We're all under Taylor Swift's spell. From her poppy radio hits to her crying-on-the-floor anthems, her discography is as enthralling as it is extensive. She enchants with stories about not just heartbreak and lost loves, but also about wider reflections on life — self-worth, fame, politics, family, moving on, change.
Though Swift emerged as a country icon in high school, she has leapt across genres with ease in the years since, mastering them as well as shaping them. Whether she's busy conquering synth pop or molding indie folk, her songwriting cultivates a divine magic, one that merges reality and fiction with profound intimacy.
After expanding her sonic universe further with Midnights last year, Swift will kick off her "Eras Tour" in March. Simply the name of her tour indicates the expanse and power of her musical career thus far: as she bridges her eras, she builds her legacy.
Her legacy receives a unique nod through her four nominations for the 2023 GRAMMYs: while Swift is nominated for her Where The Crawdads Sing track, "Carolina," she's also nominated for songs that she wrote years ago, around the time of her original Red release. And just this month, Midnights' "Anti-Hero" broke Swift's personal record for her longest-running No. 1 single on the Billboard Hot 100, further proving that she hasn't lost her touch.
By cherishing her past while continuing to mold her musical future, Swift strikingly dominates with staying power. Ahead of the 2023 GRAMMYs and Swift's upcoming "The Eras Tour," here are 13 tracks that highlight Swift's evolution up to Midnights, honoring her trailblazing creativity and versatility.
"Our Song," Taylor Swift (2006)
A song about a song, how meta of Swift. One of her earliest meta songwriting moves, "Our Song" encapsulates a relationship's everlasting beauty with the warm breeziness of riding shotgun. Its lighthearted conversational lyricism emits an infectious joy that helped introduce Swift as a songwriter who is both relatable and captivating.
The banjo-led tune establishes the singer's country roots with a casual, but vivid image: Swift grinning with her elbow on the car door, hair windswept with the windows down. She may have written "Our Song" for a talent show back in high school, but Swift clearly had the songwriting prowess of a superstar — one that grew well beyond freshman year.
"White Horse," Fearless (2008)
Just two tracks after the whirlwind romance of "Love Story," Swift finds herself closing her fairytale storybook to disappointment. While "White Horse" sees the singer question her self-worth and cradle her crushed dreams, the heartbreaking track ended up earning Swift two GRAMMY Awards for Best Country Song and Best Female Country Vocal Performance in 2010. (The singer scored her first GRAMMY wins that year, taking home four GRAMMYs total. To date, Taylor Swift has won 11 GRAMMYs and received 42 nominations overall.)
Although the acoustic ballad wallows in sorrow, gloom eventually blooms into a necessary epiphany: "I'm gonna find someone someday who might actually treat me well," Swift realizes in the final chorus. In this way, "White Horse" prevails as one of the singer's most powerful ballads to date — and judging by what Swift has said about Midnights track "Lavender Haze," that realization has come true.
"Forever & Always," Fearless (2008)
"Forever & Always" is arguably one of Fearless' staple tracks, but what many fans may not know is that the timeless track almost didn't make the album. The pop-rock anthem track sees Swift denounce a hypocritical ex who misled her, and she criticizes them with a slew of questions she already knows the answers to: "Were you just kidding?" "Was I out of line?" "Did you forget everything?" From distress to confusion to anger, the song bursts with warranted rage at a betrayal, cementing Swift as a master of channeling heartbreak.
"Enchanted," Speak Now (2010)
Long before "Enchanted" spiraled into one of Swift's many viral TikTok moments, the Speak Now deep cut bewitched listeners from the second it arrived more than a decade ago. The song hums with anticipation, with early acoustic guitar later giving way to overwhelming yearning and anthemic production.
The way the song progresses is almost like a fairytale, starting with a longing stare and playful conversation before ending with a rosy-cheeked walk home. It's a near-perfect display of Swift's ability to capture an incisive, fleeting romance in song, from the smitten lyrics to cinematic production. And though the love song serves more of a captivating cliffhanger than a finished chapter, its story still leaves listeners blushing all the way home.
"Back To December," Speak Now (2010)
On Speak Now's "Back to December," Swift sifts through wilting roses and missed birthdays to unearth a sorrowful confession. As she comes to terms with her regret over ending a healthy relationship, the track swells with guilt and sincerity. While many of Swift's preceding romantic songs were characterized by longing or criticism, "Back to December" takes the rare form of a bittersweet, candid apology that exhibits maturity and grace.
"Mean," Speak Now (2010)
Complete with banjo and fiddle, "Mean" isn't just the only country-driven track on Speak Now, but it's also one of the last truly classic country songs of her catalog. The album's spunky sixth track goes down as one of Swift's most beautifully berating to date — even alongside "Look What You Made Me Do," "Bad Blood," and "Picture to Burn" — as she lambastes a cruel critic and realizes her self-worth.
Ironically, the Swift track that most put haters on blast is one of her most critically acclaimed, as the song won Swift two GRAMMY Awards for Best Country Solo Performance and Best Country Song in 2012. "Mean" also thrives as a manifestation — she has certainly become big enough that they can't hit her.
"Blank Space," 1989 (2014)
Nice to meet you, where you been? Swift's 1989 era submerged the singer in heavy synth and kaleidoscopic pop, and the record's exuberant second single "Blank Space" best flaunts Swift's multifaceted artist persona. The illustrious pop song satirizes the media's image of Swift as a serial dater, coasting with a sultry liveliness before escalating into ferocity.
Swift is scathingly and brilliantly self-aware as she acknowledges the world's view of her reputation: "Got a long list of ex-lovers/ They'll tell you I'm insane/ 'Cause you know I love the players/ And you love the game."
She continued poking fun at the "crazy ex-girlfriend" trope in the music video, from wrecking her former lover's car to setting his clothes on fire. The cleverly self-deprecating narrative (and genius visual) helped "Blank Space" become Swift's biggest streaming song to date, garnering a whopping 3 billion views on YouTube alone.
Accolades aside, "Blank Space" marked an important turning point for Swift. It was the first time she used her autobiographical songwriting style to take the power back — and most importantly, prove that no matter what is said about her, she'll keep cranking out the hits.
"Don't Blame Me," reputation (2017)
Defiance defines "Don't Blame Me," the fourth track from Swift's intrepid — and perhaps most unexpected — album reputation. The track personifies catharsis, uplifted by heavy bass and hard-hitting synth. Although the song is loosely about an intoxicating love, its ambition also represents Swift reclaiming her narrative once again.
Drawing comparisons to Madonna's "Like a Prayer" and Hozier's "Take Me to Church," the song marks more than moody melodrama, but shamelessly moving forward. Amid public quarrels with other celebrities — as well as the tabloids' obsession with her personal life — she makes a very definitive statement: don't blame her.
"Cruel Summer," Lover (2019)
"Cruel Summer" strikes Swift's discography in a zealous way, recalling the dreamy worlds of 1989's "Style" or reputation's "Getaway Car." The song sees Swift reminisce about a whirlwind summer romance with bittersweet intensity.
The track's assertive, immaculate electropop writhes irresistibly as Swift navigates the stark pain of secrets and love. Everything about "Cruel Summer" is sharp and exquisite, and the way its bridge bursts with melodramatic vigor is enough alone to make this a vital Swift track, even if it wasn't a single.
"the last great american dynasty," folklore (2020)
"the last great american dynasty" flourishes as one of Swift's most lucid, exquisite storytelling ventures — and as any Swiftie knows, that's saying something.
Reading like a short story, the crisp indie track recounts the life of American socialite Rebekah Harkness, one of the former owners of Swift's Rhode Island mansion. Swift weaves the past and present together seamlessly, drawing parallels between herself and Harkness with vivid detail and keen clarity. On this folklore track, Swift presents a refreshing creative vision by flaunting a new, innovative facet of her songwriting prowess.
"betty," folklore (2020)
Swift's first indie-folk foray, folklore, spins a tantalizing fictional love triangle across three tracks: "cardigan," "august," and "betty." The latter shimmers with reflective hope and heartache from the perspective of a character named James.
The apologetic, harmonica-driven folk rock track is reminiscent of Swift's earlier, country-rooted music — yet, the way its intricate narration uniquely interlocks with other album tracks is more characteristic of Swift's modern storytelling craft. Swinging between lighthearted and forlorn, "betty" cements Swift as a mystical mastermind.
"All Too Well (10 Minute Version) (Taylor's Version) (From The Vault)," Red (Taylor's Version) (2021)
Swift's "All Too Well (10 Minute Version)" might very well be her magnum opus. Although the original beloved song from Red was never released as a single, it emerged as a fan favorite for its tragic retelling of visceral heartbreak. And once Swift released a new — and much longer — 10-minute edition of the gut-wrenching track on Red (Taylor's Version) nearly a decade later, it almost instantly became the fan favorite.
The song broke the Guinness World Record for being the longest song to reach No. 1 on Billboard Hot 100 (beating out Don McLean's "American Pie"!), and its cinematic music video "All Too Well: The Short Film" continued to stretch the Swift multiverse. With lucid lyricism, cathartic storytelling, and riveting melodies, "All Too Well (10 Minute Version)" triumphs as the pinnacle example of everything that makes Swift a revered songwriter and certified star — one who continues to shine like an ever-lovely jewel.
"Anti-Hero," Midnights (2022)
"It's me, hi, I'm the problem, it's me," Swift sighs on "Anti-Hero." Self-hatred takes center stage on the lead single from Midnights, inspired by the singer's insecurities, nightmares and fear of depersonalization.
Over a swirl of steady upbeat production, the pop song draws comparisons to the heartbreaking honesty of Lover's "The Archer." Her poetic candor takes on a self-destructive quality ("I'll stare directly at the sun but never in the mirror," she admits) that conveys an all-consuming loneliness — and at the same time, stark self-awareness.
Yet, Swift isn't an anti-hero, she's a mastermind. Serving as a "guided tour" of the things she tends to hate about herself, "Anti-Hero" spotlights not only the weight of Swift's vulnerability, but also its power. This capability transcends beyond Midnights; her sweeping creative force stretches across her past records and conquered genres. And even despite any insecurities, her influence has only continued to grow — showing that Taylor Swift will never go out of style.
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