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All 229 of Taylor Swift’s Songs, Ranked

From teen country tracks to synth-pop anthems and rare covers, a comprehensive assessment of her one-of-a-kind songbook through the Midnights era.

Taylor Swift

Ranking all 129 of Taylor Swift's songs (from "Tim McGraw" to the 'Reputation' era, Rob Sheffield writes, "the weirdest and most fascinating thing about Taylor Swift will always be her music."

Taylor Swift the celebrity is such a magnet for attention, she can distract from TAYLOR SWIFT THE artist. But Swift was a songwriter before she was a star, and she’ll be a songwriter long after she graduates from that racket. It’s in her music where she’s made her mark on history — as a performer, record-crafter, guitar hero and all-around pop mastermind, with songs that can leave you breathless or with a nasty scar. She was soaring on the level of the all-time greats before she was old enough to rent a car, with the crafty guile of a Carole King and the reckless heart of a Paul Westerberg — and she hasn’t exactly slowed down since then.

So with all due respect to Taylor the myth, the icon, the red-carpet tabloid staple, let’s celebrate the real Taylor — the songwriter she was born to be. Let’s break it down: all 229 tunes, counted from the bottom to the top. The hits, the flops, the deep cuts, the covers, from her raw 2006 debut as a teen country ingenue right up to Midnights

Every fan would compile a different list—that’s the beauty of it. She’s got at least 5 or 6 dozen songs that seem to belong in her Top Ten. But they’re not ranked by popularity, sales or supposed celebrity quotient — just the level of Taylor genius on display, from the perspective of a fan who generally does not give a rat’s nads who the songs are “really” about. All that matters is whether they’re about you and me. (I guarantee you are a more fascinating human than the Twilight guy, though I’m probably not.)

Since Taylor loves nothing more than causing chaos in our lives, she’s re-recording her albums, including the outtakes she left in the vault before. So far, she’s up to Fearless and Red. For the Taylor’s Version remakes, both versions count as the same song. It’s a tribute to her fierce creative energy — in the past couple years she’s released an avalanche of new music, with more on the way. God help us all.

Sister Tay may be the last true rock star on the planet, making brilliant moves (or catastrophic gaffes, because that’s what rock stars do). These are the songs that sum up her wit, her empathy, her flair for emotional excess, her girls-to-the-front bravado, her urge to ransack every corner of pop history, her determination to turn any chorus into a ridiculous spectacle. So let’s step back from the image and pay homage to her one-of-a-kind songbook — because the weirdest and most fascinating thing about Taylor Swift will always be her music.

From Rolling Stone US

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“Would’ve, Could’ve, Should’ve” (2022)

Taylor revisits the memory of her teenage self, with an adult sense of compassion. “Would’ve, Could’ve, Should’ve” is a powerful sequel to “Dear John,” but when she sang about this story before, her tone was more straightforward anger and regret. This song is messier, more confused, more ambivalent, as she struggles to understand the brash, complex 19-year-old artist/superstar/mirrorball she used to be. As she reflects, “I would have stayed on my knees/And I damn sure never would’ve danced with the devil at 19/And the God’s honest truth is that the pain was heaven.”Best line: “If I was some paint, did it splatter on a promising grown man?”