25. Begin Again
Featured on Red, Swift’s fourth studio album, “Begin Again” tells an incredibly bittersweet tale. The narrator of this song sings about how she became accustomed to getting disregarded by her ex. He refused to laugh at her jokes, to engage in things that interested her, and to overall care for her how he should have. However, the new man the narrator has met treats her in an opposite fashion. He throws his head back laughing at her jokes, meets her with common interests, and makes her feel wanted. Swift does a beautiful job portraying how a toxic relationship can alter one’s way of thinking. People like the song’s narrator begin to believe that they are truly uninteresting, or unworthy of love due to the opinion of the person they cared for. Yet, Swift reminds listeners that there’s hope to meet someone who will remind you of your worth, and let you begin again with new hope for the future.
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24. Last Kiss
“Last Kiss” is yet another emotionally devastating track off of Speak Now. On this song, Swift captures the feelings of grief that come with losing a relationship that you weren’t ready to have end. Filled with a sense of mourning and sorrow, Swift sings about how she never planned on the song’s subject “changing [his] mind” about her, and how she doesn’t know how she can be something he misses. You can hear the self doubt building in her voice as the song moves forward, questions of why she wasn’t good enough for someone she loved so much building in her head. Swift masterfully displays the range of grief anyone feels when they lose someone and hold no control over the situation, and she creates instrumentals that match her crushed spirit. While I wouldn’t recommend turning this song on when you want to be in a good mood, it deserves credit for doing such an effective job at representing real, raw heartbreak.
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23. Haunted
“Haunted” takes on a very different sound from the rest of the Speak Now album. While this record is rooted in a fantasy-like feeling, exploring the wistful emotions that surround falling in love, “Haunted” explores what happens when that kind of romance ends abruptly. Featuring heavy drums and harsh strings, the production of this song makes listeners feel like they’re running through a dark forest of their own emotions, desperate to get away from the heartbreak threatening to destroy them. Swift sings with a palpable sense of desperation, as if she’s truly begging the subject of her song not to leave her. Yet, her voice carries an undertone of defeat, like she’s accepted that the creeping heartbreak she feels is inevitable. She portrays the haunting inevitability of heartbreak with incredible conviction, and that’s what makes the song such a triumph in Swift’s discography.
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22. Innocent
Making its debut on her third studio album, Innocent is a unique song for Swift. This song is not about herself or any ill-fated relationships she’s been in. Rather, it’s about Kanye West. Following the infamous incident at the 2009 VMAs — where West stormed the stage after Swift’s win for Best Music Video, stole the microphone from her, and subsequently announced that he felt Beyoncé should’ve won — most expected Swift to react with outrage.
Instead, she wrote “Innocent” — a slow, melodic song asking people to remember that while what West did was wrong, he was once a young boy chasing fireflies and playing on a school yard. This song is imbued with forgiveness for both West and his inner child, reminding listeners that people are not defined by their bad moments, and should instead be judged by the sum of their parts. While their relationship did not age well, this song has and it stands as a shining example of what real forgiveness and kindness can look like.
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21. Fearless
If any song perfectly sums up Taylor Swift’s music, it’s the title track off her second studio album. “Fearless” encapsulates the courage and recklessness that falling deeply in love for the first time requires. Its sound captures the optimism that people carry in their first relationships — the excitement, the nerves, the desperation. “Fearless” is a song written by a girl who has yet to learn to be careful with her heart, and is filled with a youthful, innocent energy that can’t be faked. As Swift’s discography — and list of lovers — has grown through the years, she’s made sure to never lose the initial enthusiasm for love that “Fearless” was imbued with. For setting the tone for her career, it is one of her best songs.
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20. Nothing New (feat. Phoebe Bridgers)
“Nothing New” is arguably one of the most soul crushing songs on Red (Taylor’s Version). As Swift’s music has grown with her life experience, she’s begun addressing more than just love and breakups in her music. In more recent works, Swift has examined the complicated and scary feelings that come with aging in the industry, and “Nothing New” addresses exactly that — while also making it relatable for audiences who will never experience the instability of the entertainment industry.
Together, Swift and Bridgers sing a soft, haunting song about what happens as you grow, going from knowing “everything at eighteen, but nothing at twenty-two.” You don’t need to be a celebrity to recognize the sense of hopelessness this song captures, that comes from not knowing what to do with your life — feeling like you’re both too young to make a permanent decision, but getting too old to be found endearing by those who ask what your life plan is. Both lyrically and tonally beautiful, “Nothing New” is the perfect song to play when you want to feel less alone in your life struggles.
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19. cardigan
When Swift set out to write her 2020 album folklore, one thing she knew for certain was that it wouldn’t contain songs solely based on her life experience. She took this record as a chance to explore fictional storytelling through song. “cardigan” — the second track on the album — is the first song in a trilogy off folklore that tells the story of a love triangle between the characters Betty, James, and Augustine. “cardigan” is told through the perspective of Betty, a teen girl experiencing her first real love, and her first real heartbreak. This is a song that makes the little details count, like the distinct sound of chimes in the background of the song to indicate the mystical feeling of first love, to the metaphors in the lyrics that take time to dissect. “cardigan” is a triumph, and a true testament to Swift’s songwriting abilities explored in this new avenue of storytelling.
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18. Blank Space
“Blank Space” took the world by storm following its release in 2014. One of the lead singles off Swift’s album 1989, it spent seven weeks on Billboard’s Hot 100, earned three Grammy nominations, and was revered as decade-defining by Billboard. Accolades aside, this song earned such favorable attention by having clever, self-referential lyrics, and satirizing the stereotypical perception of “crazy” women in the media. Swift embraces the image of her created by tabloids in this song, singing about getting “drunk on jealousy” and being a “nightmare dressed like a daydream.”
Although she is mocking the public perception of her personal dating life, this song still speaks for the harsh and unrelenting criticism that women have faced since — well, forever. Swift proves with this song that there is power in reclaiming the cruel things you are called by others, and gifted the world a pop hit in the meantime.
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17. All You Had to Do Was Stay
When Swift announced in 2014 that she’d be shifting from the country genre to pop, there was unending concern from critics, fans, and her own personal team as to how the jump would impact her music. The assumption was immediately made that by making a pop album, her lyricism and sound would suffer — overwhelmed by the synthetic sound that so many pop stars take on. However, Swift proved them wrong and “All You Had to Do Was Stay” is a prime example of that. While the sound of this song is heavily pop, the lyrics — when listened to closely — are heartbreaking. The true power of Taylor Swift lay in songs like this. One second you’re dancing to an upbeat pop hit, and the next you’re crushed by the weight of the words she’s singing. This song proves that no matter what genre Swift moves to, her magic power will always be in her ability to craft a story and tell it through lyrics.
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16. You Belong With Me
“You Belong With Me” is arguably one of the most popular and recognizable songs Swift has ever released. This song captures the true angst of teenage pining, but portrays it in such an upbeat manner that listeners can forget the words they’re singing are sad. “You Belong With Me” tells the tale of its narrator, yearning for the guy who sees her as just a friend to leave his girlfriend for her. This track perfectly captures how it feels to be the underdog in high school — watching from the sidelines as more popular people around you get the love and attention you crave. Not to mention, its music video is iconic. From the Love, Actually style form of communication between Swift and her crush via notes written on large notebooks, to Swift playing her own antagonist in a wig, this music video left an impact on an entire generation of young girls with access to YouTube in 2009.
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15. ivy
Featured on evermore, “ivy” follows Swift’s latest trend of writing songs about fictional scenarios. Although it was not made a single, it’s a fan favorite off the album, and is vastly appreciated by evermore fans across the world. Listening to “ivy” is akin to watching Pride and Prejudice: it transports you to somewhere magical, somewhere filled with romance and castles and forbidden love. This song tells the story of its narrator trapped in a loveless marriage, left pining for the one she truly loves.
Swift displays her masterful command over metaphors in this song, as she likens the narrator’s feelings for her forbidden lover to the ivy that spreads over forgotten stone — ever growing and unstoppable. Swift’s lyrics and the sound of the song work in tandem to transport listeners to a faraway land, where love exists even for those who looked in the wrong place first.
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14. You’re On Your Own, Kid
“You’re On Your Own, Kid” is another track off of Midnights. This song shows off Swift’s ability to tell a long story in a short amount of time, as it follows its narrator from her childhood to adulthood — pointing out the lessons she learns along the way. As she begins to experience disappointments, our narrator realizes she’s on her own in life, and the idea is daunting. However, as she moves through her life and begins to work through the sacrifices she must make to achieve her dreams, she realizes there is something liberating in only having one’s own self to worry about. This song is about finding freedom in independence, and treating yourself like the main character of your own story. While initially soul crushing, the tone of the song turns around and becomes hopeful, and ultimately reassures every overwhelmed 20-something in the world that they’ll be alright.
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13. Enchanted
Did you know that Swift’s third album, Speak Now, was originally titled “Enchanted,” after this track? Swift felt the title — and the song itself — best conveyed the tone of the album: wistful, magical, and full of yearning. Although her label disagreed and moved forward with the title Speak Now, this track still best encapsulates what Swift wanted people to feel when listening to her music. With instrumentals that build and build, leaving listeners with heightening anticipation, they feel every emotion with Swift — hoping that whoever is getting sung to by Swift really isn’t in love with someone else. This song is an auditory representation of when you can’t help but get butterflies in your stomach when someone looks your way; when you fall hard and fast for someone you barely know. This song is what falling in love sounds like, and Swift’s ability to bring it to life is just a part of her unending talent.
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12. The Way I Loved You
“The Way I Loved You” is a true Taylor Swift classic. It’s the type of song that you sing at two in the morning, windows rolled down, speeding down a road with your friends. Every line is scream-out-loud capable, making you want to get up and dance in the meantime. This song is the perfect encapsulation of what the true magic of Taylor Swift is. Even as she sings of love and loss, of breakups and pain, she finds a way to make those harsh emotions palatable for those who are experiencing them. “The Way I Loved You” is a perfect representation of the playful manner her songs often take, even amidst harsh and depressing realities.
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11. Maroon
“Maroon” is the second track off Swift’s latest release, Midnights. This song conveys the ups and downs of a relationship that’s far too tumultuous to last in the long-term. The genius of this song lay in its chorus. Sung in a rushed manner, she moves through memories of her past relationship as if they are flooding her brain in waves of red. The synthy, dark sound of the song adds to its tone — making it seem like Swift is lying awake at night, haunted by the good parts of her relationship, but too scared of reliving the bad parts to consider revisiting it. While red typically represents love, it also represents passion — and Swift is sure to show how too much passion can become explosive when not handled correctly.
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10. Wildest Dreams
Is it too on the nose to say that “Wildest Dreams” is one of Swift’s dreamiest tracks? Well, even if it is, I won’t take it back, because it’s true. “Wildest Dreams” tells the story of a love affair doomed to end. Both the narrator and her lover know their relationship is going to explode. But, for the time being, they choose to live in the moment and adore each other. The layering of vocals and use of string instruments makes listeners feel like they’re in a daydream, reminiscing about a relationship they never were a part of. On top of that, this song displays the strength of Swift’s vocals, as she belts the final chorus and displays a part of her range that doesn’t always come out.
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9. mirrorball
mirrorball, another track on folklore, has made such an impact on those who listen to it that many Swift fans across the world now sport tattoos of disco balls in honor of this song. If permanent art on one’s body isn’t the ultimate proof of the song’s effect on its listeners, I don’t know what is. mirrorball reflects on an experience many — especially women — feel they have in society. Swift writes about how people will become human mirror balls, doing their best to reflect the personalities of those around them back to whoever they are trying to impress.
The mirror balls of the world just want others to laugh with them and give them the positive attention they crave, and they have no problem shining all their light on others to reach that goal. To be a mirror ball is to be made of a million fragmented pieces — making them inherently broken things spinning out of control. This song expresses the deep yearning so many have to just be liked in a beautiful way, and has resonated deeply with audiences who hear it.
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8. Call it What You Want
While most of reputation’s tracks are heavy on synth and carry a true pop feel, “Call it What You Want” strays from that pattern. Rather than sounding heavily produced, it’s stripped down — relying mostly on Swift’s voice and a simple beat to tell its story. In this simple but beautiful song, Swift sings about falling in love with her current partner and boyfriend of six years, Joe Alwyn. This song is deeply personal for Swift, as it details her fall from fame in 2016-17, and how in the time she was gone from the public eye, she fell in love with one of the few people who did not leave her amongst her public drama. This song is about the depth of true love, and how all that matters is for one person to understand you, even if the rest of the world doesn’t. This song sounds like what falling in love with the right person feels like: simple and relieving.
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7. Getaway Car
Not only is “Getaway Car” one of Swift’s best songs, it also contains one of her best bridges to date. Written by Swift and her longtime producer/friend Jack Antonoff, this reputation hit tells the story of its narrator desperate to get out of the lackluster relationship she’s stuck in. Instead of using literal language, however, she equates escaping the relationship to escaping a crime scene. This song is genius, as it encapsulates how heart-racing and dramatic a breakup can be. Further, this song addresses an emotion that is seldom expressed in Swift’s breakup songs: freedom. Rather than getting broken up with, our narrator is hellbent on ending things with the partner she’s singing about. You can feel the joy in her voice and in the tense build up of the bridge when she finally frees herself from the relationship. It’s a fresh perspective for Swift, and is a standout on reputation for that reason.
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6. Style
Rumored to be about Harry Styles, this track off of 1989 is one of Swift’s best-known singles and radio hits. “Style” tells the story of two people who are infatuated with each other, but are too busy with their lives to commit to a real relationship. Instead, they sneak off together when they can — reveling in each other’s presence for as long as their adventure lasts. This track is a true pop song, made of a fun and upbeat sound and lyrics to match. Swift sings as though she’s excited by the subject of the song, and as if the mere thought of them is enough to send shivers down her spine. The fun of this song easily translates to whoever listens, making it an all-time favorite for many.
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5. my tears ricochet
“my tears ricochet” is the fifth song off Swift’s album folklore, and it certainly does a good job at maintaining her history of writing devastating track fives. This song is about her soured relationship with former manager Scooter Braun, and the betrayal she felt at his purchase of her old masters. However, the song is not hyper-specific, and instead expresses the crushing weight of feeling betrayed by someone you once thought you could trust with your life. The sound of the song itself is haunting, and its lyrics utilize lots of imagery surrounding death. The death she talks about in this song is metaphoric — she knows she is dead to him and vice versa, yet they can’t help but haunt each other. The lyrics and sound work together to capture the feelings that emanate from feeling you can never return home, whether that home is a person or a place. It’s one of the most lyrically masterful works on folklore, and in her entire discography.
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4. Dear John
As Swift’s discography has developed over time, her fans and critics alike have come to note a consistent pattern throughout all her albums: her track fives are emotionally devastating. “Dear John” stays in line with that precedent, as it’s the fifth track on her album Speak Now. The track does a soul crushing job at portraying the tumultuous relationship she was in with John Mayer. This song stands out for many reasons, one of them being how unlike the rest of her breakup songs it is.
Rather than being an upbeat radio hit, it’s a slow ballad — taking its time to describe the painful mind games a 19-year-old girl lives through while dating a 32-year-old man. This song is known for the vulnerability Swift is willing to put in it, as it’s impossible to ignore the devastation in her voice as she relives her pain. There is no pining in this song, no wishing for a second chance. Instead, this song sounds like a girl begging for the world to hear her regrets, to understand that this relationship was a mistake she’ll never fully heal from.
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3. Clean
“Clean” is the closing track on Swift’s fifth studio album, 1989. Rather than just being a love song or a breakup song, this song is instead about releasing what you’ve already lost. “Clean” highlights the idea that people can form an addiction to each other. Like any other addiction, once you are reliant on something — or someone — else for happiness, things turn toxic quickly. Swift equates the stage of no-contact with an ex to being sober, and explains that no matter how long it’s been, the cravings still come back. This song is chalk-full of metaphorical language that helps her get across a profound message, and addresses a breakup stage that is seldom highlighted in the media. Her lyricism coupled with the soft, freeing sound of the song makes it one of her best to date.
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2. Would’ve Could’ve, Should’ve
“Would’ve Could’ve, Should’ve” is the penultimate track on Swift’s latest release, Midnights (3am edition). Like most of her hardest hitting songs, this track explores the regret that she feels for entering a relationship at a young age that only left her traumatized and jaded. While sounding upbeat and catchy, the lyrics of this track strongly juxtapose its tone, as they explore the grief she carries for her teenage self. This song is also unique because it’s written with perspective — rather than her writing this fresh on the heels of an emotional event, she is writing this with over a decade of hindsight, making this song carry much more weight.
Ultimately, what makes this song one of her best is the way she artfully navigates complex themes like grief and loss of innocence while still prioritizing the production and sound of the song. “Would’ve, Could’ve, Should’ve” is a four-minute and twenty-one second amalgamation of everything Swift has learned as a songwriter and producer over the years, and is an example of her perfecting her craft.
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1. All Too Well
Since its debut in 2012, “All Too Well” has been regarded as one of Swift’s best songs, and for good reason. This song carries a searing hot intensity to it, but not due to the production or sound. Rather, it’s through the song’s lyrics and the way Swift sings them that listeners feel the weight of her heartbreak on their own shoulders. Starting off soft and slow, she regales the good times of her relationship — the soft moments that made her fall so deeply in love with the man she’s singing to. However, the rose colored glasses disappear by the bridge of the song, and what was once soft becomes harsh and full of malice. This song artfully plays out the journey from love to resentment that many face when their relationship ends, even when they remember the good parts all too well.
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