The best song on every Taylor Swift album from Fearless to Midnights

ByQuyen Anne

Jan 11, 2024

In celebration of Midnights, here’s my take on the best song from each Taylor Swift album, based on lyrics, music, and enjoyability to sing and play on guitar. There were some close calls in these cases I called on techniques like putting songs on repeat and asking which one I’d be happy to listen to over and over (most fun I ever had).

I discovered her music during lockdown and exclusively chose her songs to learn on my guitar, which I dusted off, restrung and started over with. I haven’t listed a favorite song from her first album because I haven’t listened to it yet – I wanted to give each album space rather than rushing through them all.

So, here goes!

Fearless (2008)

Favorite song: Forever & Always

There several other contenders on the album (BreatheFearlessYou Belong With Me) but I think that Forever & Always is probably her best work here for its consistency and emotional energy. Like many of her later songs (and unlike most pop music) the song avoids slumping or feeling repetitive at any point.

Lyric highlight:

So here’s to everything coming down to nothing

Here’s to silence that cuts me to the core

Interesting versions: Forever & Always (Piano Version) has a slower tempo and an extended bridge, providing a nice alternative to the more energetic album version. On the other hand, the live version (featured strongly in the Journey to Fearless documentary) involves young TayTay throwing an armchair onstage. Ohhhhh (*throws chair*) back up, baby, back up!

Speak Now (2010)

Favorite song: Back To December

My favorite on Speak Now may change over time because I haven’t yet listened to it as much as her later albums. I was tempted to pick the second track on the album, Sparks Fly, as it sounds more welcoming next to Back to December, which at first sounds a bit drippy. But that’s part of the appeal of Back to December – she paints the scene so well here with her choice of music and, of course, her lyrics. The first verse illustrates her growing ability to bring the mood of a story through life through her words.

Lyric highlight:

It turns out freedom ain’t nothing but missing you

Wishing I’d realized what I had when you were mine

Interesting versions: Of all her albums, I’d say that Speak Now is the one that would benefit most from a revamp for Taylor’s Version. This live version of Back to December merges into You’re Not Sorry, bridged by One Republic’s Apologize.

Red (2012)

Favorite song: All Too Well

What else?! Actually there are lots of great songs on Red to choose from – Treacherous is probably my second choice.

Lyric highlight:

Photo album on the counter, your cheeks were turning red

You used to be a little kid with glasses in a twin size bed

Interesting versions: Here’s Taylor performing the 10 minute version on SNL with her short film playing in the background. After releasing Folklore and Evermore in 2020, the 2021 release of Red (Taylor’s Version) and the extended All Too Well kept her in the spotlight throughout lockdown.

1989 (2014)

Favorite song: All You Had To Do Was Stay

1989 has a lot of big hits but rather than choosing one of the seven (!) singles, I’m going for All You Had To Do Was Stay. I’m choosing it as much, if not more, for the melody than the lyrics. The runner up was close: Out of the woods.

Lyric highlight:

Here you are now, calling me up, but I don’t know what to say
I’ve been picking up the pieces of the mess you made

Interesting versions: playing/singing it yourself! Here’s a live version but it would be nice to see an acoustic version.

Reputation (2017)

Favorite song: Call It What You Want

Reputation took some getting used to after I had spent lockdown listening to FolkloreRed, and Evermore. With many songs focusing on cadence and intonation over lyrics it seemed like a different world. I did stumble across her Delicate music video (who said research scientists don’t get out much?) and fell in love with it. However, I’m picking Call It What You Want as my top song from Reputation.

Lyric highlight:

And I know I make the same mistakes every time

Bridges burn, I never learn

At least I did one thing right, I did one thing right

Interesting versions: This live acoustic version on SNL:

Lover (2019)

Favorite song: Soon You’ll Get Better

I’m picking this song because it’s hard not to. Even for someone known for her emotion and openness, this song stands out. Soon You’ll Get Better is not the first time Taylor sung to her mother, but it’s the most poignant. It’s Nice To Have A Friend is also outstanding – it uses rhythm in a playful way, perhaps foreshadowing Closure from Evermore.

Lyric highlight:

Holy orange bottles

Each night I pray to you

Desperate people find faith

So now I pray to Jesus too

Interesting versions: This performance in April 2020 was the first time I noticed TS. Within a year she had become my favorite artist.

Folklore (2020)

Favorite song: Seven

My favorite song from Folklore has definitely shifted over time. I was first attracted to Exile, initially because of Justin Vernon who I was more familiar with than TS. I love Aaron Dessner’s guitar on Invisible String, which is also a sweet, whimsical song. But I’m picking Seven as my favorite song from perhaps the most important Taylor Swift album – the one that got us through one of the toughest years of our lives. Seven is all about childhood and it best represents Folklore’s wonderful innocence.

Lyric highlight:

Please picture me in the trees

I hit my peak at seven feet

In the swing over the creek

I was too scared to jump in

But I, I was high in the sky

With Pennsylvania under me

Interesting versions: The Long Pond Studio Sessions are a great way to experience Folklore.

Evermore (2020)

Favorite song: Right Where You Left Me

This album has grown on me more and more and I’d count several songs as general favorites – Marjorie and Evermore in particular. But I think the best song on the album is actually a bonus track: Right Where You Left Me. In time, I think it’ll be counted as one of her masterpieces.

Lyric highlight:

Matches burn after the other

Pages turn and stick to each other

Wages earned and lessons learned

But I, I’m right where you left me

Midnights (2022)

Favorite song: You’re On Your Own, Kid

As soon as I heard this song – even the first five seconds of it – I knew it would be a favorite. I immediately put it on repeat and told the rest of the album that it can wait until 2 am.

Lyric highlight:

Summer went away

Still the yearning stays

Agree or disagree with these choices? Comment below!

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