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An Era-by-Era Recap of Taylor Swift’s Career

by Isabelle Zarrin


Country-turned-pop icon Taylor Swift made her music debut in the early 2000’s before earning her spot as a household name worldwide. Born December 13, 1989, in Reading, Pennsylvania, Swift quickly discovered her love for music and performing. As a result, at the age of fourteen, her family left their Christmas tree farm and headed for Nashville, Tennessee so Swift could pursue this passion.


While living in Nashville, Swift signed to the record label Big Machine Records, founded by Scott Borchetta, and owned by Scooter Braun. Swift released six studio albums under Big Machine before her life's work was stolen from her by the label. To make a long story short, Swift was denied the ability to purchase the rights to her master recordings for years, though Borchetta willingly sold the music to Braun without Swift's knowledge. Not having ownership over her masters meant that Swift would not earn royalties from her work or have a say in where her music is used. Subsequently, Swift took matters into her own hands and announced that she would be releasing re-recorded versions of her first six albums with her new label, Republic Records, to reclaim her legacy as a writer. This has arguably been the most pivotal moment in Swift's career, although it was not the first time she was faced with controversy. Throughout her time in the public eye thus far, Swift has been no stranger to criticism over her music, as well as her character. However, she has never let the scrutiny stop her from unapologetically being herself and snapping back at those that doubt her talent and genuine heart.


At the age of sixteen, Swift entered the country music scene with her debut album Taylor Swift. The self-titled record consists of fifteen tracks that describe her thoughts and feelings as a teen girl learning to navigate adolescent love and heartbreak. The album truly embodies this essence, with lovesick tracks such as “Tim McGraw,” and “Teardrops On My Guitar,” as well as resentful anthems like “Picture To Burn,” and “Should've Said No.” Acoustic guitars, banjos, fiddles, diary-entry lyrics, and a fake country twang are what make the record so wholesome and charming. Swift impressed the public with the strong songwriting abilities she possessed as only a freshman in high school, earning her a top twenty spot on the Billboard 200 in the album’s first week. The album peaked at number five after sixty-three consecutive weeks, making it the longest stay on the Billboard charts by any album released that decade. The success of the album, which also featured tracks like “A Place in this World,” “The Outside,” and “I'm Only Me When I'm With You,” showed that Swift was truly destined to be a star.


Two years after her debut, Swift released her sophomore album titled Fearless. Similar to her previous self-titled record, Fearless flawlessly encapsulates a coming-of-age theme with a country-pop flare. Swift's lyrics throughout the record detail the highs and lows of her familial, platonic, and romantic relationships. Most famously, the album contains stories of Swift's public relationship with actor and singer-songwriter Joe Jonas, on tracks such as “Forever & Always.” Fearless debuted at number one on the Billboard 200 chart, and it sold 129,000 digital copies within the first week of its release, making Swift the artist with the best online start for any country album in history. Swift was quickly shining with success, thanks to radio-friendly hits like “You Belong With Me.” However, with great success comes the inevitable presence of haters. At the 2009 MTV Video Music Awards, Swift was awarded Best Female Video for “You Belong With Me.” During Swift's acceptance speech, rapper Kanye West invited himself onstage, took the microphone from Swift, and spoke the now-infamous quote “I’ll let you finish, but Beyoncé has one of the best videos of all time.” This ill-mannered incident resulted in the shocked audience booing West off the stage. In her 2020 Netflix documentary Miss Americana, Swift reflects on the night stating that at the time, she thought the crowd was booing her, and that “...for someone who based her whole belief system on getting everyone to clap for you, the whole crowd booing is a pretty informative experience.” Swift also speaks of the incident as a “catalyst for a lot of psychological paths that [she] went down...that were not all beneficial.” The experience was nothing far from traumatic for a then only nineteen-year-old Swift. This era was not all negative, however. It was at this time that Swift embarked on her first tour, traveling the U.S. and Canada, connecting with fans on a new level, and going as far as conducting meet and greets after her shows.

It is also important to note that Fearless is the first album Swift decided to re-record following her resignation from Big Machine Records. In 2021, Fearless (Taylor's Version) was released with the original twenty songs, as well as an additional six (From The Vault) tracks that did not make the original album cut. For Swift, this was a crucial step in solidifying her place in the music industry by taking back what was hers. Fearless has many great songs, including “Hey Stephen,” “Tell Me Why,” and “Today Was A Fairytale.” Not only are the songs memorable for their clever lyrics, but they are also sonically interesting thanks to the unique production. The Fearless era was a key part of Swift's rise to fame, despite the obstacles she had to face on the way.

In 2010, Swift released her first and only entirely self-written album titled Speak Now. Continuing the theme of her previous craft, Speak Now was a country-pop record, but it varied from her other projects with its slight rock influences and electric guitars. The album won the Grammys for Best Country Solo Performance and Best Country Song for the radio hit “Mean.” In addition, the song also earned a cover performance on the popular show Glee, as well as another track from the album titled “Mine.” Throughout the record, honest lyrics give an inside look at Swift's personal life. Swift had built up a reputation for dating awful guys, as her lyrics often described them as such. A good example of this can be found in “Dear John,” a song where Swift hints at being groomed by singer-songwriter John Mayer. The two were romantically involved with one another when Swift was only nineteen and Mayer was thirty-two. The relationship was rightfully controversial, with many questioning their large age gap, however not much else is known about their time together. On the opposite end of the spectrum, Swift reflects on how she failed to be a good partner to actor Taylor Lautner in their short-lived relationship with the apology song “Back To December.” The song was different from anything Swift had written before – it was self-aware of her faults in the relationship. To this day, it is considered to be one of the few breakup songs she has written where she assures listeners the subject of the song is actually a great person, and she was the one who had messed things up. In the conversation of lyrics, it was during the Speak Now era that Swift faced criticism for a song that some called misogynistic. The song in question is titled “Better Than Revenge,” a track filled with angsty rage toward a situation in which an unnamed girl took Swift's place after the end of a relationship with an ex-boyfriend. In the song, Swift states that this girl is “...better known for the things that she does on the mattress,” leading the public to question the absence of Swift's previously claimed feminism. However, in a 2014 interview with The Guardian, Swift defended her past self, stating that she was eighteen at the time, “...the age you are when you think someone can actually take your boyfriend. Then you grow up and realize no one can take someone from you...” It is clear that Swift has since grown and no longer believes that belittling a woman for her sexuality was a mature way to handle the situation. This controversy has some fans wondering if Swift will change the offensive lyric when she eventually re-records the album, although she has not yet confirmed if such a lyric change will take place. Despite some questionable lyrics, Speak Now is a fan favorite, once again prompting Swift to tour the album and continue to have meet and greets with fans. Overall, the record was well-received and features tracks like “Enchanted,” “The Story Of Us,” and “Haunted,” which express such a wide range of emotions that deeply resonate with the listener. Speak Now symbolized a great amount of growth in Swift's writing and created a seamless path to follow for her upcoming work.


Following her pattern of releasing a record every two years, Swift released her fourth studio album, titled Red, in 2012. Filled with well-known hits such as “We Are Never Ever Getting Back Together,” and “I Knew You Were Trouble,” Red is known as Swift's breakup album, inspired by the record's bitter and heartbroken lyrics detailing her public relationship with actor Jake Gyllenhaal. The album was highly experimental, with Swift shying away from her usual country sound and diving into the pop music scene. Rolling Stone described Swift's self-discovery record as “...one of the best stories in pop.” Swift wrote of more complex relationships than she ever had before, describing constant betrayal from a partner in the emotional ballad “The Last Time,” featuring Gary Lightbody, as well as exploring the feeling of knowing you're better off without someone no matter how much you want them back in the self-reflective track “I Almost Do.” Red is arguably Swift's most versatile album to date, with such a wide range of genres packed into the project that it’s almost guaranteed there is something for everyone to enjoy. Like her previous records Fearless and Speak Now, Red was toured with sixty-six North American shows, thirteen being in sold-out stadiums. Swift was praised for the record by fans, however, she faced criticism from the public for often writing about ex-boyfriends. The Village Voice defended Swift's lyrical content by stating that she is unfairly “...discredited when plenty of other, more egregious songwriters are let off the hook..." and that “It's really easy to dismiss a blonde girl trying to play by the rules." This snapback makes it clear that Swift writing about her life experiences is nothing new, and she should not be shamed for it when others aren't.

The Red era was filled with fun, and luckily for fans, this fun was reignited in 2021 when Swift released Red (Taylor's Version) with remade recordings of the album's original twenty-one tracks and an additional nine songs (From The Vault). Swift also released the highly anticipated “All Too Well (10 Minute Version)," an extension of the beloved five-minute track, accompanied by a short film adaptation starring actors Sadie Sink and Dylan O'Brien. Red is a beautifully written project, and it contains what is often considered one of her greatest songs, “Holy Ground." The song encapsulates the familiar feeling of fondly reminiscing on sacred memories. Upbeat production by Jeff Bhasker gives the track a feel-good energy to match the positive lyrics inspired by one of Swift's past whirlwind relationships. Red is a record loved by many, prompting Swift's fan base to eagerly follow her into the coming era full of excitement for what she would do next.


Taking it back to the year she was born, Swift released her smash hit album titled 1989 in the year 2014. The record takes inspiration from upbeat 80’s synth pop thanks to her new collaborator, producer Jack Antanoff. Swift was living in New York at the time of creating the project, and this influence is highly evident in her sassy, unapologetic lyrics in songs like “Shake It Off." The album brought Swift great success, debuting with 1.28 million copies sold in the U.S. alone in just the first week of its release. Swift also was awarded Album of the Year at the Grammys, as well as embarking on her sold-out world tour. Although Swift seemed to be on top of the world, this was quickly put to an end when rapper Kanye West called, asking for permission to include some controversial lyrics about her in his upcoming song titled “Famous." The lyrics were sexually explicit and targeted Swift, but she hesitantly approved. What she did not approve of, however, were the misogynistic lyrics aimed at her that were later added in without consent. As previously explained, Swift and West do not have a friendly past, but the two had since come to a somewhat mutual respect. However, this respect was no longer present when West and his then-wife Kim Kardashian illegally recorded, edited, and released the call with Swift to make it appear as though she approved of all lyrics. This made her seem like a liar to the public when she called out West's unprovoked remarks toward her in the song. The Kardashian-West fanbase swarmed Swift's social media with hateful messages and snake emojis, while also getting #TaylorSwiftIsOverParty trending on Twitter. In her 2020 documentary Miss Americana, Swift reflects on this time in her life stating that “When people decided [she] was wicked and evil and conniving and not a good person" she “...couldn't really bounce back from [it]."

The overwhelming pressure from the world pushed Swift to exit the public eye. Regardless of the controversy, 1989 remains one of the best pop albums of all time, and the deluxe version of the record includes Swift classics like “New Romantics." The track delves into the idea that many young adults approach love in an unserious, whimsical way and Swift embraces herself as one of those people. Overall, the album will forever remain iconic for its pure pop manifestation.



Breaking her pattern of releasing an album every two years, reputation was released by Swift in 2017 after a year of radio silence from the pop star. Swift's social media presence was gone, and as she states in Miss Americana, she “...just wanted to disappear," and “...nobody physically saw [her] for a year," which was what “...[she] thought they wanted." For fans, it was truly heartbreaking to hear how Swift felt in her year of isolation from the world. Luckily, when she made her comeback, the record was highly anticipated for its dark and revengeful, yet simultaneously optimistic feel. Sonically, reputation kept pop elements, while taking inspiration from the hip-hop genre. Accompanied by impressive vocals, lyrics show Swift embracing the villain she was painted to be in fan favorites such as “I Did Something Bad," and “Don't Blame Me." Snake symbolism in clothing and stage design on her record-breaking stadium tour, which was documented for a Netflix concert movie, is reminiscent of the comments she received a year prior after the infamous scandal with the Kardashian-West family. Many consider this to be Swift's revenge album, as it contains stabs at those who have wronged her in the past. However, there are positive tracks portraying her blossoming romantic relationship with actor Joe Alwyn, such as “Delicate." In the song, Swift states that her “...reputation has never been worse so [he] must like [her] for [her]." Swift and Alwyn's relationship has remained strong ever since, keeping their amorous entanglement private from the world. One thing Swift did not shy away from, however, was expressing her political viewpoints to the world. With the upcoming midterm elections in 2018, Swift wrote on Instagram: “In the past I've been reluctant to publicly voice my political opinions, but due to several events in my life and in the world in the past two years, I feel very differently about that now...I believe in the fight for LGBTQ rights…that the systemic racism we still see in this country towards people of color is terrifying, sickening, and prevalent...I cannot vote for someone who will not be willing to fight for dignity for ALL Americans, no matter their skin color, gender, or who they love." This was an important statement for many of Swift's fans to hear, especially those who belong to minority groups as Swift had not been vocal about her political stance prior.

Swift expressed a bold, unapologetic personality in this era, and this translates into the contents of reputation making it a genuinely mind-blowing record. “Ready For It…,” one of her strongest album opening tracks, pairs dark production with lyrics that Swift described at a private concert as “...basically, finding your partner in crime, and it’s like ‘Oh my god we’re the same, we’re the same, oh my god! Let’s rob banks together, this is great!’" To many, this record is representative of personal growth, and it did an excellent job of clearing Swift's image after previous setbacks.


Following the iconic 2017 record reputation, Swift released her 2019 album titled Lover. The project was symbolic of happiness, freedom, and letting go of the past. It was the first record Swift released under her new label Republic Records, making it the first piece of work she owned after having her masters stolen from her. Lover was the polar opposite of Swift's previous record, incorporating bright colors with pure pop lyrics and production in songs like “ME!" and “Cruel Summer." In a 2019 interview with Rolling Stone, Swift describes Lover as “...a return to the fundamental songwriting pillars…" and “...really honest…not [her] playing a character." Swift says that Lover contains “...very personal admissions…" making it her most intimate record yet. In a 2019 interview with Elle, Swift says that Lover “...celebrates love in all its complexity. Not just flowers and sunshine but the patchwork emotions that go into any love you feel." In January 2020, Swift released her long-awaited documentary, Miss Americana. The film follows Swift through her reputation tour up to the release of Lover as she opens up about battling an eating disorder, giving viewers a glimpse at her relationship with Alwyn, and even deeply personal conversations about her mother's cancer diagnosis. During this time, Swift was also set to begin her sixth tour, which she called Lover Fest. The tour was set to begin in April 2020, however, due to COVID-19, the tour was postponed before unfortunately being canceled. As a result, Swift took to social media to state, “I'll see you on stage as soon as I can but right now what's important is committing to this quarantine, for the sake of all of us." The Lover era was short-lived, but it blessed fans with feel-good songs that will last a lifetime, including “I Think He Knows," and “Death By A Thousand Cuts," both possessing upbeat production and personal lyrics detailing both the good and bad sides of Swift's relationships. Lover allowed Swift to express sides of herself she hadn't before, and she continued to do so after the release of the record.


In July 2020, Swift shocked fans by releasing her surprise album folklore. The record came only eleven months after Lover as a result of Swift having an abundance of time to write during the peak of the pandemic. Collaborators Jack Antanoff and Aaron Dessner brought Swift's make-believe world to life with indie-folk-inspired production and vivid imagery in lyrics. Swift explored a type of writing she hadn't before, telling the stories of characters she made up while in isolation. She created a fictional love triangle between the characters James, August, and Betty in the songs “cardigan," “august," and “betty." In a 2020 Youtube Q&A, Swift says that the songs “...explore a love triangle from all three people’s perspectives at different times in their lives.” The song trilogy is captivating as a listener and allowed Swift to create work that was not autobiographical. The folklore album was a massive success, earning six Grammy nominations, and winning the award for Album of the Year. The record also got recognition from Disney+, with a music documentary titled Folklore: The Long Pond Studio Sessions, directed and produced by Swift herself. It acts as somewhat of a concert movie, with Swift performing the album live at Long Pond Studios and giving background information on the songs.

Impressively, six months after the release of folklore, Swift surprise-released her ninth studio album, evermore. The album acts as a continuation of the stories told in her previous record, and Swift describes them as sister albums. Keeping the same indie-folk elements as folklore, the record takes a turn, diving into heavier topics such as grief and infidelity. Returning collaborators Antanoff and Dessner help Swift go back to her roots adding a touch of country inspiration in tracks like “no body, no crime" featuring girl group HAIM, and “cowboy like me." Due to the global pandemic, Swift could not tour to support either of these albums, however, fans still loved them both. They are considered Swift's best lyrical work in her career thus far, withholding powerful songs like “mirrorball" from folklore, and evermore bonus track “right where you left me." The songs are some of the best in her discography, with “mirrorball" being a magical take on the need to be a people pleaser, and “right where you left me" expressing the difficulty to move on at the end of a relationship.

Two years after folklore and evermore, Swift announced her tenth studio album Midnights. Swift announced the record at the 2022 MTV Video Music Awards, saying “...I thought it might be a fun moment to tell you that my brand-new album comes out Oct. 21. And I will tell you more at midnight.” As she promised, more information on the album including the title was announced across all social media platforms at midnight. Swift began teasing the tracklist on TikTok in a segment uploaded every other day which she called “Midnights Mayhem With Me.” With the help of a bingo cage, Swift selected ping-pong balls numbered one through thirteen and revealed the name of the track number she pulled from the cage. When the album was released, fans were exposed to beginning themes of self-doubt, insecurity, and anxiety while ending on a hopeful and confident note. Just three hours after Midnights was released, Swift gifted fans with seven additional tracks on the deluxe album Midnights (3am Edition.) Ten songs from the project made it to the top ten spots on the Billboard Hot 100 in its first week, the most for any album in history. A Target-exclusive CD was also released, which contains remixes of tracks “Sweet Nothing” and “You're On Your Own, Kid,” as well as the bonus track “Hits Different.” The Midnights era was as short as the Lover era, but even in a small amount of time, it had a heavy influence on the trajectory of Swift's future.


Swift's fan base has been constantly growing since the start of her career, making the demand for her concert tickets extremely high. Following Midnights, she announced her highly anticipated U.S. leg of the Eras Tour, a celebration of all of her previous albums. Ticketing partners Ticketmaster and Live Nation Entertainment conducted a Verified Fan presale for the fifty-two shows. The presale was for those who signed up by email and were given early ticket access at random selection with a personalized entry code. However, the companies had sent out more presale codes than they were supposed to, leading the site to crash and leaving fourteen million fans in a frozen queue for multiple hours. When tickets were finally accessible, they sold out in minutes, leaving those who didn't get tickets devastated. The buying process was nearly impossible, especially when Ticketmaster announced that per Swift's request, a general public sale would not be occurring. However, in order to get tickets to fans in a more effective, less stressful way, Swift called for Ticketmaster to send a small selection of those who were unable to secure tickets via presale code a ticket request form. Fans who received this email were prompted to select the price range they would be willing to pay for up to two tickets. Seats could not be selected by the fans themselves, they were picked by the company based on availability and the chosen pricing point. International tour dates have not yet been announced, so those who live outside of the U.S. as well as those who unfortunately could not get tickets have been watching the start of the Eras Tour from home via social media. The tour has a forty-four-song setlist, with two surprise songs exclusive to each show. Swift will be performing in sold-out stadiums for three consecutive hours and undergoing over ten outfit changes to symbolize each era.


Throughout her seventeen-year-long career, Swift has made a name for herself as a pop legend, a brilliant lyricist, and most importantly, an incredible person. Overcoming tough obstacles time and time again, she has displayed a great sense of resilience and passion. Beginning as a sixteen-year-old country singer with nothing but an acoustic guitar and a dream, Swift has blossomed into the thirty-three-year-old superstar known worldwide for her undeniable talent. She has grown a massive fanbase of people who idolize her thanks to her charm and power to captivate audiences with her words. Ten studio albums, six headlining tours, and a love for her craft have led her to become the icon she is today. There is no telling what Swift will do next, but it is without a doubt she has millions of supporters cheering her on in all of her future successes to come.


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