Pop

Album: Lover
Year: 2019
Hot 100 Peak: No. 2

While a fun song with a cute message, “Me!” is far from the best showcase of Swift’s lyrical and musical prowess on Lover — in fact, it isn’t even the most obvious choice for lead single on the album’s tracklist. For years after the LP’s release, fans would gripe that the far superior “Cruel Summer” was never given the lead song treatment, instincts that would age well when the track unexpectedly reached No. 1 on the Hot 100 four years after it originally dropped. Swift herself didn’t even include “Me!” on her Eras Tour setlist in 2023, making it the only one of her album leads that didn’t make the cut.

Album: Evermore
Year: 2020
Hot 100 Peak: No. 1

“Willow” is one of Swift’s catchiest tunes, and the witchy music video makes it even better. The disadvantage here is the inevitable comparison listeners were bound to make between “Willow” and Folklore lead single “Cardigan,” with the former’s Etsy-throw-pillow one-liners — “I come back stronger than a ’90s trend” being the main offender — paling in comparison to the gutting, masterful songwriting on the latter.

Album: Reputation
Year: 2017
Hot 100 Peak: No. 1 (three weeks)

Using snakes to hint what was coming, Swift insinuated that her newest single was going to involve some spite, and that’s exactly what we got with this hauntingly bitter, bass-thumping tune. If there had been any question that Swift may go back to her country roots, this is a pretty solid confirmation that the innocent, sparkly guitar-playing Swift isn’t making a return (she did declare that the old Taylor was dead, after all).

Album: The Tortured Poets Department
Year: 2024
Hot 100 Peak: No. 1 (two weeks)

For a fortnight there, “Fortnight” topped the Hot 100 — and for good reason. The simmering, scornful track beautifully blends Swift’s vocals with Posty’s and builds up to a gorgeous melodic bridge that makes you want to hear it again and again, serving as the perfect first taste of Tortured Poets.

Plus, Swift’s gothic self-directed video for the project is one of her best, winning video of the year at the 2024 VMAs.

Album: The Life of a Showgirl
Year: 2025
Hot 100 Peak: No. 1 (TBD)

Any number of the songs on Showgirl could have easily served as the lead single, with Swift reuniting with Max Martin and Shellback to pack the album full of pop radio-ready bangers. But there’s something particularly magical about this ultra catchy and quotable love song describing the singer’s romance with Travis Kelce — especially considering the full-circle moment of it arriving nearly two decades after Swift first referenced Shakespeare in a lovey-dovey lead single.

Album: Taylor Swift
Year: 2006
Hot 100 Peak: No. 40

For a girl who was just getting her start in the songwriting business (while her friends were busy doing high school homework), Swift’s lyricism and smooth vocals on “Tim McGraw” are highly impressive. Perhaps the only issue with it is that both her songwriting and singing have consistently improved throughout the subsequent 11 years.

Album: Red
Year: 2012
Hot 100 Peak: No. 1 (three weeks)

Swift was technically still considered country at this point in her career, but her initial single from Red definitely pointed towards the eventual pop direction she’d take, adding a little more sass than she had ever brought before (like, ever). Most of her pre-Red breakup songs had a sense of despair and sadness, but there’s absolutely none of that in this farewell tune, which makes it all the more desirable to those who are looking for a way to tell their exes off for good — Swiftie or not.

Album: Speak Now
Year: 2010
Hot 100 Peak: No. 3

Swift had shown that she’s a master at writing love songs with her first two albums, but the first single from her third album showed that she was nowhere near finished writing them — and getting better and better at it. “Mine” is as cute as they come, telling the tale of a couple who are taking on the world together, closing out the spirited chorus with a perfectly mushy-gushy love song line: “You are the best thing that’s ever been mine.”

Album: Folklore
Year: 2020
Hot 100 Peak: No. 1

Aside from “Cardigan” being one of the most beautiful-sounding songs in Swift’s catalog, and aside from it also containing some her most moving songwriting to date, this track was the perfect choice to introduce people to the Folklore cinematic universe. It perfectly sets up the complex, nuanced love triangle between characters James, Betty and August/Augustine through some of the most haunting lyrics the singer has ever penned, including: “I knew everything when I was young/ I knew I’d curse you for the longest time/ Chasing shadows in the grocery line/ I knew you’d miss me once the thrill expired/ And you’d be standing in my front porch light.”

Album: Midnights
Year: 2022
Hot 100 Peak: No. 1 (eight weeks)

For all intents and purposes, “Anti-Hero” should be the least relatable song on Swift’s discography. Not many people, for instance, can relate to the gargantuan responsibility of being globally famous, or to dreaming about one’s future daughter-in-law killing them for financial gain. But somehow, she made one of the most honest, self-effacing accounts of what it’s like to be the biggest pop star on the planet feel accessible to the general public — a feat that can be chalked up in part to her ability to infuse her clever sense of humor into hooks like “It’s me, hi, I’m the problem, it’s me.”

Album: 1989
Year: 2014
Hot 100 Peak: No. 1 (four weeks)

Ditching the banjos and country twang, Swift introduced her new pop sound with this sick beat – and a chorus that makes singing (and dancing) along unavoidable. While parts of Red showcased a bolder, almost more confident side to Swift, 1989 as a whole proved her to be practically invincible (especially after that album of the year Grammy). That’s immediately apparent from the moment the pounding bass begins in “Shake It Off” and is further solidified through the hater-dismissing lyrics. This is one of those gems that even those in the worst moods can’t help smiling and shaking along to.  

Album: Fearless
Year: 2008
Hot 100 Peak: No. 4

If “sophomore slump” was even still a thing in 2008, Swift’s Fearless certainly didn’t fall into that curse, and she established that straight out of the gate with this Romeo-and-Juliet-tributing anthem. Starting out with an enchanting banjo, the track’s awe-inspiring series of building melodies (and sweet story line) make for quite the happy ending and belt-worthy finale. While it may not necessarily be her catchiest single to date, a then-teenage Swift crafted a song that made people of all ages want to find their own love story — in under four minutes — and that is the sign of true musical genius.