From her beginnings as a country artist to her reign as a global pop star, Taylor Swift has become one of the defining artists of this century — and that’s in large part thanks to her masterful song craft. Each era of the singer-songwriter’s career has included intricate, instantly memorable musical moments that it’s difficult to narrow down the best of the best to just 15. Yet these songs represent Taylor at the top of her game, whether it be through an extended heartbreak anthem or hilarious declaration of independence.
Here are Billboard’s picks for the 15 best Taylor Swift songs, from her self-titled debut through 1989.
15. Taylor Swift, «New Romantics»
A bonus track off 1989 that out-popped the bubblegum pizzazz of most of the standard track list, “New Romantics” finds Swift gliding alongside gooey ’80s synths before pogoing on the chorus with a slew of declarative statements. “Heartbreak is the national anthem — we sing it proudly,” she states, making “New Romantics” a spiritual cousin to the “miserable and magical” time she had on “22.”
14. Taylor Swift, «Fearless»
A song like the Fearless title track demonstrated why, even as a teenager, Swift’s songwriting was miles ahead of her country contemporaries. The lyrics include several Swiftian hallmarks — dancing with a romantic partner in the parking lot becomes dancing with a romantic partner “in a storm in my best dress”! — but that opening line, “There’s something ‘bout the way/ The street looks when it’s just rained/ There’s a glow off the pavement,” effortlessly creates a sense of whimsy and romance that not many artists can pull off.
13. Taylor Swift, «Mine»
The lead single from Speak Now, Swift’s follow-up to the Grammy-winning Fearless, is more muted than its predecessor’s “You Belong With Me”and “Love Story,” and understandably so: It’s a song about not just finding love but maintaining it when the meet-cute has drifted into the past. When that final chorus hits and reaffirms the caring at the heart of this Taylor Swift song, though, it’s one of her most moving moments to date.
12. Taylor Swift, «Tim McGraw»
Taylor Swift sure has come a long way from the first track on her first album, huh? Although “Tim McGraw” sounds nothing like her pop stylings, the charming debut features the same type of vocal resonance and clever wordplay that have become calling cards for Swift. Plus, the fact that she pulled off the line “When you think Tim McGraw/ I hope you think of me,” and then proceeded to become even bigger than Tim McGraw, is something to marvel at.
11. Taylor Swift feat. The Civil Wars, «Safe and Sound»
The bad news is that one of the very best Taylor Swift songs, the dark, devastated “Safe and Sound,” is not featured on any Taylor Swift album. The good news is that we live in a playlist-friendly culture, and that this collaboration with The Civil Wars for the first Hunger Games soundtrack can be included in any mournful collection of your choosing. A song about protection amidst terror, “Safe and Sound” features Swift’s voice at its most shattered, her best efforts pummeled by the marching drums outside her door.
10. Taylor Swift, «Our Song»
What if Swift had resisted the allure of pop music and committed to a lifetime of fiddle-filled country jams? We’ll never know the answer, but “Our Song” is a gloriously twangy testament to what Taylor once was, before her lyrical ability to find music in everyday life was translated to a different genre. Here, the bubbly words give way to the lush arrangement, which encapsulates the exuberance of first experiencing the world with a romantic partner.
9. Taylor Swift, «We Are Never Ever Getting Back Together»
Years after its release, “We Are Never Ever Getting Back Together” remains bitingly funny, an eye-roll of a pop song about a boy who just doesn’t get it through his thick skull that it’s time to move on. Swift deftly balanced sarcasm with the sincerity of the hook and nails one of her first pronounced attempts at mainstream pop (which became her first single to hit No. 1 on the Billboard Hot 100 chart).
8. Taylor Swift, «Teardrops on My Guitar»
Poor Drew: The object of Taylor’s affection in “Teardrops on My Guitar” has a soon-to-be superstar longing for him and he’s totally unaware. The standout from Swift’s debut LP boasts the type of nuanced songwriting that would eventually make Swift a sensation, and while the “I secretly like him but he likes her and he’ll never know how much I like him” dynamic is repeated throughout her catalog, “Teardrops” captures that resignation within a handful of striking images, most notably the title phrase.
7. Taylor Swift, «Blank Space»
There aren’t too many pop songs that turn on a dime in the middle of the second verse, but just as her unhinged character in the “Blank Space” video unravels midway through, so does Swift at the song’s center, diving into self-deprecation and mocking her well-documented romantic history outside of music. “Blank Space” works as far more than satire, though: snappy and uncluttered, it’s a fantastic sing-along dotted with quotable moments (“I can make the bad guys good for a weekend,” “Boys only want love if it’s torture”).
6. Taylor Swift, «Love Story»
It takes guts to name a song something as bold and straightforward as “Love Story,” but Swift’s breakthrough single makes good on the “story” part of the equation by unfolding a modern-day parable that somehow never slips over the edge into full-on cheese. Perhaps it’s the earnestness of Swift’s performance as a heroine searching for an escape route with her Prince Charming and finally realizing that reality can make room for their tale. Out of the millions of love stories in the history of pop music, “Love Story” stands out.
5. Taylor Swift, «Mean»
Simply put, a pitch-perfect rebuke of bullying. The Speak Now single posits that living well is indeed the best revenge, as Swift bashes her early detractor by predicting that her future is bright, while their future only contains minor victories (and a huge helping of meanness). Swift sings “Mean” in first person, but it’s not really for her — this is a song for people who feel belittled and beaten down by others, who look to someone like Swift for uplift and assurance. “Mean” is designed to shout along with cathartically, and it succeeds.
4. Taylor Swift, «State of Grace»
A bulldozer of an opening to Red, “State of Grace” is Swift’s most sonically towering track ever recorded; it’s a good thing that its author headlines arenas, because no small room could contain this song’s might. Instead of relying on lyrical detail, Swift stacks guitar lines upon propulsive drums and lets the whole thing rip; instead of opting for a wordy chorus, the hook here echoes with conciseness: “I never saw you coming/ And I’ll never be the same.” At nearly five minutes in length, “State of Grace” stays exhilarating start-to-finish and will be one of Swift’s most enduring non-singles ever.
3. Taylor Swift, «Dear John»
One of the (many) reasons any man should think twice about screwing over Taylor Swift: She is capable of penning a visceral, eviscerating takedown as potent as any hip-hop diss track. “Dear John,” a mangling of ex-beau John Mayer, is nearly seven minutes of simmering anger — but it never feels exploitative or unyielding, instead exploring the feeling of being taken advantage of and punctuating each chorus with a sorrowful “I should’ve known.” Swift uses “Dear John” to turn the gut-punch of being led astray into a clenched fist and declaration of survival. “I took your matches before fire could catch me,” Swift spits at her beloved-turned-enemy. And we, the listeners, simply get to sit back and watch the fireworks.
2. Taylor Swift, «Style»
“Style” is all about the details: the hints of the guitar lick in the verses, the echoing vocals of “out! of! style!” on the chorus, the tension in Swift’s voice when she debates telling her guy that it’s time to leave, the way “James Dean/daydream” and “red lip/classic” are perfect rhymes positioned on top of each other, the release of the “take me hooooome” on the bridge. On an album filled with very good-to-terrific pop songs, “Style” is the most finely manicured, the most well-produced, the most fully realized — and still, the most affecting. Decades from now, musical anthropologists will study how pop could be this perfect.
1. Taylor Swift, «You Belong With Me»
Throughout the twists and turns of her career, Swift has changed sounds, collaborators, personas and approaches, but has not — and perhaps will never — eclipse the magnificence of “You Belong With Me.” Credit the song’s simplicity, echoing the thematic concept of “Teardrops on My Guitar” but amplifying the high school heartache and polishing the hook so that it never floats back down after leaving the ground. There are so many things to love within “You Belong With Me,” from the high heels/sneakers dichotomy to that double handclap during the bridge, but more than anything, it’s quintessential Taylor, the ultra-relatable protagonist who can sum up complex feelings in a vocal run or quick turn-of-phrase. “You Belong With Me” has been her defining song for years, and that’s because it’s her best.
This article was originally published by: Billboard