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From: Red (Taylor’s Version)

Co-written with Train’s Pat Monahan and eventually given to Sugarland (who received guest vocals from Swift on their version), Swift’s version of “Babe” offers levity on the Red (Taylor’s Version) track list, even in the context of a breakup song. Swift and Jack Antonoff produce a warm mix of keys, slide guitar and percussion, re-creating the glow of Swift’s turn-of-the-decade country-pop that rolls downhill as the lyrics look back on personal missteps.

From: Fearless (Taylor’s Version)

Taylor Swift spent part of her Fearless album era opening for Keith Urban on tour; over a decade later, Urban has joined forces with Swift for “That’s When,” the only proper duet of the six “From The Vault” songs on Fearless (Taylor’s Version). Despite being a post-breakup song, “That’s When” offers a dose of levity, as the pair of country pros hammer out their differences over unfussy pop production and then join together for some giddy harmonizing.

From: Red (Taylor’s Version)

“Forever Winter” combines one of the more intricate productions of Red (Taylor’s Version) with a nuanced, wide-ranging vocal take from Swift. She races through lines, then lingers on syllables, and minimizes her voice to a whisper then blows out the chorus, as horns, flutes and guitars swirl around her voice. The concern cuts through it all: Swift sings toward someone she hasn’t been able to read, and grasps at ways to help him out of the dark.

From: Fearless (Taylor’s Version)

Don’t be shocked if you find yourself crooning along to “Bye byyyye, babyyyyy” after first hearing the final “From The Vault” song on the Fearless (Taylor’s Version) track list. “Bye Bye Baby” is yet another catchy-as-hell kiss-off from Swift, but this one hits its stride in its second half, when the production drops out and Swift morphs the chorus into a mantra for her own benefit: “Bye bye, to everything I thought was on my side.”

From: Red (Taylor’s Version)

Although Ed Sheeran was featured on the Red single “Everything Has Changed,” Swift’s Folklore/Evermore era didn’t feature an assist from her fellow stadium-playing superstar. “Run” is a belated means of amending that, so to speak: although the song has been saved from the vault, Aaron Dessner’s co-production recalls Swift’s recent foray into indie-folk. And the rustic sound fits the duet pair nicely, a twiddling guitar lick and orchestral gestures popping up amongst breathless romantic gestures.

From: Speak Now (Taylor’s Version)

In the late 2000s, around the same time Swift was becoming a star in the country world, Hayley Williams’ band Paramore was triumphantly straddling the pop-punk and emo scenes with hits like “Misery Business” and “That’s What You Get”; both artists have existed in the public eye for well over a decade, and both have had to react to various backlashes that are a natural symptom of superstardom. As a meditation on collapsing alliances and irrational behavior, “Castles Crumbling” remains ambiguous but rings true, with the production brimming with ethereal voices and Swift and Williams maintaining mournful attitudes as they examine their personal wreckage.

From: Speak Now (Taylor’s Version)

“You know how to keep me waitin’ / I know how to act like I’m fine,” Swift declares on “Foolish One,” a heartbreak tale (Swift herself is the titular character, betting big on the wrong guy) which most closely recalls the refinement of her country-pop sound in the leap from Fearless to Speak Now, but stretches out, filling five minutes and change with warning signs and sorry realizations. The lyrical details, from the early attempts to appear unbothered to the bitter pill of “I’ll get your longing glances, but she’ll get your ring,” are worth getting lost in, and Swift’s vocal take strikes an affecting balance between chastising and hurt.

From: Red (Taylor’s Version)

A few songs before the 10-minute kiss-off to end all kiss-offs on the Red (Taylor’s Version) track list, Swift gives us another not-so-fond farewell to an oblivious rich kid on “I Bet You Think About Me,” a free-wheeling and lushly produced jam alongside Chris Stapleton. One of Swift’s more subtle attributes as a performer is how funny she can be — even more so than Stapleton’s soulful vocal assists or the harmonica runs, Swift deadpanning lines like “The girl in your bed has a fine pedigree / And I’ll bet your friends tell you she’s better than me / HEH!” is the highlight here.

From: Fearless (Taylor’s Version)

“Oh, I hate those voices telling me I’m not in love anymore,” Swift sings on the crucial bridge to “We Were Happy,” a quiet reflection of a romance that wasn’t perfect, marked by a chiming guitar and a vocal performance oscillating between nostalgia and guilt. The care that Swift takes in that performance lifts “We Were Happy” off the ground, as she looks back on the relationship’s high points and pleads with herself to find a way back.

From: Red (Taylor’s Version)

Dizzying memories of inadvertent love sparkle on “The Very First Night,” a piece of blissful bubblegum that sounds at home next to Red songs like “22” and “Stay Stay Stay.” As is often the case, the high points come from the lyrical details — Swift remembering casual words that end up meaning the world, and wishing she could go back in time to perfect the scene — but the danceable country-pop stomp is handy for those who simply want to move around to a starry-eyed anthem.

From: Speak Now (Taylor’s Version)

“Electric Touch” follows a long line of Swift songs in which her painful experiences in love are forcing her to keep her guard up as a new romance begins — but the excitement of the unknown, the fact that “This could either break my heart, or bring it back to life,” keeps her hopeful. Fall Out Boy’s Patrick Stump joins her cautious optimism, and as they play two souls trying to become intertwined, his jittery soul pairs splendidly with Swift’s more straightforward delivery, especially as his higher register repeats “Just! One! Time!” in the bridge.

From: Fearless (Taylor’s Version)

The guitars, fiddles and harmonica on “You All Over Me” all harken back to Swift’s country beginnings, but the lyrical focus on this Maren Morris collaboration demonstrates what set the singer-songwriter apart at a young age. Swift can’t get over an ex, his memory imprinted on every piece of her surroundings; this feeling is gracefully acknowledged and captured in glistening detail, with Morris backing up Swift’s admission that “no amount of freedom gets you clean.”

From: Speak Now (Taylor’s Version)

An epic love poem that muses on star-crossed romance, harkens back to Swift’s grandparents and declares that soul mates will always collide, circumstances be damned, “Timeless” functions as both a ready-made fan favorite — pity any Swifties who can’t get immersed in this dreamy, destiny-filled atmosphere — as well as a demonstration of Swift’s songwriting gifts. She deftly positions tiny gestures and thoughts within a much greater tapestry of generations-defying emotion, each knickknack in an antique shop just as important as the statement, “I believe that we were supposed to find this.”

From: Fearless (Taylor’s Version)

A perfect pop eye-roll: “Mr. Perfectly Fine” is not so much a testament of heartbreak as much as a declaration against an annoying dude, with Swift brushing off an ex whose phoniness was able to upend her most naive self. Along with sonic similarities to Swift’s Fearless and Speak Now eras — listen to the punch of those country-pop drums! — “Mr. Perfectly Fine” lets Swift pay homage to some of her grandest breakup songs, as back-to-back lines in the chorus reference “All Too Well” and “Dear John,” respectively.

From: Red (Taylor’s Version)

The song that Swift sent to Little Big Town — and ultimately became a Hot Country Songs chart-topper for the quartet upon its 2016 release — finally receives a tender rendition from its songwriter, as Swift refracts the tale of post-breakup pain back through her own lens. The harmonies that made “Better Man” a Little Big Town standout are honored here, as Caitlin Evanson and Liz Huett provide backing vocals to Swift’s dashed dreams.

From: Red (Taylor’s Version)

Between Punisher, Folklore and Evermore, Phoebe Bridgers and Taylor Swift offered some of the most incisive and affecting songwriting of 2020 — and while Swift is the sole scribe on “Nothing New,” the revived track works pristinely as a shared showcase for both artists’ lyrical sensibilities. Amidst understated cello and violin, Swift and Bridgers trade slicing lines and rhetorical questions about unfair social expectations on young women (“How did I go from growing up to breaking down?” is a knockout punch) before ruminating on a meeting with the next generation: “She’ll know the way and then she’ll say she got the map from me / I’ll say I’m happy for her, then I’ll cry myself to sleep.”

From: Speak Now (Taylor’s Version)

A few years after using her duel Folklore/Evermore eras to create new worlds as a narrator instead of the star, Swift returns to this gorgeously rendered character study that centers a captivating girl named Emma, whose considered approach to relationships deepens with each new verse. “She won’t lose herself in love the way that I did,” Swift sings with a tinge of envy, as the production that she co-created with Aaron Dessner oscillates between stately piano balladry and swaying country-pop; “When Emma Falls In Love” whirs with lyrical complexity and sonic detail, as Swift brings her recent song craft back into the vault.

From: Red (Taylor’s Version)

Red was the first album in which Swift worked with Max Martin, and the pairing between the superstar and legendary producer resulted in smashes like “We Are Never Ever Getting Back Together” and “I Knew You Were Trouble.” Martin’s only credit in the “From The Vault” tracks on Red (Taylor’s Version) here comes as a co-writer on “Message in a Bottle,” a compact, propulsive dance track that belatedly became a radio hit, and carries the same energy (and crackling charm) as the singles that pushed Swift’s sound toward mainstream pop leading into 2014’s 1989.

From: Fearless (Taylor’s Version)

If you entered Fearless (Taylor’s Version) searching for a synthesis of the country-pop writing charm that defined Swift’s early albums and the ultra-confident song construction of her most recent works, “Don’t You,” an unreleased track from the Fearless era that has been given a modern facelift by Swift and Jack Antonoff, represents the most satisfying version of that amalgam. While the running-into-an-ex storytelling and clever lyricism fit snugly into the project that made Swift a superstar, the sonic landscape — keyboards, electric guitars, drums that stack upon each other — and Swift’s yearning, dazzlingly sophisticated performance elevate “Don’t You” more than a decade later.

From: Speak Now (Taylor’s Version)

The best “From The Vault” songs exist in conversation with their years-old host albums as well as the most recent innovations in Swift’s career, specifically as a producer — and “I Can See You,” the most thrilling never-before-heard track here, riffs on the chance encounters and flirtations of Speak Now by amplifying the sexual energy, and providing a forward-looking instrumental foundation with plenty of bite. Every choice within “I Can See You,” from that surf-rock guitar riff to Swift’s most delicious innuendos (“You won’t believe half the things I see inside my head,” she deadpans) to the way the pre-chorus leaves the ground and flies to the hook, is deployed with utmost confidence, as Swift and Jack Antonoff understand precisely the tone that the song needs to convey to fully work. “I Can See You” would have been an excellent addition to the original Speak Now, but there’s no doubt that Swift’s current skill set made the song even better for Speak Now (Taylor’s Version).

From: Red (Taylor’s Version)

One can certainly pore over the lyrics — a profane keychain? A missed 21st birthday? Who was “some actress”?? — of this super-sized version of what was already a magnum opus on the Red track list, and rightfully so; Swift understood that her fans would simultaneously embrace and investigate every detail of one of her most famous breakup songs. Yet the 10-minute “All Too Well” deserves to be celebrated not just for the Easter eggs, but for the story that they comprise. Like the original version released in 2012, the extended “All Too Well” is a towering songwriting achievement, made even more impressive now as its tale of misbegotten love never flags or sounds overstuffed across its mammoth run time. The production hums along, each line pierces skin, and Swift is at her most commanding — she gave the mainstream an impossibly long Hot 100 chart-topper, and her most ardent supporters her full, unvarnished truth.