Best Taylor Swift Songs Of All-Time: Top 5 Tunes Most Beloved By Music Experts (And Swifties Too)

With the new release of Midnights, we at Study Finds decided to search for the top five best Taylor Swift songs, at least according to music experts. For her fans, her career has truly been a “love story.” From country to full-blown pop to indie-style ballads, there’s one thing that’s the same. Experts continually remark about her lyrics’ imagery and storytelling. This allows her fans, aka Swifties, to make connections to her songs. But first, we have to tell you …

Superstar Taylor Swift is so beloved, she’s even found a new species to call her own. One that’s one inch tall and has dozens of legs! Swifties at Virginia Tech have named a new species of millipede in the singer’s honor. Why? They credit her as helping them get through grad school. Experiments have demonstrated that listening to music can reduce anxiety, perhaps even more effectively than some anti-anxiety medications. 

And we all know Taylor’s affection for writing love songs, and breakup songs, too. Interestingly, ​​your favorite songs and musicians provide a sneak peek into your attachment style and typical relationship behaviors. Researchers from the University of Toronto report that individual attachment styles often correspond with the lyrics of one’s favorite songs. Meaning: People tend to turn to music that describes how they’re feeling about their relationships. And Taylor loves to sing about love. There are even lists entirely dedicated to her best songs for weddings

But overall, below are five of the best Taylor Swift songs, ranked meticulously by 13 brave experts. Our list is comprised of the hits that appeared most frequently Hopefully you can tear yourself away from listening to Midnights exclusively to revisit the best of the best from Taylor. With more than 225 songs under her “bejeweled” belt, you could very well have your own top five. If you do, make sure to drop us a comment with your list of favorites! 

The List: Top 5 Taylor Swift Songs, According To Experts 

1. ‘All Too Well’

The 10-minute, 13-second version of ‘All Too Well’ broke records as the longest song to ever top the Hot 100 chart.

Exclaim loves both the 5-minute song and the 10-minute song accompanied by a short film: “When Swift finally released the legendary 10-minute version of ‘All Too Well,’ it was a fun piece of fan service, but the main takeaway was that the original version was already absolutely perfect. Swift gives just enough information to place the listener inside of a breakup story that’s as vivid as a movie. The 10-minute version revealed the bitterness behind this breakup song, but the original five-minute edit omits these details, leaving a song that’s more wistfully nostalgic in tone.” 

BuzzFeed buzzes about this song: “It’s revered among critics, fans, and haters for a reason. What makes this version worthy of the No. 1 spot is the experience of listening to it. At first, ‘All Too Well’ was a song Taylor would sing on tour, holding back tears, struggling to play without getting emotional. Then, she performed it on the Grammys after realizing how powerful and universal it had become to fans and listeners. And now, we finally have the 10-minute version of the song and a short film. ‘All Too Well’ seems to have taken on a life of its own — bigger, longer, and better.” 

“So many Taylor Swift fans consider this to be her best song. They’re right. First, the sound — from the soft intro and the gentle chord that concludes it, to the subtle lack of resolution in the ending, and everything in between, every instrument and note works purposefully yet carefully to create emotion. I so much enjoy every Taylor song, but hearing this one is like moving up to another level, like entering another dimension,” Andrew M. Ledbetter writes.

2. ‘You Belong With Me’

Variety is happy without variety and just listening to this song, writing, “It’s as eternally teenaged as anything Swift ever wrote, but that’s no reason to have to grow out of it. Adult life is full of nothing if not many equivalents to high-school friend-zoning. Who among us ever stops wishing we’d be seen for our true selves by the guy who can’t take his eyes off the cheer captain, whether for us that’s the boss, peers, a distracted spouse or a seemingly indifferent deity? It is all of human yearning and striving packed into a song about remembering to take your specs off so the kid next door realizes you’re a cutie.” 

Vulture goes for this song as a top tune: “Swift had written great songs drawn from life before, but here she gave us a story of high school at its most archetypal: A sensitive underdog facing off with some prissy hot chick, in a battle to see which one of them really got a cute boy’s jokes. The line about short skirts and T-shirts will likely be mentioned in Swift’s obituary one day.”

According to Entertainment Weekly, “Swift’s sophomore effort put her solidly on the world music map and ‘You Belong With Me’ is eerily prescient for these times, what with Swift’s narrator’s refusal to don short skirts and high heels just to woo her crush. But really, this song deserves the nod.” 

3. ‘Shake It Off’

Billboard proves this is a popular pick, writing, “Swift’s devil-may-care anthem found her unabashedly looking for pop dominance, and she found it: The single debuted at No. 1 on the Hot 100 and posted four weeks at the top. Plus, its nearly six-month stay in the top 10 alone plays a major role in its status as Swift’s biggest charting single in a career with a multitude of milestones.” 

“It’s an upbeat track that encourages listeners to let go of small problems. In an interview with iHeart Radio, Taylor explained the story behind this song: ‘Shake it Off’ is a song that I wrote about having to deal with on an everyday basis … Just kind of how human beings treat each other.’ The song has received numerous accolades, including Favorite Song at the 2015 People’s Choice Awards and three Grammy nominations at the 2015 Grammy Awards,” XW reports. 

Wall Street Journal says it blows away other songs:“‘Shake It Off,’ with its upbeat tempo, earworm of a chorus and haters-be-damned message, blew away the competition in our poll, ranking as the favorite of Ms. Swift’s songs across geography and generations.” 

4. ‘Anti-Hero’

Holler says this is even one of Taylor’s favorite songs: “The lead single off Midnights proved she hadn’t lost any of her knack for writing out-and-out pop bangers. It’s a darkly comic late night confessional which Taylor has described as one of her favourite songs she’s ever written. She said of the song, ‘We all hate things about ourselves, and it’s all of those aspects of the things we dislike and like about ourselves that we have to come to terms with if we’re going to be this person. So, yeah, I like ‘Anti-Hero’ a lot because I think it’s really honest.’” 

Taylor Swift's album "Midnights" for sale at Target.
Taylor Swift’s album “Midnights” for sale at Target. (Photo by melissamn on Shutterstock)

“‘Anti-Hero’ is the evolution of her past work: from the synth-pop sheen of 1989, to the self-effacing streak of reputation and the intricate lyricism of Folklore and Evermore. The results are a densely-packed, infectious earworm and self-aware anthem,” uDiscover Music writes.

5. Mirrorball

Rolling Stone calls Taylor the queen of the ball: “Taylor shines like the disco ball gazing down on the dance floor, wondering why everybody else looks so confident and imagining how that feels. A seething ballad about a loner feeling a little too loud and a little too bright, afraid everyone’s staring at her flaws yet feeling invisible anyway. Queen of Concept.” 

SHEESH says this song is a masterpiece: “Lastly, we have the masterpiece that came out of the pandemic, Folklore. This Grammy-winning album allowed us all to escape in 2020. My favorite song from this album has been ‘Mirrorball,’ which discusses being broken and still wanting to appear perfect for someone. The song reminds me of coming-of-age movies with both the instrumental and lyrics. Swift discusses looking good to impress someone, yet feeling broken like a mirror when becoming a mirrorball. The harmonies in the song are ethereal and fit perfectly with the rest of the album.” 

What’s your favorite song by Taylor Swift? We can’t wait to read about it in the comments!

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