was already conscious that the clock was ticking. There was a time limit and she wanted to do more. She’s no longer a newbie. She’s eager to spread her wings and she wants to learn.
She said, I’ve always been aware of what my detractors say because I use it as a springboard for what to do next. With red, I had a different thing. I wanted to prove a thirst for [00:25:00] learning. She’s straddling this border with her original country fans, still thirsty for more, but also more solidly crossing into the pop world.
I was standing on a state line, she said, and I had a foot on either side of the borderline. She begins recording in Nashville with her usual producers for the first year of this album, but then she heads to LA to work with Max Martin and Shellback for the second year. They would soon become longtime collaborators.
After Red, she said she looked at this new world as going back to school, the school of pop music. The result is a conglomeration of these two worlds. ” It was sort of a metaphor for how messy a real breakup is, “she said, and this is my only true breakup album. I love Jackson Pollock, and I see this album as my splatter paint album, just using all the colors and throwing it at the wall and see what sticks”.
At the heart of it, Red is a breakup album, but it’s not just, we broke up and I’m sad. Instead, it takes us on an entire [00:26:00] emotional rollercoaster from beginning to end. She later told us in the Red Taylor’s version, prologue, “musically and lyrically red resembled a heartbroken person. It was all over the place, a fractured mosaic of feelings that somehow all fit together in the end, happy, free, confused, lonely, devastated, euphoric, wild, and tortured by memories past like trying on pieces of a new life. I went into the studio and experimented with different sounds and different collaborators. I’m not sure if it was pouring my thoughts into this album, hearing thousands of your voices sing the lyrics back to me in passionate solidarity, or if it was simply time, but something healed along the way.”
This incredible album begins with state of grace, which gives us sort of the thesis for the album. “Love is a ruthless game unless you play it good and right,” but this also foreshadows the darker themes to come. The game of love will not be played good and right. It will be played messily and intensely, [00:27:00] and in the end, no one wins.
Next is the title Track Red, where Taylor uses color metaphors and symbolism to portray the intense emotions of love.
This begins a theme in Taylor songwriting that we’ll see over and over again the colors of love and emotions used as extended metaphors. And this symbolism will pop up again and again on most of her albums to come. Then we move on to track three treacherous, where she compares this love to walking on a cliff or a tightrope.
She knows it might end badly, but becomes addicted to the adrenaline track four, I knew you were trouble, is the track that says the quiet part out loud. It’s full of regret and self-loathing and I should have known better. It’s also the first true pop song on the album, and in my opinion, Taylor’s first 100% true pop song overall.
But if the album’s thesis is “love is a ruthless game,” the album’s expository essay is All Too Well. It falls at Track five, which are [00:28:00] known to be the most vulnerable and raw tracks on Taylor’s album, and it definitely fits the bill. But the song is where for me, Taylor’s songwriting changes forever.
Long before the 10 minute version or the short film existed, this song already feels cinematic. We see what kind of a storyteller she’ll become in this song, and we’ll dive into all too well the 10 minute version in future videos. But for now, The important thing to remember is it’s a turning point in her writing. All Too Well is a masterpiece of narrative storytelling. We get to hear the complete rise and fall of this doomed romance peppered with these cinematic flashbacks to when they were happy and when she was sad. The song is a novel’s worth of storytelling told in only a few verses and choruses.
Red was released in October of 2012. And in the original prologue we see another shift that Foreshadows Taylor’s future. She includes a literary reference.
There’s an old poem by Neruda that I’ve always been captivated by, and one of the lines in it [00:29:00] has struck with me ever since. The first time I read it, it says, love is so short. Forgetting is so long. That poem is “Tonight I Can Write” in parentheses, “the saddest lines”, and it’s an absolutely soul crushing work by Pablo Neruda about losing a lover and letting that grief fuel your writing.
Taylor really took this poem to heart for creating red, and including the quote does something important. It lets us know that she’s a serious writer. While before she had mentioned Shakespeare and Robert Frost in passing, the Neruda quote says, I’m not just a country singer or a pop performer. I am a writer.
But as incredible as this album is, and as serious a songwriter as Taylor is, the press surrounding Taylor in 2012 is not about the music. She’s become a tabloid fixture and subjected to an incredible amount of scrutiny about her personal life, her body, her boyfriends, and her choices.
She’s opened this door to her personal life by writing about it [00:30:00] and by writing about the people she’s dated. But while many of us understand that she can do that and yet is still entitled to a private life, the press and lots of the public on social media don’t understand the nuance. This is a line she’ll have to walk for the rest of her career.
But in 2012, this is the first time it’s really getting unbearable. Taylor is in a word being slut-shamed. She’s painted as a serial monogamist and a crazy, bitter ex-girlfriend who only writes scathing songs about her former flames. This new round of criticism would shift everything, and in an attempt to quiet the never ending chatter and speculation, she’d soon shapeshift into an entirely new artist.
In 2013 and 2014, Taylor is on her red tour breaking all the records and working nonstop. But all the while she’s having to deal with these constant headlines from debut to speak. Now she’s America’s sweetheart, the good country girl, with a clean [00:31:00] cut image and long, curly blonde hair. But within our patriarchal world, dating boys isn’t compatible with being a good girl.
Her reputation and her image are at stake. So what does she do? She becomes someone else. In 2014 Taylor moves to New York City and takes inspiration from the big apple for her next shift. At the time we saw this visual shift : gone were the long blonde locks and at its place was this short bob, RayBan shades bright red lip, but it wouldn’t be until 1989 Taylor’s version that we were clued into what was really going on behind this transformation.
In the 1989 TV prologue, she says, “when I was 24, I decided to completely reinvent myself.
How does person reinvent herself? You ask in any way I could think of musically, geographically, aesthetically, behaviorally, motivationally, and I did so joyfully. The curiosity I had felt the first murmurs of while making red [00:32:00] amplified into a pulsing heartbeat of restlessness in my ears. The risks I took when I toyed with pop sounds and sensibilities on red, I wanted to push it further.
The sense of freedom I felt when traveling to big bustling cities. I wanted to live in one. The voices that had become to shame me in new ways for dating like a normal young woman. I wanted to silence them.”
She takes inspiration from her birth year for which the album is named, but also takes inspiration from that entire decade of music. She returns to the studio with Max Martin and Shellback, her pop minded collaborators from Red and someone new joins them : up and coming producer Jack Antonoff. If you’ve heard his band Bleachers, you know that Jack also takes a lot of inspiration from eighties pop.
And what emerges from Electric Lady Studios in New York is a 100% pop album backed with electronic bass beats, synthesizers, multi-track backing vocals, and those signature eighties keyboards. [00:33:00] Her sound changed dramatically and her look changed dramatically, but the contents of her songwriting really changed too.
if red is the depressive breakup phase where you bundle yourself under the covers and cry into a pint of Ben and Jerry’s every night? 1989 is the revenge phase where you cut your own bangs and go out and get drunk every night with your girlfriends. Keep in mind, the media was already portraying Taylor as a slutty party girl anyway, so in 1989, instead of trying to distance herself from that narrative, she just leans in.
She says, in the years preceding this, I had become the target of slut shaming the intensity and relentlessness of which would be criticized and called out if it happened today. The jokes about my amount of boyfriends, the trivialization of my songwriting, is if it were a predatory act of a boy crazy psychopath.
The media co-signing of this narrative, I had to make it stop because it was really starting to hurt. It became clear to me that there was no such thing as casual dating, [00:34:00] or even having a male friend who you platonically hung out with. If I was seen with him, it was assumed I was sleeping with him. And so I swore off hanging out with guys, dating, flirting, or anything that could be weaponized against me by a culture that claimed to believe in liberating women, but consistently treated me with the harsh moral codes of the Victorian era.
Being a consummate optimist, I assumed that I could fix this if I simply changed my behavior. I swore off dating and decided to focus only on myself, my music, my growth, and my female friendships. If I only hung out with female friends, people couldn’t sensationalize or sexualize that, right? I would learn later on that people could, and people would, and still do.
So this is her plan. Live a life that can’t be criticized and write an album about it. Did it work to silence the slut-shaming? No. But is it one of her best albums? Yes.
1989 Opens with Welcome [00:35:00] to New York, which firmly sets the tone that this is not the old Taylor: she can’t come to the phone right now. ” It’s a new soundtrack,” she says in that song, “I can dance to this beat.” She’s living an entirely new life as an entirely new person. She’s no longer the small town girl living in a lonely world.
She’s a big city girl.
Then in the second track blank space, she leans into the slut shaming narrative with satire. She couldn’t beat the media at their own games, so she joins in with this tongue in cheek track that basically says, I know exactly what you’re saying about me, so I will exaggerate the story and I’ll make fun of you for making fun of me.
The music video is just the icing on the cake where we get to see her act out this Mad woman satire. She also bites back in songs like Shake It Off, bad Blood and New Romantics. This is a new Sassy Taylor whom we saw glimpses of in songs like Mean, and we are never getting back together and would become even more amplified in her next album.[00:36:00]
But the other half of this album, despite her assertion that this is about moving to New York and having fun with friends still contains a lot of heartbreak songs similar to Red. This time it feels like she can never quite get what she wants in love with songs like Out of the Woods. I wish you would Wonderland.
all you had to do is stay. Is her track five for this? By the way, and this is the only time I disagree with placement of a Track Five, for me, the most powerful and vulnerable song on 1989 is Clean, which clocks in at tracks 13. It’s still an important number, but I think clean is so much more powerful than all you had to do is stay.
But 1989 is really where Taylor’s superstar power goes to a new level. She wanted to reinvent herself and she really accomplishes it. It’s a massive hit with a whopping seven singles. It went platinum and sold 14 million copies. And this was around the time when streaming was taking over physical record sales.
We no longer had to buy physical albums to listen to [00:37:00] them. Apple Music was taking over since we all now had iPhones, and they offered subscribers a free three month trial period to tempt in new listeners, but there was one major hangup. They didn’t pay artists for music streamed during those free trial periods.
What happens next is the first time we really see Taylor step into her power as a business woman, she and her team withhold 1989 from streaming. Remember, this was the second bestselling album of 2014-2015, so it was a major draw for Apple Music and its customers. She wrote an open letter to the platform explaining exactly why this was bad for artists, but especially new artists and ones that were just trying to make a living.
But because Taylor will always be criticized for being Taylor, she included this brilliant little bit quote, these are not the complaints of a spoiled petulant child. These are the echoed sentiments of every artist, writer and producer in my social circles who are afraid to speak up [00:38:00] publicly because we admire and respect Apple so much.
She’s essentially taking the bullet and putting herself and her reputation on the line for everyone who doesn’t have the same level of influence that she does, and will continue to see this pattern of her single-handedly changing the music industry throughout the rest of her career. In response to the letter, apple quickly reversed course and began paying artists what they deserved.
This was the first time she really went head to head with the music industry, and it wouldn’t be the last. The media at this time, however, was not focused on her business acumen or her songwriting. They were too focused on sexualizing her and slut-shaming her for going out with girlfriends. There was also a lot of tabloid fodder about her sexual assault case because the DJ who assaulted her can’t let it go.
In 2015, he sues Taylor for $3 million. She counter sues for $1, and in her next era we’ll find out [00:39:00] exactly what happens
in 2016, 1989, won Best Pop album of the year at the Grammys, and Taylor became the first female artist to win album of the year twice.
But what happens when powerful women find success? The world naturally tries to tear them down. And, oh boy, they were coming for her
in 2016. Taylor wraps up her incredibly successful 1989 world tour and accepts her second album of the year, Grammy Award. We can assume that she’s still writing behind the scenes and with the two year pattern she had established, we eagerly anticipated another album this year, but later in 2016, it all comes crashing down.
Kanye West releases the song famous, which includes the lines “I feel like me and Taylor might still have sex. Why? I made that bitch famous.” Kanye was referring to the moment he stole the stage at the Vmas, hijacking Taylor’s acceptance speech. Taylor [00:40:00] publicly condemns the lyrics stating that she never consented to his use of it.
In response, Kanye West and his then wife, Kim Kardashian, released a heavily edited video of a phone call between Swift and West. The doctored footage portrays the conversation as amicable with Taylor seemingly consenting to these incredibly degrading lyrics. What happens next? Nearly destroys Taylor’s mental health and her career.
Twitter erupts with a hashtag, #TaylorSwiftisoverparty. And users copying Kim Kardashian’s use of the snake emoji portraying Taylor as a lying quote unquote snake. Remember at this time, she’s also in the middle of a lawsuit for her sexual assault case, so it must have felt like the whole world was sexualizing her and degrading her, and it was all playing out on front of the tabloids and in social media.
Later on in the Miss Americana documentary, we’ll, got to hear what Taylor did next.
When people fall out of love with you, there’s [00:41:00] nothing you can do to make them change their mind. They just don’t love you anymore. I just wanted to disappear. Nobody physically saw me for a year, and that’s what I thought they wanted.
Taylor understandably frustrated and embarrassed over not being believed. Retreats from the spotlight. She moved to London and she takes a break from the harsh world of celebrity cancellation. It seems like this time for her is an era of really deep introspection. The reason why that backlash hurt so much was because that used to be all I had.
I felt really alone. I felt really bitter. I felt like, you know, sort of a wounded animal lashing out. I figured I had to reset everything and had to deconstruct an entire belief system for my own personal sanity. I was also falling in love with someone who had a really wonderful, normal, balanced, grounded life with her disappearance.
She breaks her two year album cycle. But she never stops writing. Swifties theorized that there is a lost [00:42:00] album in this period that was supposed to have been released in 2016, which they have nicknamed Karma because this was the only time that Taylor broke her pattern. Never before and never since. It’s always been an album every two years.
But what emerges from this period where she’s hiding from the spotlight and living in another country and ruminating on fame is the masterpiece entitled reputation.
We got the first inklings that something was coming around August of 2017, but Taylor had already been pretty visible that month, um, for the first time in a long time. Her sexual assault trial got underway on August 7th, 2017, and one week later the jury found that Taylor was sexually assaulted and she won the suit being awarded a symbolic $1.
She said she was never paid by the way, but she took home so much more, a win for victims everywhere. And then just four days after her court victory on August 18th, Taylor blacks out [00:43:00] all of her social media, everything is gone. Then some CGI snakes pop up a few days later.
Finally, five days after the total blackout, she announces reputation styled in all lowercase, and she reveals the cover art, a black and white photograph of herself amidst scandalous newspaper headlines. Six days after the blackout, we got the first single look what you made me do. Now, Swifties is often called this album a Surprise drop akin to folklore and evermore, but really it wasn’t.
It was calculated and rolled out over four months. The full album drops in November of 2017, and what we didn’t get during this period of waiting was a promo tour with interviews and performances. She’s just dipping her toes back into the spotlight, but not emerging fully just yet. This sort of adds to the mystique of this album and solidifies its tagline: “There will be no further explanation, there will just be reputation.” This album was [00:44:00] heavily influenced and inspired by the controversies that made her withdraw from the spotlight and all of the patriarchal criticism she had received really throughout her career ever since she began. It seems with reputation that she’s found this new confident stance to take during her break, as the entire album seems to say, I know what you all say about me, I just no longer give a shit.
Reputation is the first album that doesn’t include hidden messages in liner notes, and I often wonder if this is the result of her emotional reset. She’s in a very private relationship holding her cards closer to her chest after some very public trauma, it is at this point that Taylor shifts to communicating with her fans in more cryptic, covert ways, and this is where clowning, as we know, it really begins in earnest. We aren’t getting obvious clues anymore, so Swifties become sleuths. We always had been, but Taylor took her game up an a notch, so we had to, [00:45:00] also. Reputation is the album that puts Taylor back in the spotlight back to the top of the charts and back to the center of the music industry where she still remains today.
The album has 15 tracks and begins with setting the tone with, are you ready for it? We were definitely ready for it, and we let the games begin. But once we really dig into the album, we can see that it has this stark duality mirroring its black and white color scheme. It’s darker tracks like, I Did Something Bad, Don’t Blame Me, Look What You Made Me Do, and This is Why We Can’t Have Nice Things bite back at her haters in the most direct and obvious way that she’s ever done. She’s not taking any more shit. She’s telling her side of the story and she’s reemerging with a tougher attitude and a badass aesthetic.
But on the flip side, reputation is simultaneously a love album. This parallel theme begins in
the second track end game, which professes that she wants this new love to be her forever Love. [00:46:00] Love might still be a game, but this time she wants to play for keeps. Don’t Blame Me introduces a new recurring metaphor: love as a drug, where she needs one more “hit” to feel okay again. She’s addicted and like any good addict, she knows exactly where to score her next high. Then we get to track five Delicate. This vulnerable track says the quiet part out loud: “my reputation’s never been worse.” With this track, we really get a peek inside her anxious and ruminating mind can love last if it begins on shaky ground.
All of the album’s central themes are wrapped up in this one song: her reputation, self-doubt, falling in love, fear of getting hurt again. But reputation also delves into overtly sexual themes, which Taylor had really never done before up until this point, but it feels fitting. She’s no longer the good country Christian girl because her reputation’s been shot.
So instead she leans in. She owns her sexuality, she portrays her own desires [00:47:00] in songs like so It Goes and Dress.
But not everything has changed thematically,as i n a few tracks, we still get to see Taylor use the very common fairytale metaphor, the recurring metaphor of her castle and her kingdom as her career, which began, uh, with long live on Fearless continues in Call it What You Want, King of My Heart, This is why we can’t have nice things. She hasn’t given up on her fairytale ending, but she seems like she’s slowly realizing that there will always be jokers dressing up as kings trying to breach the Palace Walls
reputation quickly became the bestselling album of 2017, and though we got to see her disappointment at the lack of Grammy nominations in the Miss Americana documentary, it seems as something else was happening behind the scenes that would mean really big challenges ahead. What we didn’t know at the time was that Taylor’s contract with big machine records, Scott Borchetta’s label that she signed to in [00:48:00] 2005, but that contract was due to expire reputation would be the last record she released under Big Machine, and the album’s themes would soon become in the context of the Master’s heist.
Deeply ironic.
We are gonna leave it there with reputation for now, but please come back next week where I’m gonna cover lover all the way through the torture post department. I’m Jen, thank you for being here. And please remember to check out my website, swiftly sung stories.com, where you can find all of this content and so much more, including lyrical analysis of over 250 songs, detailed lyric quizzes, analyzation of all of Taylor’s prologues, and so much more.
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That’s it for this chapter of Swiftly Sung Stories. If you enjoyed this deep dive, please don’t forget to follow, subscribe, or leave a review. It helps other Swifties find their way here. I’m Jen and I had a marvelous time reading everything with you. See you next time.
