Taylor Swift’s Career Timeline (Part 2): Lover to TTPD
Podcast Episode: October 2, 2025
Episode Description
After reputation, Taylor Swift pressed the reset button. She had a new record label, a new outlook, and set out to make a new kind of album. But it wouldn’t be all rainbows and purple-pink skies: there were storms brewing on the horizon.
This episode picks up where we left off in part 1 with the release of reputation, and we’ll explore Taylor’s career from her Lover era through The Tortured Poet’s Department. We’ll cover the pandemic years with her journey into the folklore & evermore woods, her splash back into pop music with Midnights, the re-record process with her Taylor’s Version albums, the roller coaster ride of The Eras Tour, and her introspective look at fame and identity in TTPD.
Through it all, we’ll uncover how and why her songwriting and storytelling has changed, and what it might be able to tell us about the upcoming The Life of a Showgirl.
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Episode Transcript
[00:00:00] Hey everyone. Welcome back to Swiftly Song Stories. I’m Jen. I am your Swiftie English teacher, and today we are diving into part two of the complete timeline of Taylor Swift’s career.
Just a quick note before we get started. All of this content is available on my website linked in the show notes, swiftly sung stories.com, where you can also find my English teacher analysis of over 250 of Taylor’s songs, lyric quizzes, close readings of all of her prologues, and so much more.
If you came from part one, you might already know this about me, but I don’t cover Taylor’s personal life in my work. I’m here for the work and the art, and so in this timeline, I’m not covering things like boyfriends or cheating scandals or sexuality. I’m here for the work. I’m here for the art, and if you’re into that, please gimme a like and a subscribe.
Alright, let’s dive back in.
Welcome to swiftly sung Stories where we unpack the Taylor Swift Universe one [00:01:00] era album and lyric at a time. Think of it like English class, but it’s all Taylor Swift and none of the boring stuff. I’m Jen, your Swiftie English teacher and classes in session, so come on in and meet me in the margins.
We left off last time with the release and incredible success of reputation, but what we didn’t know heading into the lover era was that something big was brewing behind the scenes. Towards the end of 2018, Taylor is wrapping up the hugely successful Reputation Stadium tour. It broke multiple attendance and revenue records sound familiar, and we can surmise that behind the scenes, Taylor is still writing away and coming up with the concept for her next album, but we didn’t know at the time was that who would produce and release That album was completely up in the air in the same month that the tour ends in November of 2018, it’s announced that she has left her home label Big Machine records for, at the time, unknown reasons.[00:02:00]
She signs a multi-year multi album deal with Republic Records, who she’s still with today. But here’s the big hangup. Her former label Big Machine Records, still owns the master recordings of her first six albums. We’d later learned that big machine offered her ownership of her master only if she resigned her contract with them, forcing her to buy back each old album by turning in a new one. We don’t get to hear the full details, though. I hope that we will someday, but we can surmise that this felt like a huge betrayal. This music is her life’s work, and she can’t own it unless she’s tethered to the label that’s holding it hostage. And on top of that, by Scott Borchetta, whom she considered as close as family, it feels like blackmail and deeply unfair.
This is what Swiftie referred to as the Master’s Heist.
But while all this is happening, she’s also stepping into a new realm of controversy using her power as a powerful political voice.
We [00:03:00] got to see behind the scenes of this new venture in the Miss Americana documentary, in which Taylor fights her team and her parents to use her voice to endorse two Democrats for the Tennessee midterm elections. She’s building a new reputation brick by brick, and coming into her own and her next album would bring this new, bold, more comfortable tailor into the spotlight, but not before many, many more people would try to silence her and tear her down.
So we’re heading into 2019. Taylor is under a new label, and in March she steps out on stage at the iHeartRadio Music Awards in a pastel sequin jumpsuit. This is a drastic change from the reputation aesthetic was was all black and white.
So we get the sense that something is coming and something is changing, and it’s gonna be very different throughout this year. She gives lots and lots of interviews and really puts herself out there. She’s more visible than she’s ever been. Then on June 1st, she introduces a [00:04:00] petition in support of the Federal Equality Act and goes head to head with Donald Trump, continuing her political activism of this era.
Then on June 13th, she announces her next album Lover to Be Released in August. The cover art previewed on Instagram is the polar opposite of reputations. It’s Taylor with a glitter heart drawn around her eye in front of a pastel huge sky. We’re getting the feeling that with the aesthetic, it’s the dawn of a new day.
The sun is rising over a new era and setting on the old one. But there are storms on the horizon, and before lover is even released, the headlines read, quote, scooter Braun acquires Scott BOA’s, big machine label group, Taylor Swift, catalog for over $300 million. On June 30th, 2019 on Tumblr, Taylor responds with this heartbreaking post.
It’s a little bit long, but I’m gonna read all of it because it’s important. For years, I asked Pleaded [00:05:00] for a chance to own my own work. Instead, I was given an opportunity to sign back up to big machine records and earn one album back at a time. One for every new one I turned in. I walked away because I knew once I signed that contract, Scott BTA would sell the label, thereby selling me and my future.
I had to make the excruciating choice to leave behind my past music I wrote on my bedroom floor and videos I dreamed up and paid for with the money I had earned. Playing in bars, then clubs, then arenas, then stadiums. Some fun facts about today’s news. I learned about scooter bronze purchase of my masters as it was announced to the world.
All I could think about was the incessant, manipulative, bullying I’ve received at his hands for years. Like when Kim Kardashian orchestrated an illegally recorded snippet of a phone call to be leaked, and then Scooter got his two clients together to bully me online about it, or when his client, Kanye West, [00:06:00] organized a revenge porn music video, which strips my body naked.
Now Scooter has stripped me of my life’s work that I wasn’t given an opportunity to buy. Essentially, my musical legacy is about to lie in the hands of someone who tried to dismantle it. This is my worst case scenario. This is what happens when you sign a deal at 15 to someone for whom the term loyalty is clearly just a contractual concept.
And when that man says music has value, he means its value is beholden to men who had no part in creating it. When I left my masters in Scott’s Hands, I made peace with the fact that he would eventually sell them. Never in my worst nightmares did I imagine the buyer would be Scooter. Anytime Scott Bacheta has heard the word scooter Braun escape my lips.
It was when I was either crying or trying not to. He knew what he did. He knew what he was doing. They both did. Controlling a woman who didn’t wanna be associated with them in perpetuity, that means [00:07:00] forever. Thankfully, I am now signed to a label that believes I should own everything that I create.
Thankfully, I left my past in Scott’s Hands and not my future. And hopefully young artists or kids with musical dreams will read this and learn about how to better protect themselves in a negotiation you deserve to own the art you make. I will always be proud of my past work, but for a healthier option lover will be out August 23rd, sad and Grossed Out Broken Heart Emoji.
Taylor. This was the first time we really got to hear what went down from Taylor’s perspective. And all this messiness and heartbreak is happening at a time where she’s meant to be promoting an album that’s about love, growth, and emotional acceptance. I imagine her at this time, on the inside still wearing reputation, black and stiletto boots, but on the outside, covered in rainbows and butterflies.
But still the lover rollout continues and on August 23rd, 2019, Taylor releases lover, the first album that she fully owns, and it [00:08:00] really is the polar opposite of reputation in all the ways it can be. In the prologue, she tells us, quote, I’ve decided that in this life I wanna be defined by the things I love, not the things I hate, not the things I’m afraid of, or the things that haunt me in the middle of the night.
Those things may be struggles, but they’re not my identity.
the album sets this tone right from the very first track. I forgot that you existed. She’s moving on from all of the drama that inspired her last album and her quote unquote cancellation and focusing on how lovely her life is now that she has a new mindset. But if I could categorize each song on Lover, I’d say it has three major themes.
Songs about falling in love, song about the pain of love, and songs about the patriarchy. Songs about falling in love include the title track Lover, I Think He Knows, Paper Rings, London Boy and Daylight, but songs about the pain of being in love include Cruel Summer, the Archer, which [00:09:00] is her track five on this album, Cornelia Street, Death by a Thousand Cuts, and Afterglow.
Her politically charged songs, which is a brand new theme for her at this point, include the Man, Miss Americana and The Heartbreak Prince, and You Need to Calm Down. We can see her trajectory changing, moving away from the things that try to bring her down and embracing the things, the positive aspects of her life. But behind the scenes things were not all purple, pink skies. While promoting Lover Taylor is invited to perform at the American Music Awards, being honored as Artist of the Decade.
She wants to perform a medley of songs from throughout her catalog in keeping with the theme of the award she’s receiving. But it wasn’t to be, she said on Tumblr in November, 2019, Scott BTA and Scooter Braun have now said that I’m not allowed to perform my old songs on television because they claim that would be rerecording my music before I’m allowed to next year.
Additionally, and this is the way I had planned on telling you this, Netflix [00:10:00] has created a documentary about my life. For the past few years, Scott and Scooter have declined the use of my older music or performance footage for this project, even though there’s no mention of either them or big machine records anywhere in the film.
Scott Borchetta told my team that they’ll allow me to use my music only if I do these things. If I agree not to rerecord copycat versions of my songs next year. Which is something I’m both legally allowed to do and looking forward to, and also told my team that I need to stop talking about him and Scooter Braun.
I feel very strongly that sharing what’s happening to me could change the awareness level for other artists and potentially help them avoid a similar fate. The message being sent to me is very clear. Basically, be a good little girl and shut up, or you’ll be punished
Early in 2020, we get to hear more about what’s going on behind all the animosity directed at Taylor when her Miss Americana documentary [00:11:00] drops in January.
If you haven’t seen it, it is a must watch required viewing for all Swifties, and it’s really the most candid we have ever seen her on screen. But you all know what happens next. It’s 2020, another storm is coming, and this time it would take out not just Taylor Swift, but the whole damn world.
We don’t get to live in the Lover era for very long before the COVID-19 pandemic canceled life as we know it, Loverfest is canceled and Taylor like the rest of the world goes into lockdown. But unlike the rest of the world, Taylor never stops working. While we were all working on sourdough and binge watching Netflix, Taylor is creating her next albums and stepping into an entirely new genre of songwriting and storytelling.
On July 23rd, 2020, just a few months into lockdown, Taylor announces her next album Folklore. Styled in all lowercase like reputation, A mere 16 hours later we’re streaming it in our homes. [00:12:00] We later find out that she didn’t even notify her new label until a few hours before it was released, which is incredible.
I think really shows us what kind of freedom she has with Republic. In stark contrast to
the controlling and manipulative relationship she seems to have had with Big Machine. Folklore is recorded piecemeal with Taylor Jack Antonoff and new collaborator, Aaron Dessner of the band, the National, all quarantined separately. But what emerges is a remarkably cohesive album that leans into folk and indie wrapped up in the themes of romanticism and escapism.
It makes sense, right? She’s not living in the real world. She’s stuck at home, so she uses her mind to escape. Without the real world to provide her inspiration. She just dreams it up herself and creates fictional worlds and fictional characters to write about. But no matter who she’s writing about, Taylor, like all great writers, uses real experienced [00:13:00] emotions to fuel her writing and folklore has emotion and abundance.
In the prologue she tells us, quote, it started with imagery, visuals that popped into my mind and peaked my curiosity. Pretty soon these images in my head grew faces or names and became characters. I found myself not only writing my own stories, but also writing about, or from the perspective of people I’ve never met, people I’ve known, or those I wish I hadn’t in isolation.
My imagination has run wild. And this album is the result. A collection of songs and stories that flowed like a stream of consciousness. Picking up a pen was my way of escaping it to fantasy history and memory. I’ve told these stories with the best of my ability with all the love, wonder and whimsy they deserve.
Now it’s up to you to pass them down.
Folklore really showcases Taylor’s storytelling at its very best and takes her craft to a new level of genius. But it also allows Taylor something that she’s always [00:14:00] been trying to do: write about her life without being lambasted for writing about her life, or having the consequences blow back on herself or on others that she writes about. Including fictional stories, but not telling us exactly which ones are fiction, is a really brilliant way to accomplish this. She can use real experiences and real emotions, but place them inside the world of a fictional character. The result is this blurred line between fact and fiction, which makes it incredibly hard to pin down what personal experiences may have inspired them, and that’s the point.
The first track on folklore is “The 1” which begins with the symbolic lines. I’m doing good. I’m on some new shit. She’s definitely on some new shit with a new sound, a new woodsy, folky aesthetic, and a new level of intricate literary lyrics. The second track, cardigan, was the first single from folklore and the only music video that we got from this album.
[00:15:00] Thematically, this track really ties the album together, juxtaposing old and new growth and stagnance, and leaving versus returning. Cardigan has two sister tracks, Betty and August, and Taylor tells us that these songs are about an imagined love triangle. The last great American dynasty is track three and showcases a new level of narrative storytelling, taking the real life story of the former owner of her Rhode Island mansion and drawing parallels between her own life and reputation. Exile is an incredible duet with new collaborator, Bon Iver, Justin Vernon. And a third mystery songwriter also entered the chat, William Bowery.
There was a huge amount of speculation as to who William Bowery was, and in the folklore Long Pond Studio Sessions documentary, we got to hear that William Bowery is Taylor’s then boyfriend, Joe Alwyn.
Her track five for this incredibly [00:16:00] vulnerable album is My Tears Ricochet, which according to the prologue is about quote, an embittered tormentor showing up at the funeral of his fallen object of obsession unquote.
But we all assume that the song is about her former label manager, Scott Borchetta. This album is a turning point in so many ways and really showcases Taylor’s songwriting as the powerful storytelling that it is. She’s no longer the glittery pop star, shifting her hips in a sequin dress. She’s so much more, she’s a thinker, an intellectual historian, a reader, and most importantly, a writer.
This is also reflected in her plethora of literary references in this album from Peter Pan to Alice in Wonderland, to Jane Eyre, to his poems by Sylvia Plath. This album is her most intertextual yet, and it’s a theme that will continue enter her future songwriting. But for me, the most important song on folklore is mirrorball in which she reflects [00:17:00] on who she really is.
We can almost see her brain churning, working through the trappings of fame and identity. Is she the glittering pop star, the born performer? What does she owe us? What do we owe her? She’ll continue to explore her relationship with her fans in future songs, but this is the first time we really get to see that she doesn’t have it all up there on her pedestal.
She’s afraid that she could fall off at any minute, and if she does fall, will the world use it as tabloid fodder? We get a glimpse behind the scenes of making this album with very candid interviews in a documentary released in November of 2020: folklore:the Long Pond studio sessions. In it, Taylor performs the album song by song accompanied by Jack Antonoff, Aaron Deser, and featuring Justin Vernon of Bon Iver.
If you haven’t watched it, you need to head over and watch it now. It is really powerful. It gives us an incredible glimpse into what her songwriting life is like and what her storytelling [00:18:00] process is.
For me, these are the most important things we get to hear. In the documentary. Taylor says, quote, this is the first album that I let go of that need to be a hundred percent autobiographical. She goes on to say, that’s my favorite thing about this album, that it’s allowed to exist on its own merit without being, oh, people are listening to this because it tells them something they could read in a tabloid.
This is Taylor acknowledging that she has painted herself into a corner. She began writing songs about her own life. Her fans soon came to expect that we’d hear the juicy details of her life in her songwriting, but that leaves so little room to branch out and flex her creativity. But with folklore, she really found a new way out and she did it brilliantly and including fictional characters and storylines she can write about her life without writing about her life.
She purposefully blurs the line between fact and fiction, muddying the water so thoroughly that we have no idea what was inspired by real life and what was inspired by her imagination. [00:19:00] It’s an absolutely brilliant move, and apparently she’s so taken with this newfound freedom that she decides to stay there in the half fictional Folklorean Woods for one more album.
On December 10th, 2020, she announces Folklores sister album Evermore. It was released the following day. She says in the evermore prologue. To put it plainly, we just couldn’t stop writing songs to try and put it more poetically. It feels like we are standing on the edge of the Folklorean woods and we had a choice to turn and go back, or to travel further into this forest of music.
We chose to wander deeper in, and my collaborators and I are proud to announce that my ninth Studio album and Folklores sister record is here. It’s called evermore. I’ve never done this in the past. I’ve always treated albums as one-off eras and moved on into planning the next one. As soon as an album was released, there was something different with folklore.
In making it, I felt less like I was departing and more like I was returning. [00:20:00] I love the escapism I found in these imaginary slash not imaginary tales. I love the way that you welcome the Dreamscapes and the tragedies and epic Tales of Love Lost and found, so I just kept writing them.
Though both albums sound very similar to me, folklore feels like it explores beginnings and messy middles. While evermore explores endings. It opens with Willow, which feels like a continuation of the cardigan story line. And this is also reflected in the music video for Willow, which actually takes place in the cardigan universe, picking up where that music video left off.
In both songs, she’s searching for a love that she can never quite grasp. In the end of the Willow Music video though, she finally gets it and walks out of the cabin, hand in hand with her partner. But there are less happy endings on evermore, too. Champagne problems sees the disintegration of a relationship through a failed proposal.
Happiness reflects on a love lost and the lessons she’s learned. Coney [00:21:00] Island narrates a slow growing apart of two people who can just never get on the same page. And Ivy details the forbidden affair of an unhappy wife. The album nears its end with closure, which is really more about not needing closure and just moving on when you’re over it.
Then the title Track Evermore closes out this album and era on a hopeful note. After wandering through this dark night of the soul, she emerges from her folklorean cabin with the realization that this pain won’t be forevermore.
She’s caught her breath. She steps out of the Folklorean woods and she emerges ready to really conquer the world. Though we had gotten confirmation that Taylor was exploring Rerecording her first 6 albums, we didn’t know what all this project entailed until she dropped the very first one on an appearance right before Lover dropped on Good Morning America.
She revealed that in November, 2020 she’d be able to rerecord albums one through five. The timeline for reputation, her sixth album was a [00:22:00] little more unclear and as that was the last album that she’d released under Big Machine and had only been released three years earlier. Through her folkmore era, she wasn’t just working on new music. She had begun rerecording her old albums one by one.
Looking back, I think we need to consider the years of COVID, the start of what is the most prolific period of Taylor’s career. In 2021, we get the first re-recorded announcement also on Good Morning America, which if you ever hear Taylor is going on Good Morning America. That. It’s gonna be an announcement.
That’s just where she does it. I don’t know why. In a video appearance on February 11th, she announces that she’s dropping Love Story, Taylor’s version that very night. She also reveals that she’s completed the entire album and Fearless Taylor’s version will be out soon. Love Story Taylor’s version jumps immediately to the top of the charts, which must have been incredibly encouraging for Taylor and her team [00:23:00] because this just wasn’t something she’d never done before.
This was something no one had ever done before. They may have rerecorded, you know, greatest hits compilations, but no artist in history had ever gone back and meticulously rerecorded each album they’d ever put out in the following weeks and months. We get Easter eggs in the form of anagrams on social media, teasing the track list.
And then on April 9th, 2021, we finally get her Fearless Taylor’s version.
Included are a whopping six vault tracks that we had never heard before. This album gets 50 million first day streams on Spotify, and when combined with folklore and evermore, she becomes the first artist to ever have three number one albums in the same year. This power move of rerecording her albums got mostly positive reviews, and here’s my absolute favorite quote about Fearless Taylor’s version.
Marie Claires, Kate Dwyer said re-recording and re-releasing six for early albums [00:24:00] is yes, a statement that artists should own the rights to their work, but something else is happening too. In reintroducing those albums, swift is divorcing her music from the sexist media narrative that followed her during her adolescence.
Inviting listeners and critics to engage with the same songs today without as much gender bias. Listeners who didn’t believe she was a feminist before, for whatever sex reason, can’t deny the feminist undertones of becoming the industry spokesperson for artist rights. The title of that Marie Claire article, by the way, is why Fearless Taylor’s version hits different in 2021, which if you know what music is to come after this album, could be a clue, or it could simply be the use of a common, modern phrase, but the journalist makes an important point.
This move is so monumental in so many ways. It solidifies our status as a cultural and industry icon. It changes the music industry and it changes the way fans think about the music they [00:25:00] consume. It changes the game for songwriters and for young artists just getting started. But one of the more overlooked aspects of the rerecord is how it affects Taylor’s relationship with her fans.
We showed her, like we always show her that we will consume literally anything she puts out into the universe, even if it’s “Me!”, which is my Swiftie ick song. What for some artists could look like a vanity project becomes this sort of shared mission for all of us. Let Taylor Swift own her music, and what we didn’t know at the time is that we would all be mobilized in the most massive and record breaking way imaginable to help her achieve this goal.
And it’s because of our passionate support that she would finally be able to achieve it. By the end of 2021, Taylor has put out a massive three albums in just 10 months, but before the year is out, she’ll put out another one. On June 18th, she releases the cover Art for Red Taylor’s version, and on August 5th she [00:26:00] releases a word puzzle that when solved, spells out the names of some of her collaborators on the album as well as the highly anticipated All Too Well Taylor’s version, 10 minute version.
This is both an inside joke and a present to her fans.
On August 6th, we get the official track listing, and there it is all too well, 10 minute version, Taylor’s version. The album clocks it in a whopping 30 tracks with eight never before heard vault tracks. It’s released on November 12th, and we don’t only get the album, she’s not done yet. We get a short film.
This song already felt cinematic even before the 10 minute version, so it’s so fitting that we get to see her bring her vision to life on the big screen.
The following day, Taylor appears on Saturday Night Live and this performance is still one of her most iconic ever. The short film is screening in the background and the stage sets include these changing weather with falling leaves [00:27:00] when it’s happening in the song, snow falling down to close out, it’s just perfection Now on SNL all musical guests usually get to perform two songs, one in the first half of the show and one in the second half of the show.
But since this is the longest song ever performed on, on SNL, she gets a 10 minute block right in the middle, and it’s just amazing. If you haven’t seen that performance, you have to go watch it immediately.
But our girl is still not done A few days after this. We also get another treat. The, I bet you can think about me, music video, the first real vault track music video that we got in this entire rerecord process. And I love this video for so many reasons, but overall, I think it just sums up the Red album so perfectly.
Touches on these themes of memory, lost love, regret, rumination, and the color red, which is of course important piece of symbolism in the album, slowly takes over the entire scene, including Taylor’s wedding dress that she wears, just really representing how this regret and rumination can wash over us, even at really inopportune moments like [00:28:00] a wedding.
Red TV absolutely takes over the charts. It breaks all the streaming records and all too. Well, 10 minute version becomes the longest number one song in history. Many, many media outlets consider Red TV to be the biggest pop culture moment of the year, and 2021 really is the year of Taylor Swift, but she’s just getting started.
There’s so much more to come.
We are now in 2022, and Taylor makes a surprise appearance at the MTV Video Music Awards. She’s nominated for Video of the year for the All Too Well short film
important to note for this short film video. It’s not only based on a song that she wrote and sang.
She’s also the writer, director, producer, and star of this film. She literally does it all. And if you haven’t seen the behind the scenes making of the short film, it’s well worth a watch. And I love that we get to see Taylor bringing her vision to life. I often think of how cathartic that must have been to take all of this pain of this toxic relationship and not only turn it into several beautiful pieces of art, but win awards for it.
It’s [00:29:00] just iconic. And wouldn’t that be amazing if we could all turn our worst relationships, our worst failures, our worst pain into just these giant successes? God, I wish we could all do that.
It’s truly masterful. But she wasn’t done yet. She still had one more surprise for us at the VMAs.
‘
I, I thought it might be a fun moment to tell you
that,
that my brand new album comes out October 21st. After this announcement, all of her socials, her website, her Spotify images are updated to only a picture of a clock keeping in time with the theme of the album. Sorry, I couldn’t resist that one. On September 21st, she debut her TikTok series, midnight’s Mayhem with Me, series of videos in which she pulls numbered bingo balls out of a lottery spinner, and tells us the track list one by one, speaking into an old rotary phone.
By the end we have 13 tracks. There’s that [00:30:00] lucky number again, but in some of the videos, she’s holding this phone upside down and that combined with the clock imagery have Swiftie in a complete tailspin clowning for what we’re gonna get once the clock strikes midnight.
unlike the extensive promo tour that lover had, midnights is pretty quiet in that department. She’s visible on social media, but doesn’t do any in-person interviews for the album. We are eagerly anticipating this drop, and we finally get to hear it at midnight on October 21st, 2022. There are indeed 13 songs on this album, but just three hours after midnight at 3:00 AM we get a surprise, the 3:00 AM edition with seven additional songs.
Later on, while she’s on The Eras tour, she will release yet another edition, the Till dawn edition that contains three more songs bringing the total to 23. Taylor receives a lot of flack for this strategy and, and always has of releasing multiple records and multiple versions, and I [00:31:00] understand where it’s coming from in terms of consumerism over consumption.
it’s just economics. It’s supply and demand. She wouldn’t be able to do this if her fans wouldn’t eat it up. And we do, and I say this as a person who doesn’t buy physical albums from anyone anymore, but I can see why you would want to, and I could see why she would do it.
The Midnights album left the metaphorical “folkmore” Woods, with its more gentle indie vibes, and it moves directly back into pop. But she’s still maintaining this really intricate storytelling and songwriting that she leaned into during Isolation. Midnights is also a concept album similar to Speak Now, which was about things left un said throughout her life.
She tells us in the prologue, this is a collection of music written in the middle of the night on a journey through terrors and sweet dreams. The floors we pace and the demons we face for all of us who have tossed and turned and decided to keep the lanterns lit and go searching, [00:32:00] hoping that maybe when the clock strike 12, we’ll meet ourselves.
What this concept album does is really clever and it’s strategic. It allows her to write about her life without writing about her current life. Similar to the pseudo fictional world of folklore and evermore, it gives her some breathing room to express her emotions without being lambasted for expressing her emotions.
These things might have kept her up at night, but it doesn’t mean they’re still keeping her up. It’s this anthology of restlessness and regret and falling in and outta love and self-doubt and ruminations.
But what it does is allow her to sing about other points in her life and essentially confuse us. This might not be about her current life, this might be about something in the past. Therefore, we can’t point to anyone particular person who these songs are about. The lead single and the first music video that we got from Midnights is Anti-Hero, and similar to the tongue in cheek satire of blank space, the song [00:33:00] sees Taylor bite back at her detractors by leaning in.
I’m the problem. It’s me. She says, because it couldn’t be the patriarchy, right? It has to be the intelligent, successful, beautiful woman who is always in the wrong.
We also got a sparkling music video for Bejeweled, a song in which she won’t let anyone dim her shine. And the music video takes us into a Cinderella world where Taylor goes from scrubbing floors to getting all dolled up for the ball, winning the prince, and then kicking him swiftly out of the castle. And it zooms out on Taylor in her castle with her dragons circling around protecting her.
Some other really notable songs on Midnights are maroon, which takes all of her red tinged memories and balls them into this array of blood red regret. You’re on your own kid, is her track five in which she learns that she has always been singular and she’s always been the only one who can save herself.
It’s from this song that we get the iconic line, make the friendship bracelets [00:34:00] take the moment and taste it, which would become such an important real life aspect of The Eras Tour. But for me, the most crucial tracks come from the 3:00 AM edition. Dear Reader, takes the iconic line from Jane Eyre and applies it to Taylor’s celebrity and massive fandom
In this track, she breaks the fourth wall and tells us directly, I am no one you should emulate. I have no idea what I’m doing, and I’m falling apart, which foreshadows a lot of the themes and topics to come on her next album. Hits different, closes out the 3:00 AM edition, and it’s from this point that we will pick up in the tortured poets department.
That song details a love and a loss. That’s impossible to get over because this person is just so special and singular. But in the third verse, she says, I heard your key turn in the door, down the hallway. Is that your key in the door? Is it okay? Is it you? Or have they come to take me away? She wonders if they’re about to haul off to the asylum, which we know, will begin where [00:35:00] Fortnight picks up in TTPD.
This completely foreshadows Fortnight in which we will learn. Uh, I was supposed to be sent away, but they forgot to come and get me.
But because Taylor wasn’t doing enough, releasing four albums in less than two years and producing and directing music videos and short films, and winning all the awards and continuing her prolific songwriting, she had another treat in store for us. November 11th, 2022, just a few weeks after midnight was released, she appeared on Good Morning America.
I’m going back on tour. Uh, the tour is called the ERAS Tour, and it’s a journey through all of my musical eras of my career.
From the jump, we knew that this was going to be big. Taylor hadn’t toured since reputation, and that left the album’s lover folklore evermore and midnights that had never been performed on tour. And it was also going to include her first six albums too. That’s a catalog of 11 albums plus two Taylor’s versions already released to include in one single show.[00:36:00]
How was she gonna pull this off? She is Taylor Swift and her team is nothing but incredible. We knew it was gonna be epic. It wasn’t only gonna be the ticket of the year, it was gonna be the ticket of the decade, maybe the ticket of the century, but it was those tickets themselves that were nearly impossible to get.
The demon that is. Ticketmaster allowed bots and scalpers to purchase large groups of tickets, which resulted in tickets on resale platforms almost immediately, for exorbitant prices though, Taylor’s team declined to allow ticket platforms to use dynamic pricing, which is basically like. Uber’s, uh, surge pricing.
It’s the same thing for tickets. Resale prices just skyrocketed. Taylor did have a loyalty program of sorts kind of installed, which allowed fans to pre-register for the sale and get priority. And those who had tickets to Lover Fest also got priority for purchasing Eras Tour tickets.
But for so many of us, we just weren’t going to get a [00:37:00] ticket. We didn’t get the pre-sale code even after submitting many, many times and many different emails for it. So if you were like me and you didn’t get to go in person, even though I had something like eight shows here in my city, um. I sympathize. I empathize with you.
We form a, I didn’t go to The Eras Tour Club together. I’m here for you.
The demand and the pricing left so many of us out, and it was pretty devastating, especially once we got on that live stream and saw what an incredible show it was. We can imagine that between the time Midnights was released and The Eras Tour began, Taylor was just working her ass off. This show would be a whopping three hours and 15 minutes, and she would need an incredible amount of vocal and physical endurance.
But all that hard work paid off. And then some. The show opened in March 17th at 2023 in Glendale, Arizona, and we were greeted to a very unique stage shape. More on that leader [00:38:00] because it becomes important.
These massive digital displays and intricate lighting, a million glittering costume changes. 15 incredible backup dancers who would become famous in their own right, plus her usual band and LED wristbands that lit up and change color with the changing scenery. It was quite literally the greatest show on earth like Broadway, come to life inside a football stadium.
Because she is Taylor Swift. The show told a cohesive story from beginning to end, and though the set list changed over her 18 months of performances, it really told a cohesive story. She really is an alter ego of herself in each act and the scenes transition from one to the next Flawlessly, she begins as Miss Americana greeting and getting the fans involved right from the start.
We belt out the bridge to cruel summer and slow dance along to lover. Then she disappears under the stage and emerges as a fresh-faced country ingenue for her fearless era.
She is young, carefree, and [00:39:00] heartbroken in her red graphic tea and hat, a sparkling fairytale princess, and speak. Now she is the bad girl in reputation. A witchy mad woman in folk, Lauren Evermore, a Pop-Tart princess. In 1989, a woman scorned an out for vengeance in the tortured pose department and a sparkling diamond lighting up the night in midnights.
But Taylor also appeared as herself every night, and this came in the surprise song set. Each night, she treated us to an acoustic version of whatever songs she felt like playing one on guitar and then one on piano. She even offered commentary about her songs during this set about her life, about the tour, and about her fans.
Though she was still Taylor the performer for a moment each night, she let that mask slip a little bit and offered us a look at her real self, not an alter ego, hidden behind costume changes and elaborate sets. Throughout the length of The Eras Tour, The Swiftie fandom really changed.
We took clowning to a [00:40:00] whole new level.
We live streamed each event, uh, no matter what time zone we were in peering through this iPhone lens of whatever concert goer was kind enough to stream for us. Apps popped up where we could vote on predicted costume changes, surprise songs, and what our favorite backup dancer Kam would say into the mic during 22.
All of these moments brought Swifties together in ways we had never been before. For those who got to attend the show in person, your night is marked with what surprise songs you got. Those who got highly coveted deep cut tracks got the most bragging rights. Those who got extra special guests got extra bragging rights.
We became like football fanatics – though the patriarchy never calls men who paint their beer bellies get drunk and get into fights on the sidelines “culty” or “crazy”. If we’re a cult, we are the happiest, most loving cult there ever was, and I have no intention of leaving anytime soon. The Eras Tour was our Super Bowl and one can only hope [00:41:00] that we’ll get another chance to see Taylor live, though she set the bar so high for herself, I can’t imagine what kind of tour would happen next.
On May 5th, 2023 at her first show in Nashville, Taylor gave us yet another surprise, speak now, Taylor’s version. It was released on July 7th. A deluxe version contained two live tracks recorded right there on The Eras Tour. Speak now. Taylor’s version contained six vault tracks and we got a music video from one of them.
I can see you in the video. Taylor is locked in a vault as her younger self with her long curly locks lyrics written down her arms, and 13 stamped on her hand just like she used to do With her locked in the vault is a painting of herself, and this whole scene sort of represents the, the vault tracks, her masters being held hostage really by Scooter Braun. In the end, a tactical team pulls off the explosive heist and Taylor escapes with her painting AKA herself and her [00:42:00] work. Later on in the tour, we got another even more highly anticipated rerecord 1989 Taylor’s version on August 9th, last night in La Taylor announced 1989 TV would be released on October 27th, exactly nine years after its original release.
But before we get 1989 tv, she had yet another surprise for us On October 13th, lucky 13, the concert film, Taylor Swift. The Eras Tour premiered in theaters worldwide.
We got to see a star studded red carpet premiere, and for fans who couldn’t spend hundreds on an eras tour ticket, it was really a treat to be able to still be a part of it. We got to go to the theater and experience a piece of the hes tour for a heck of a lot cheaper. But what the most notable thing is about this film is that Taylor bypassed traditional film rollouts schemes.
She partnered directly with theaters to distribute the movies, and she set the prices herself. $19 and 89 cents for adults and $13 and 13 cents for [00:43:00] kids. She also encourages us all to treat the film like the concert itself, to get up to dance, to sing along, to take photos, take videos. It was as close as some of us could get to being on the actual eras tour.
Two weeks after the film premiered, we got 1989 Taylor’s version, which included five never before heard Vault tracks. For me, the most potent and most important of these is “Slut!”, which says the quiet part out loud. 1989 was really a product of slut shaming, which she revealed in the Taylor’s version prologue for the album.
She was trying to change her behavior to quiet the incessant criticism, but it didn’t work. So what “Slut!” does is confronts that sexism blatantly. We didn’t get any music videos for Taylor’s version of 1989 because Lord knows she was working hard enough at that point, but soon we would learn exactly what she was up to when she wasn’t on the eras tour stage and it was something big.
We are [00:44:00] now into February of 2024 at Midnights is up for several Grammy awards. At the show, Taylor wins her 13th Grammy for her best Pop vocal album, and when she takes the stage, she’s got some tricks up her sleeve.
So I wanna say thank you to the fans by telling you a secret that I’ve been keeping from you for the last two years, which is that my
brand new album comes out April 19th. It’s called. It’s called the Tortured Poets Department.
I think all swifties were taken aback by the title,
but when you combine it with Taylor’s aesthetic that night, we could tell exactly where she was headed: into a moody Long Night of the Soul set
To music. We got the track listing the next day, and anticipation for its April 19th release was rising. When it finally dropped, [00:45:00] we were greeted with 16 songs, but then we got another surprise just two hours later.
An extended version dubbed the anthology with an additional 15 tracks brought a massive total of 31 songs. Not only was this a double album, but we got Double Prologues. Stevie Nicks wrote a prologue poem entitled for T and Me, which sets the tone for the entire album, heartbreak. A Boy who Can’t See a Girl for who she is and what she’s worth.
And then Taylor, as she always does, wrote a prologue poem entitled In Summation.
Taylor also wrote a prologue, but this time it was in the form of poetry. In summation, was her prologue poem for TTPD, and as the theme of the album is Tortured Poets, the prologue is naturally a poem. It is incredibly vulnerable and expansive. I will fully dissect this poem in a later video, but here’s what I [00:46:00] see as the crucial piece quote, and so I enter into evidence my tarnish coat of arms.
My muses acquired like bruises. My towel is mins and charms. The tick, tick, tick of love bombs my veins of pitch black ink, all’s fair in love and poetry. This doesn’t just explain the contents of the album. It solidifies Taylor as what she is. She’s a poet, a writer, an artist.
She may be in glittery dresses, shaking her hips on stage, but who she is at her core is so much more. TTPD explores more than any other album ever has. The duality between Taylor Swift Inc. And Taylor Swift, the human.
In songs like, “But Daddy, I love him,” “Who’s afraid of little old me?”, “I can do it with a broken heart,” “Clara Bow,” “the albatross,” “I hate it here” and “the manuscript,” she is looking back over her life and wondering how she got here. What does it mean to be the most recognizable person on [00:47:00] the planet, but have no one really know you?
And how she built this career brick by brick until she boxed herself in. The other half of the anthology, though, wrestles with raw and really vulnerable heartbreak. At the time of writing this album, she had broken up with her longtime partner, had a short-lived and highly criticized fling with another musician.
She was more visible than she had ever been having released three studio albums and four Taylor’s versions albums in the past few years. She put out two films and barked on a major world tour. She was on this pedestal, and as we all know, people throw rocks at things at shine. The whole of TTPD seems to be wrestling with this identity, with partnership, with fame, how to find true kinship when you are a tortured artist, and everything is copy.
This album got pretty mixed reviews, but Swifties lapped it up. We loved this [00:48:00] more literary side of Taylor that she had been steering towards for a long time, but finally culminated in this album. We love diving into these intricate lyrics, and personally, I think it’s one of the most vulnerable albums she’s ever written.
It really shows how her songwriting has progressed through all of these various influences and stages of her life. This album also includes more specific literary references than ever before, and you can take a look at those on my website and we will dive into more of them in a future book club that I’m putting together.
But with the album out, and the tour is still going on, there is this big question, would the tortured post department be added to the eras tour set list?
We got to find out at her first show back from a break in May of 2024 at her first show in PEras. We were greeted with a brand new act, “Female Rage, the Musical,” after the 1989 set and before the acoustics surprise song set, Taylor popped out of the stage in a [00:49:00] crinkled white dress with lyrics scrawled on the skirt, which can’t help remind us of All Too Well, “I’m a crumpled up piece of paper lying here”, by the way.
But just like the entire Eras tour set list tells a story, the order in which she performs songs from TTPD also tells a story. It mirrors this rise and fall of a relationship and goes through all the stages of grief. She begins with, but Daddy, I love him. And so high school in this carefree world of falling in love.
Then we shift into rage with who’s afraid of little old me. Then it falls apart in town bad, she looks back and reflects on what she lost. With Fortnight then gets into the anger phase of grief with the smallest man who ever lived. Then in the last song of the TTPD set, she picks herself up. And puts on a smile for, I can do it with a broken heart.
It is a masterclass in storytelling and sums up the highs and lows of this album so well. In June during [00:50:00] her first stint at Wembley Stadium here in London, we got an extra big surprise during the TTPD set.
Her boyfriend, Travis Kelsey, waltzed out on stage and performed I can do it with a broken heart with her. He picks Taylor up off the stage after the smallest man who ever lives brings her to a sofa and they perform this vaudeville like skit to get her ready to go back out on stage when all she wants to do is lay down and have a drink.
This moment is so iconic, but it’s also important for a few different reasons. First, she’d never been in a relationship this public before. to have your partner come up on stage with you, it brings these two Taylor Swift’s and intersects ’em into one.
Those two had never been combined together in the public eye. Taylor Swift, Inc. And Taylor Swift, the human who has personal relationships.
At least they’d never purposefully intersected by Taylor before. And two, it’s symbolic. He picks her up and carries her across stage to get ready for what’s next. [00:51:00] But even though it’s comedy and it’s satire, it’s what it represents. He’s there basically as an assistant. He’s saying, you can do it, and I believe in you.
But what happens next? She does entirely on her own. He can help pick her up, but he’s not the reason. She goes on to perform. She goes on to perform because that’s the core of who she is to me. This all shows incredible growth, both in her relationship with fame and in her willingness to share her private life with her fans.
She’s really writing her own rules about her life and her business, and she truly is fresh out the slammer, running with her dress unbutton, and she’s doing it with a broken heart that seems to be slowly but surely healing from the tumultuous last few years.
The Eras tour wrapped up in December of 2024, and we collectively mourned the loss of this incredible 18 months of shows. The Eras tour really gave us hope at a time when [00:52:00] nothing felt hopeful. It brought us joy at a time when the world felt joyless and it distracted us with good things when there was really nothing good happening.
Taylor took her final bow in her glittering karma coat on December 8th in Vancouver, and although it really felt like the end of an era, we were still left with some lingering questions. Toward the end of the tour, Swifties were clowning so hard for reputation TV and debut TV that we absolutely lost the plot.
I think we all assumed that the end of the ERA’S tour would also mean the end of the rerecord era. That it wasn’t to be the first half of 2025 was pretty quiet, and we hadn’t seen a lot of Taylor.
But then on May 30th, 2025, her silence was broken and an incredibly happy announcement was posted on her website. It told us that the battle was over and the war was won.
Said in the letter, I’m trying to gather my thoughts into [00:53:00] something coherent, but right now my mind is just a slideshow, a flashback sequence of all the times I daydreamed about, wished for and pined a way for a chance to get to tell you this news. All the times I was this close, reaching out for it, only for it to fall through.
I almost stopped thinking it could ever happen after 20 years of having the carrot dangled and then yanked away, but that’s all in the past now. I’ve been bursting into tears of joy at random intervals ever since I found out that this is really happening. I really get to say these words. All of the music I’ve ever made now belongs to me Swifties the world over cried tears of joy right alongside Taylor.
And this news wasn’t just about a billionaire spending millions, not, not to us. It was the culmination of years of turmoil and accusations and bickering and planning and scheming and meticulously rerecording and endlessly performing. [00:54:00] It’s also a symbolic takedown of the patriarchy and a victory for women everywhere.
No one gets to tell us what we are worth, what our labor is worth, what our creativity is worth. We have value. In the letter she went on to say, to say that this is my greatest dream come true, is actually being pretty reserved about it to my fans. You know, how important this has been to me. So much so that I meticulously
re-recorded and re-released four of my albums calling them Taylor’s version. The passionate support you showed those albums and the success story you turned the Eras tour into is why I was able to buy back my music. I can’t thank you enough for helping me to reunite me with this art that I’ve dedicated my life to, but have never owned until now.
To put it simply because she made so much money from the the Eras Tour and the rerecord, she was finally be able to buy back her masters. It’s also because she purposefully devalued her own work by rerecording it and making the originals moot that she was [00:55:00] able to pay that hefty price tag, which we don’t get to know the numbers on, and we might maybe eventually, but it’s here that we need to remember that one Easter egg that she left us while on the Eras tour.
Remember the shape of the Eras tour stage. Maybe a keyhole or maybe a key, depending on which way your brain interprets it. The ERAS tour was the key to unlocking the vault where Taylor’s music and life’s work was locked away. Some people on social media have pointed out the Eras Tour was the biggest and best fundraiser we’ve ever contributed to, but Taylor really knew what we wanted to hear.
She also addressed what we’d all been wondering. I know, I know. What about rep tv? Full transparency. I haven’t even rerecorded a quarter of it. The reputation album was so specific to that time in my life, and I kept hitting a point. I kept hitting a stopping point when I tried to remake it. All that defiance, all that longing to be understood while feeling purposefully misunderstood, [00:56:00] that desperate hope, that shame born snarl and mischief.
To be perfectly honest, it’s the one album in those first six that I thought couldn’t be improved upon by redoing it. Not the music or the photos or the videos, so I kept putting it off. There will be a time if you’re into the idea for the unreleased ball tracks from that album to Hatch. I’ve already completely rerecorded my entire debut album, and I really love the way it sounds.
Now, those two albums can still have their moments to reemerge when the time is right, if that would be something you guys would be excited about. But if it happens, it won’t be from a place of sadness and longing for what I wish I could have. It will just be a celebration. as we continue on into 2025, nothing is for sure about the future of Taylor’s career, but I’m very excited to see Taylor Swift Taylor’s version because I think it will bring us really to this full circle moment and we’ll close out this chapter with a big bow.
But if Taylor continues her two year album cycle, we can expect an announcement of TS 12 late this [00:57:00] year or early next year and we have had a few Easter eggs pointing us to the number 12, including in that letter that I just read to you where there are 12 i’s in “thiiiiiiiiiiiis close”.
There’s also the lingering question of whether the Eras tour film will be updated with the TTPD set and whether we’ll get a live album of any sort. But for now, my God, we have a lot of content to consume and I hope Taylor is taking a nice long break. We know she never stops writing though, and the world has brought an incredible amount of inspiration this year, the presidential election in America, a new relationship, a supposed feud with a friend, and most importantly, the reclamation of her life’s work.
In the rest of Taylor Swift 1 0 1, we’re gonna dive deep into Taylor’s songwriting. So I hope that this very [00:58:00] long-winded synopsis of her career has laid a good foundation for understanding her storytelling and the most important events that have inspired and challenged her.
If you want to keep up to date with everything that I create, please like, and subscribe if you could leave a review, pretty please. ’cause I’m brand new to all of this. I’ve been writing for years and years, but never put my face and my voice out on the internet and it’s terrifying.
So, uh, that would help. I would appreciate it. Um. Please stay tuned for more. I’m so excited to dive into what we’re gonna talk about next. I’ll see you next time.
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.
