The Tragic Triumph Of Taylor Swift - Part 2

While Taylor Swift may be sitting on top of the world right now, her path to this level of success has been a for more tragic one than most are willing to admit.

This is the second installment in a 3-part series on Taylor Swift. You can read the first installment here.

For what will it profit a man if he gains the whole world, and loses his own soul? Mark 8:36

Looking at Taylor Swift today, it would be easy to assume her life has simply been one long triumph after another - and to a certain degree, it has been. That being said, that doesn’t mean her path has been an easy one - far from it. Rather, her path has been a series of steps that have been carefully planned and guided by any number of wise, yet largely invisible counselors. To be sure, her parents played a large role in her ascension, but they could not simultaneously help her achieve the position she holds today and protect her from the painful events that led her to where she is today.

I believe Swift’s story is incredibly important, however, particularly to women. While it has never actually been impossible for women to rise to positions of power, too often they have done so the same many men before them have, for which they paid a terrible price. Elizabeth Holmes chose a path that wasn’t significantly different than that of Travis Kalanick (Uber) or Adam Neumann (WeWork), yet Holmes ended up in jail, whereas Kalanick and Neumann were given lucrative golden parachutes.

The truth is that as women, we know that men can “get away” with things we can’t, and yet - is that really all we want? To “get away” with things the way men do? And do they really “get away” with anything? I believe that ultimately, the truth always comes out and while men like Bill Cosby and Harvey Weinstein may succeed for a time, ultimately it is the thing that is most important to them - their legacy - that ends up in flames. I believe that Taylor Swift has chosen a very different path. One that is not only brining her current success but one that will create a lasting legacy. One we can all learn from.

Step Two: Rinse and Repeat

In November 2008, Swift released her second studio album, Fearless, when she was 18 years old. This time around, she penned seven of the album’s 13 tracks by herself and enjoyed a co-producer credit with Nathan Chapman. As mentioned in part one, this gives additional credibility to the idea that the reason Swift fought for Chapman to be her producer was because he likely listened to her and viewed their working relationship as more of a partnership, rather than trying to imprint his own vision and style on her music the way more experienced producers would have.

Her instincts paid off and the album spent 11 weeks at the top of the Billboard 200 and reached top five on charts in Australia, Canada, New Zealand, and the U.K., achieving multi-platinum certifications and spawning five chart-topping singles. The first single, Love Story, peaked at number four on the Billboard Hot 100, but was the first country song ever to hit number one on the Mainstream Top 40. Anecdotally, Swift wrote Love Story in her room in just 20 minutes after a fight with her parents over a boy she liked but they didn’t.

This anecdote, repeated several times by multiple parties, provides a key clue to some of the challenges surrounding not only Swift’s transition from adolescence to adulthood, but also her challenges within the music industry. Particularly considering the massive influence conservative Evangelical Christianity has in Nashville. As a professed Christian herself, it’s important to understand that Swift came of age in arguably the Evangelical capital of the United States right at the peak of purity culture.

Joshua Harris’s massively influential book I Kissed Dating Goodbye was first published in 1997, but would have taken a few years to reach peak cultural relevance, In fact, an updated version was published in 2003, which coincided directly with the rise of the True Love Waits campaign. During this time, many of Swift’s peers and direct cultural influences made public their commitments to purity, including Selena Gomez, Miley Cyrus, Demi Lovato and Jessica Simpson, who was a huge star at the time. Another group of high profile figures that would make public purity pledges were the Jonas Brothers, one of whom Swift would eventually be linked to.

The other interesting fact about Love Story is that while it draws thematically from Shakespeare’s Romeo and Juliet, Swift chose a happy ending for her song, rather than the tragic ending Shakespeare was well known for. These facts not only encapsulate the challenges of Swift’s career but also provide critical clues to why she has achieved such global dominance. Around this same time, numerous female pop stars were making the transition from child star to adult singer, but in every instance they were promoted in a highly sexualized fashion. In most cases, they claimed that it was their own idea, but it’s also fair to say that they were highly influenced by the culture they were a part of.

Female stars like Amy Grant and Sandi Patti rose to prominence in Nashville by singing contemporary Christian music, which allowed them to avoid being marketed in a sexualized fashion. There is and will always be a market for women singing about God and Jesus, particularly if they are wholesome, but not overly attractive in a sexual way. Jessica Simpson, for instance, originally got her start by producing a gospel album but was rejected by Christian music labels specifically for being too sexy. In Evangelical parlance, her curvy figure would “cause guys to lust.” It was directly into this vacuum that Swift was dropped.

She wasn’t a Christian artist, who could be marketed without selling her sexuality, but she was trying to make her way in an industry that doesn’t seem to know what to do with women that aren’t particularly interested in selling their sexuality. Swift was attempting to sell something that no woman had yet managed to commercialize. By writing her own music, she was attempting to sell her voice, her thoughts and her music, period. And, as it turns out, there is actually a rather large market for those things. Particularly when she isn’t singing songs predominantly written by men.

Most songs are written by songwriters and then shopped around to various artists and labels. In many cases, the artists themselves don’t even choose the songs they record, they are chosen for them by their labels. These songs speak to common situations many people find themselves in, but are also relatively impersonal to the musician. Swift, however, wrote about her personal and individual experiences. Experiences which also happened to resonate with a large number of girls and even a growing number of boys and young men.

Even critics acknowledged that her songs actually reached a much broader audience than most teen pop sensations. Although Love Story was at first panned for being somewhat shallow thematically, it would eventually come to be not only one of her top grossing singles, but also one of her best. Swift’s music was a reflection of her life experiences. As she grew and matured so did her music and lyrics. Although in her late teens Swift was still largely writing about romantic relationships, an event was quickly approaching that would shatter the innocence from which Love Story sprang.

Step Three: Into The Octagon

September 13, 2009 was a day that would go down in infamy in Swift’s young life. That night, at the Video Music Awards, she was awarded the Best Female Video award for her song “You Belong With Me.” Also nominated in that same category was Beyoncé’s video for “Single Ladies (Put a Ring on It).”

As Swift stepped forward to give her acceptance speech, however, she only got a few words out before a then 32-year old Kanye West jumped on the stage, grabbed the mic, and shouted, “Yo, Taylor, I’m really happy for you and I’mma let you finish, but Beyoncé had one of the best videos of all time. One of the best videos of all time!” That moment was the start of a saga that would last for decades. One which would eventually bring the young star to one of the blackest periods of her life, but also create perhaps one of the biggest opportunities of her life as well.

Soon after Swift won her award, Beyoncé actually won a much larger acccolade for her video, the Video of the Year award. While there is some question as to whether Beyoncé’s next actions were her own idea or whether she was pressured into it by the show’s producers, ultimately, Beyoncé graciously invited Swift to come up and finish her acceptance speech. That moment marked the beginning of a long, although often tumultuous relationship between the two stars. In fact, it was actually that relationship, rather than the initial incident with West that would lead to a decades long feud not just with West himself but with his future wife Kim Kardashian.

What is interesting, however, is how West would go on to paint himself not as the perpetrator of a great wrongdoing, but the victim. Another interesting dynamic is that this nomination was for best female video, for which West was not a nominee, but he was nominated for best video of the year, which he ultimately lost to Beyoncé. What makes this interesting is that he clearly felt Beyoncé deserved best female video, but my guess is he was neither pleased and, quite frankly, never expected to lose to Beyoncé for best video of the year. All in all, it was an event that would reverberate over the next two decades of all three careers.

The following year, Swift released her third album Speak Now, on which she wrote every track. Although several tracks were still oriented towards romantic relationships, they also showed a growing maturity in her understanding of the world, and what a dark and ugly place it can actually be. The song Innocent, is largely believed to be about the incident with West and she has openly stated that the track Mean is about the constant criticism of a specific reporter that seemed to just hate her and caused her considerable pain.

Like most of her albums, Speak Now also contained a few tracks that are reputed to be about certain relationships she had during that time. Back to December is largely considered to be about her relationship with actor Taylor Lautner. The song is a remorseful plea for forgiveness, in which she seems to display a recognition that sometimes she herself might actually sometimes be the one with problematic behaviors in a relationship. Although their romantic relationship did not last, Swift and Lautner remained friends and he even appeared in her 2023 music video for her song “I Can See You.”

Her hit single Mine is alleged to be about her relationship with Glee star Cory Monteith, whose life would later be cut short by a heroine overdose. Her song Dear John is also reputed to be about singer John Mayer, whom she dated when she was just 20 years old. He was 32 at the time. In the song, she sings about a man who displays a number of problematic behaviors, and asks “Don't you think I was too young to be messed with?”

Meanwhile, in 2010, Kanye West appeared on the Ellen DeGeneres show and stated that following the incident with Swift and the subsequent public outcry, he basically had to leave the country and stay overseas for a time. Rather than accepting the public response as being appropriate to his actions, he presented himself as a Social Justice Warrior valiantly fighting the culture wars and being punished for his heroism. Which is to say, he presented himself as a victim rather than an aggressor. A narrative that seemed to late be accepted by the general public, even though it is clear it was his actions that were truly egregious.

During this time, Swift was also developing an ongoing friendship with Beyoncé, who is married to media mogul Jay Z, who (not surprisingly) was not only friends with West, but also produced several of his albums on his imprint Roc-A-Fella records. Almost assuredly at their urging, Swift eventually tried to mend fences with West. In 2012, she appeared in Australian Harper’s Bazaar wearing a shirt from West’s clothing label. That same year, she also released her fourth studio album, Red.

While Red didn’t quite complete her transition from country artist to pop star, it was certainly another step in her journey far beyond the bounds of country music. In fact, it would be fair to say that her most recent album The Tortured Poet’s Department has even moved her beyond the bounds of mere “pop” stardom. On Red, Swift moves past the glitter and sparkle of teen romances and begins to delve into the much deeper and painful emotions of fully adult relationships.

Most of the songs on her album were ostensibly written about one relationship in particular, which is regularly considered to be with Jake Gyllenhaal. In spite of having nearly the same age gap between herself and Gyllenhaal as with John Mayer, the songs she theoretically wrote about Gyllenhaal definitely don't have the same accusatory tone as Dear John. Aside, perhaps, from the single “We Are Never, Ever Getting Back Together.” That, however, may be attributable to a factor that has nothing to do with either party in the relationship, but rather a third, highly intrusive element.

Her relationship with Gyllenhaal largely marks the start of what would become an ongoing theme in many of her future relationships. Gyllenhaal himself has remarked how very difficult it is to build a relationship in the blinding glare of the spotlight Swift is forced to live in. It is ironic that she is so often criticized for jumping from relationship to relationship, when in actuality it may well be the intense scrutiny to which all of her relationships are exposed to that often leads to their demise far more than her own actions. It may well be that Gyllenhaal had a greater interest in Swift than either she or the media want to give him credit for, but just couldn’t handle the significantly greater intrusion of press and paparazzi that she brought with her than he himself was subjected to at his own level of fame.

Meanwhile, in a 2013 interview with the New York Times, Kanye West not only revealed that he had absolutely no regret (or remorse) for interrupting Swift, but also that any time he does not receive an accolade, award (or spot on the team), it’s an injustice. It is during this time that the lore around the infamous Swift/ West incident is slowly being rewritten. While West is slowly being platformed for ostensibly “standing up” to the pop star, she is slowly being panned for attempts to make light of the matter. In other words, his role as victim and her role as villain is slowly but steadily becoming cemented in the zeitgeist, even though Swift literally did nothing to West. Just a month after West’s interview, Swift is essentially publicly scolded for not “letting things go” when she sends Ed Sheeran a jar of homemade jam, with a label seeming to mock the infamous moment.

in 2014, Swift moved from Nashville to New York and began work on what would be her first official pop album. She also officially began what would become a decades-long working relationship with producer Jack Antonoff. Although Antonoff had previously produced her single Sweeter Than Fiction for the film One Chance he produced three tracks on 1989. Antonoff has frequently credited Swift as fighting for him, the same way she did with Nathan Chapman. Like Chapman, Antonoff would help her record rough cuts of songs, following which, the studio would then want her to work with a “real” producer to create the final album versions. She instead, fought to have Antonoff produce the final album cuts and eventually, she won.

On 1989, Swift also expanded her songwriting to focus on her larger relationships with the public, as opposed to just her romantic or intimate ones. Most notably, both her hit singles Shake It Off and Blank Space deal with all of the media rumors and speculation she is constantly subjected to both in her personal and private life. Ironically, while her single Bad Blood is frequently attributed to some kind of dispute with Katy Perry, there is a very good chance it is instead about betrayal in a relationship. One of the biggest problems with the scrutiny on Swift from both the media and fans, is that it leads to the belief that they actually know everything about her life, including every man she has ever dated. In fact, she has almost assuredly had a number of relationships that neither the media nor fans ever know about.

And this is largely the source of her power that few seem to understand.

Although the inspiration for some of her songs may seem to be more obvious than others, Swift herself has never confirmed nor denied who exactly they are about. The beauty of this is that every person she has ever written a song about almost assuredly knows it is about them, but there isn’t much they can do about it if the exact nature of their relationship is not publicly known. While the subject of her songs may have to spend every day for months hearing the song written about them, they can’t protest it without subsequently inviting a massive amount of scrutiny from a fan base determined to know why it was written about them.

2014 was a big year for Swift. In addition to being named Billboard's Woman of the Year (the first artist to win the award twice), she also received the the inaugural Dick Clark Award for Excellence at that year’s American Music Awards. It was also during this time that Swift began her battle with the app industry that often made more money from music than the artists themselves.

In 2001, Shawn Fanning and Sean Parker nearly killed the music industry when they introduced Napster, which allowed consumers to download music for free. Although the industry successfully put Napster out of their misery, streaming apps like Pandora and Spotify that rose in their place weren’t much better for artists. In November 2014, Swift removed her catalog from ad-supported, free music streaming platforms like Spotify. A platform that, unsurprisingly, Napster founder Sean Parker helped to build and develop into a global powerhouse.

Perhaps due to riding high on the success of 1989, Swift seems to have renewed efforts to “shake off” the ongoing feud with West. In February 2016, Swift and West were photographed together looking decidedly chummy at the Grammys, where Swift won both Album of the Year as well as Best Pop Vocal Album, making her the first woman ever to win AOTY twice. In an interview, West even implied they might collaborate together musically. In the September issue of Vanity Fair, Swift confirmed that they had developed a cordial relationship (largely at the urging of Jay-Z), but denied there was any talk of a musical collaboration. That same month, Swift even presented West with the prestigious Video Vanguard Award at the 2015 VMA’s, where the video for her single Bad Blood also won Video of the Year.

Also in 2015, Apple unveiled its new music streaming service, which included a 3-month free trial. It was quickly revealed, however, that Apple did not intend to pay artists for songs that were streamed during this time. In June of 2015, Swift published an open letter in which she criticized Apple for this move and threatened to withdraw her music from the platform. Apple responded by announcing they would pay artists during the free trial period, and Swift agreed to keep her catalog on the platform. In 2017, however, Swift’s label, Big Machine Records returned her catalog to Spotify among other free streaming platforms. A move which would later lead to one more battle between Swift and the men trying to control her catalogue and her career.

In February of 2016, however, all hell would break loose on a different front when West released his seventh studio album The Life of Pablo, which included highly controversial lyrics on the song “Famous.” Unlike Swift, who never mentions by name who certain songs are about, West left nothing to the imagination by calling Taylor Swift out by name.

“I feel like me and Taylor might still have sex/ Why? I made that b—h famous.”

In fact, in an early leaked version of the track, West actually states that he believes Swift owes him sex due to his belief that he made her famous. A subsequent video for the song featured an extremely life-like wax sculpture of a very naked Swift. As controversial as the line and the video may have been, nothing could compare to the firestorm surrounding how the lyric came to be in the first place.

At the time West released the album, he claimed that Swift herself had approved the lyric. Soon after, Swift released a statement through her publicist, stating that “Kanye did not call for approval, but to ask Taylor to release his single ‘Famous’ on her Twitter account.” In June of that year, Kim Kardashian gave an interview to GQ in which she defended her husband’s version of the events, while also claiming to have a recording of the conversation. The following month, Kardashian posted an edited version of the conversation on Snapchat in which Swift seemingly appears to have approved the first line, but not the second.

Although the recorded conversation did not actually prove Swift be a liar, once again, the public narrative was very carefully crafted against her. One in which West (and Kardashian) were once again somehow painted as heroes and Swift herself made out to be the villain. For those just now becoming aware of the decades long saga of Swift and West, it’s important to understand the complete imbalance of power that was present at that time. Although Swift was certainly famous and powerful on her own, the combined forces of West and Kardashian were at the time very similar to the combined forces today of Swift and Travis Kelce. So, to put this in context, imagine Swift and Kelce joining forces today in an attempt to destroy Ariana Grande.

What is also important to understand about this period in time is that in April of that year, Swift starred in a hilarious Apple Music commercial in which she falls off a treadmill while rapping to Drake and Future’s Jumpman. Following the commercial the track saw a 431 percent increase in sales on iTunes alone, while the #gymflow playlist she tapped into grew by 325 percent. Which is to say that throughout her career, Swift has shown a remarkable willingness and ability to increase the visibility of male artists, all while consistently being attacked by both male artists and the press.

Like many women, regardless of what Swift does, she will always be painted in a negative light in the media. In 2015, Swift dated Scottish DJ Calvin Harris. In July 2016, TMZ reported that Swift secretly wrote Harris' hit song "This is What You Came For" under the pseudonym Nils Sjoberg (Interestingly enough, a male pseudonym). Although Swift did eventually confirm the rumors, Harris claims (probably truthfully) that it was Swift that wanted to keep the collaboration a secret. TMZ implied, however, that their relationship had fallen apart due to Harris not wanting to reveal her identity as the songwriter.

What is perhaps far more accurate is that Swift was more than happy to keep it a secret as she was likely well aware by this time of the impact her success had on her relationships. Hollywood is nothing if not an enormous graveyard of marriages that mysteriously seem to fall apart when a woman’s career eclipses that of her male partner. Regardless, the story broke at almost the exact same time Kim Kardashian posted the edited recording ostensibly making Swift out to be a liar about giving West permission to include her in his lyrics. Kardashian began using a snake emoji to refer to Swift and detractors quickly followed suit. Together, the two incidents seemed to combined to spawn the hashtag #taylorswiftisover.

In reality, much of Swift’s fame is less of her own creation as much as mainstream media’s treatment of successful women. An obsession that has clearly broken a long string of lesser mortals. In other words, the media create the monsters they accuse women of being, then burn them at the stake when they break.

In 2017, British GQ wrote that Swift became "a lightning rod for accelerating cultural anxieties about race, gender and privilege." The same media absolutely obsessed with her “girl squad” of female celebrity friends including models, actresses and singers, (in fact, coining that name themselves) also chastised her for supposedly promoting some idea of feminism which included "impossibly beautiful women flaunting impossibly perfect lives." While roasting her for the short duration of her relationships, they also refuse to acknowledge how impossible it is to try and create intimacy under the blinding glare of the public spotlight.

Following Kardashian’s release of the the edited conversation between Swift and West and the Calvin Harris controversy, Swift reportedly entered a very dark phase of her life. Feeling it necessary to leave the country the same way West did nearly a decade earlier, Swift retreated to England. In part 3 of this series, I will explore Swift’s subsequent relationships over the next several years and the role the media almost assuredly played, another defining event that took place and how they all relate to her most recent album, The Tortured Poet’s Department.