Caroline Darney
April 18, 2024 12:22 pm ET
It’s the week of April 19, which means we’ve made it. New Taylor Swift music will hit the airwaves on Friday with the release of The Tortured Poets Department. It’s Swift’s 11th studio album and has been highly anticipated since the singer-songwriter announced it at the Grammy Awards.
MORE: All the Taylor Swift Tortured Poets Department bonus tracks and variations that have been announced
In order to prepare for the onslaught of new music, we are taking on the frankly impossible challenge of ranking the 14-time Grammy winner’s 40 best songs. This is the opposite of whatever you would deem scientific as this list would likely shift slightly if we undertook the same project next week.
Let’s get to it. Here are songs 30-21. Each day before the album release, we’ll give you the next 10 until we get to No. 1. Click here to see songs 40-31, the rankings of 30 through 21 and our songs 20-11.
10. Love Story (Taylor's Version)
Album:Fearless (Taylor’s Version)
Although there were a handful of popular Swift songs prior to this (namely “Teardrops On My Guitar,” “Tim McGraw” and “Our Song” from her debut album), this song felt like a truly pivotal moment in her career. It’s much more pop-sounding, and it’s a song that has had staying power. It is also adorable that it has become one of Travis Kelce’s favorites.
Best Lyric:
Romeo, take me somewhere we can be alone
I’ll be waiting, all there’s left to do is run
You’ll be the prince and I’ll be the princess
It’s a love story, baby, just say, “Yes”
9. Out Of The Woods (Taylor's Version)
Album:1989 (Taylor’s Version)
The beat. The lyrics. The bridge. “Out Of The Woods” is a nearly perfect song, on one of my personal favorite albums in 1989.
Best Lyric:
Remember when you hit the brakes too soon?
20 stitches in a hospital room
When you started crying, baby, I did too
But when the sun came up, I was looking at you
Remember when we couldn’t take the heat?
I walked out, I said, “I’m setting you free”
But the monsters turned out to be just trees
When the sun came up, you were looking at me
8. Getaway Car
Album:Reputation
Reputation at its best. Another phenomenal bridge matched with that Reputation era beat and vibe. If you don’t find yourself yell-singing “I LEFT YOU IN A MOTEL BAR” are you truly even living?
Best Lyric:
We were jet-set, Bonnie and Clyde (oh-oh)
Until I switched to the other side, to the other side
It’s no surprise I turned you in (oh-oh)
‘Cause us traitors never winI’m in a getaway car
I left you in a motel bar
Put the money in a bag and I stole the keys
7. Dear John (Taylor's Version)
Album:Speak Now (Taylor’s Version)
“Dear John” is a heartbreaking and heartfelt ballad about the pain of losing love. It goes so far beyond just a sad song about an ex, but the masterful lyrics and inclusion of someone’s tell-tale guitar riff to open the song are just art.
Best Lyric:
You paint me a blue sky
And go back and turn it to rain
And I lived in your chess game
But you changed the rules every day
Wondering which version of you I might get on the phone tonight
Well, I stopped picking up and this song is to let you know why
6. Don't Blame Me
Album:Reputation
Taylor Swift seemingly has a song for every feeling, and with “Don’t Blame Me,” she encapsulates the all-consuming feeling an obsessive relationship can take on. If your love doesn’t feel like a drug, are you even doing it right? Add in those Reputation vibes and beats, and it’s art. Oh, and if you haven’t watched the “Don’t Blame Me” transition into “Look What You Made Me Do” from the Eras Tour, stop what you’re doing and watch it right now.
Best Lyric:
My name is whatever you decide
And I’m just gonna call you mine
I’m insane, but I’m your baby (your baby)
Echoes (echoes) of your name inside my mind
Halo, hiding my obsession
I once was poison ivy, but now I’m your daisy
5. Style (Taylor's Version)
Album:1989 (Taylor’s Version)
A radio bop that is just so infectious. “Style” just has it all. It’s that story of knowing the guy isn’t right but also who cares because it’s perfect in the moment. You’re not a match but you can’t resist the feelings. Plus it’s just so catchy.
Best Lyric:
Midnight
You come and pick me up, no headlights
Long drive
Could end in burning flames or paradise
4. Delicate
Album:Reputation
Honestly, an utterly devastating song. Around the time that Reputation released, Swift had taken a lot of criticism in the press about everything: her music, her personality, her love life and more. She had the ongoing battle with Kim Kardashian and Kanye West releasing privately recorded audio.
“Delicate” — and the music video — deal with feeling so under the microscope.
Best Lyric:
This ain’t for the best
My reputation’s never been worse, so
You must like me for me
3. You're Losing Me (From The Vault)
Album:Midnights
BUCKLE UP, FRIENDS. If “You’re Losing Me” is any indication of the soul-ripping content we might be getting with The Tortured Poets Department, none of us are prepared. It details that phase where you know your relationship is starting to fall apart but you don’t know what to do to resuscitate it. From the heartbeat background to the biting lyrics, “You’re Losing Me” is some of Swift’s best work.
Best Lyric:
Fighting in only your army
Frontlines, don’t you ignore me
I’m the best thing at this party
(You’re losin’ me)
And I wouldn’t marry me either
A pathological people pleaser
Who only wanted you to see her
And I’m fadin’, thinkin’
2. Cruel Summer
Album:Lover
A song released in 2019 became the song of the summer in 2023. That’s the power of “Cruel Summer.” Initially going to be pushed in spring of 2020, “Cruel Summer” became lost to the pandemic before a resurgence last year. It also earned its spot as the first full song of the Eras Tour setlist.
Best Lyric:
I’m drunk in the back of the car
And I cried like a baby coming home from the bar (oh)
Said, “I’m fine, ” but it wasn’t true
I don’t wanna keep secrets just to keep you
1. All Too Well (10 Minute Version) (Taylor's Version) (From The Vault)
Album:Red (Taylor’s Version)
OH BOY. Was there ever any doubt what would be in the top spot? When Swift released Red (Taylor’s Version), fans were simultaneously floored and obsessed with the extended version of “All Too Well.” It’s 10 minutes of devastation and broken hearts, and it’s perfect.
Best Lyric:
And maybe we got lost in translation
Maybe I asked for too much
But maybe this thing was a masterpiece ’til you tore it all up
Running scared, I was there
I remember it all too well
And you call me up again just to break me like a promise
So casually cruel in the name of being honest
I’m a crumpled up piece of paper lying here
‘Cause I remember it all, all, all
Too well
