122–100 99–75 74–50 49–25 24–1
74. “I Forgot That You Existed”
This unique perspective on a failed relationship finds relief in indifference, rather than bitterness or regret.
73. “Breathe”
Colbie Caillat’s backing vocals and co-writing credits earned her the honor of being the first-ever featured artist on a Taylor Swift song. It’s a well-crafted, soft-spoken ballad that’s placed perfectly within Fearless’ tracklist, providing a brief respite from the album’s flurry of high-energy pop and emotional turmoil
72. “How You Get the Girl”
With glittery acoustic guitars and simple drum programming, this 1989 song could have easily fit on Red.
71. “Ours”
A straightforward love song that definitely should have been included on Speak Now’s standard edition instead of being thrown in as a bonus track. This is the kind of song that practically begged YouTubers to cover it on the ukulele.
70. “I Know Places”
A rare minor-key anthem. I think her use of “damn” here may have been the strongest language she’d used thus far.
69. “Sweeter Than Fiction”
I have literally never heard of the movie One Chance (which is where this song originated), but the chorus and guitar solo go hard here.
68. “Shake It Off”
1989’s horn-heavy lead single is the least representative song of the album’s overall synthpop style. But Swift’s move from the bleachers to the cheer team in this song’s video is a perfect metaphor for her mainstream pop breakthrough.
67. “London Boy”
This sweet burst of anglophilia samples Cautious Clay’s “Cold War,” and adds ridiculous orchestration to great effect.
66. “The Story of Us”
A little pop-punk influence combines with Speak Now’s straightforward country-pop aesthetic to create a song that’s like if Paramore covered Journey’s “Any Way You Want It” and added a banjo.
65. “The Best Day”
A sweet, simple tribute to a happy childhood and the parents who made it possible.
64. “I Wish You Would”
One of the better 1989 deep cuts was constructed in an unusual way: Jack Antonoff had a nearly-complete instrumental before Taylor began any work on it. Also, it’s 2 a.m. again.
63. “Hey Stephen”
This song is a bit of a paradox –– she still sounds relatively immature, but exudes more confidence on this one song than on her entire debut album.
62. “Ready for It?”
The bombastic, elegant chorus makes up for the ill-advised (but somewhat fun) pseudo-rap verses and immediately-dated EDM production.
61. Wonderland
A bonus track that’s better than half of the standard tracks on 1989.
60. “Don’t Blame Me”
If Hozier made EDM, it’d sound something like this.
59. “Fifteen”
It’s never too early for retrospection. At 18, Taylor’s already reflecting on the naivety of 15. She actually manages to sound a little older and wiser than she did on her previous album as she realizes the value of being alone.
58. “This Is Why We Can’t Have Nice Things”
Woozily pleasant production and catchy hooks battle with some of Taylor’s cringiest victim-complex lyrics. With different words, this would be one of Reputation’s undisputed highlights.
57. “Everything Has Changed”
Definitely the better of the two Ed Sheeran collaborations. This song is one of the most wholesome in both artists’ discographies, though it doesn’t give Sheeran much to do.
56. “Change”
Fearless’ closing song cleverly echoes its opening title track in tempo and tone, providing a strong sense of cohesion and closure to the album that secured Taylor Swift as a bonafide pop star.
55. “Dear John”
The saddest possible way of correctly observing that 31-year-old John Mayer probably shouldn’t have dated a 19 year old.
54. “Miss Americana and the Heartbreak Prince”
Taylor’s idea of getting political is turning American partisanship into high school drama. It’s kind of a dumb conceit, but the sonic aesthetic sounds a lot like Lana Del Rey’s early work, and the bridge is clever enough to justify the concept.
53. “Should’ve Said No”
You have to feel sorry for Taylor –– based on songs like this, it seems that her boyfriends have cheated on her since day one.
52. “Look What You Made Me Do”
This is not even close to her best song, but it’s one of her boldest. Its weirdness cannot be understated –– Taylor basically takes on a Disney villain persona while overtly referencing Kanye and sampling “I’m Too Sexy” as a blaring sax-synth combo pulses in the background. The bridge is god-tier pop production.
51. “Our Song”
The most radio-friendly hit of her self-titled debut cherishes the imperfections in a relationship.
50. “King of My Heart”
Some of the best percussion of Taylor’s discography comes in the chorus. It’s like a Phil Collins remix.
