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    • Tim McGraw. This introductory, career-establishing single certainly counts as a simple pleasure now, against all the more sophisticated writing she’s done since.
    • You're on Your Own, Kid. In case there was any doubt that it’s unresolved childhood loneliness and rejection that make the greatest breeding ground for uber-driven superstars, Swift clears it all up for us by effectively conceding as much in this childhood origin story for her ambition and independence.
    • Enchanted. Swift takes a backstage introduction to an indie-pop dude she had a crush on and turns it into something that feels like an epic moment at a royal ball.
    • Miss Americana and the Heartbreak Prince. Swift has been surprisingly unafraid to boldly speak out about political matters in recent years, after being criticized for staying quiet in her early career.
    • "Snow on the Beach" feat. Lana Del Rey. This Lana Del Rey collaboration initially didn’t feature much of LDR’s voice beyond some quiet background vocals.
    • "Maroon" A fan-favorite Midnights deep cut, “Maroon” scored a No. 3 placement in spite of not being an official single.
    • “Now That We Don’t Talk (Taylor’s Version) [From the Vault]” “Now That We Don’t Talk (Taylor’s Version) [From the Vault]” from the No. 1-debuting album 1989 (Taylor’s Version) hit No. 2 on the Hot 100 in November 2023.
    • "Fearless" Fearless‘ title track braved a No. 9 peak.
    • Kevin Jacobsen
    • 2021
    • 27 min
    • Love Story’ (2008) Album: “Fearless” Songwriter: Taylor Swift. Accolades: “Love Story” took Best Music Video at the CMT Music Awards and the Country Music Association Awards.
    • Blank Space’ (2014) Album: “1989” Songwriters: Taylor Swift, Max Martin, Shellback. Accolades: Right after “Shake It Off,” Swift earned another no. 1 here, becoming the first woman in history to succeed herself at the top of the charts, and scored Grammy bids for Record of the Year, Song of the Year and Best Pop Solo Performance for the song.
    • Shake It Off’ (2014) Album: “1989” Songwriters: Taylor Swift, Max Martin, Shellback. Accolades: The song instantly went to number-one on the Billboard Hot 100 and earned Grammy nominations for Record of the Year, Song of the Year and Best Pop Solo Performance.
    • You Belong with Me’ (2009) Album: “Fearless” Songwriters: Taylor Swift, Liz Rose. Accolades: Swift broke through at the Grammys when this song was nominated for Record of the Year and Song of the Year, the same ceremony where “Fearless” won Album of the Year.
    • Rania Aniftos
    • "Look What You Made Me Do" (Reputation, 2017) Why It’s Era-Defining: Sure, “Look What You Made Me Do” is polarizing — there’s a reason it’s No. 100 on this list — but you can bet every fan who calls themself a Swiftie remembers where they were when the music video for the Reputation lead single dropped.
    • "Forever and Always" (Fearless, 2008) Why It’s Era-Defining: The scathing ode to teenage heartbreak came amid Swift’s string of famous heartthrob boyfriends, whom she’d later write songs about.
    • "Dress" (Reputation, 2017) Why It’s Era-Defining: As confrontational as Reputation was in spots, the album’s real jaw-dropping moment came with “Dress,” the most explicitly seductive song to appear on a Taylor Swift LP to date.
    • "Haunted" (Speak Now, 2010) Why It’s Era-Defining: “Haunted” is one of Swift’s deep cuts that’s most fiercely loved by longtime fans. Mysterious and whimsical, it captures a darker strain of the magical themes the country-pop star perhaps unintentionally infused in the Speak Now era — and just as delightfully, it summarizes Bella Swan’s POV in New Moon of the Twilight saga with perfect accuracy.
    • All Too Well’ (10-minute version) There’s no mistaking it: “All Too Well” is Swift’s crown jewel. Even though the original tune was 11 years old, the release of a 10-minute version was worth it.
    • Enchanted’ ‘Enchanted’ is Swift’s most, well, enchanting entry in her catalog. There’s just something magical about it, from the doting lyrics to the windswept production.
    • Clean’ Taylor Swift’s ‘Clean’ doesn’t get enough credit for perfectly capturing the fall from grace and a relationship’s dying out. “You’re still all over me like a wine-stained dress I can’t wear anymore,” she coos.
    • invisible string’ There’s a belief that fate operates like a piece of string, knotting two lovers to one another. That’s the emotional core of ‘invisible string,’ in which Taylor Swift muses on past romantic failures, the healing process, and her then-relationship with Joe Alwyn.
  1. Apr 14, 2024 · Taylor Swift has charted with 231 songs, 49 Top 10 hits and 11 No. 1 smashes. In anticipation of her 11th album, we ranked her 11 No. 1s.

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  3. Apr 19, 2024 · With her 11th studio album The Tortured Poets Department out now, it’s a good time to refresh the ranking of Taylor Swift’s best 50 songs, which was originally published in early 2021.

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