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Taylor Alison Swift never fails to brilliantly express the emotions of good times, bad times and everything in between. While I’ve adored every song she’s released (she’s incapable of making bad music), her newest album “Midnights” has forced me to think even deeper about which of her incredible songs have stuck with me the most throughout the years.

While you might not agree with every choice I made on this list, I can confidently say that each of these songs has been instrumental for one reason or another throughout my life.

“Cruel Summer”

Album: “Lover”

Ideal Time To Listen: When that summer fling becomes more than just a fling.

Best Lyrics:

“I don’t wanna keep secrets just to keep you.”

“the lakes” (Original Version)

Album: “Folklore”

Ideal Time To Listen: When you want to hear how much of a poetic genius Ms. Swift truly is.

Best Lyrics:

“What should be over burrowed under my skin.
In heart-stopping waves of hurt,
I’ve come too far to watch some name dropping sleaze
Tell me what are my words worth.”

“Would’ve, Could’ve, SHould’ve”

Album: “Midnights”

Ideal Time To Listen: Belt this one out in the car, trust me I’ve tried it.

Best Lyrics:

“God rest my soul, I miss who I used to be.
The tomb won’t close,
Stained glass windows in my mind.
I regret you all the time.”


Album: “Folklore”

Ideal Time To Listen: Obviously while wearing a cardigan.

Best Lyrics:

“You drew stars around my scars,
But now I’m bleedin’.”

“Holy Ground” (Taylor’s VersioN)

Album: “Red” (Taylor’s Version)

Ideal Time To Listen: When you’re happily reminiscing about the past.

Best Lyrics:

“Tonight I’m gonna dance,
For all that we’ve been through.
But I don’t wanna dance,
If I’m not dancing with you.”


Album: “Reputation”

Ideal Time To Listen: There is no correct answer because this is pop Swift at her finest. In my humble opinion, people should add “Getaway Car” to their party playlist.

Best Lyrics:

“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 win”


Album: “Evermore”

Ideal Time To Listen: When you need a good cry.

Best Lyrics:

“No one teaches you what to do
When a good man hurts you,
And you know you hurt him too.”


Album: “1989”

Ideal Time To Listen: Months after an impactful breakup and you start feeling yourself again.

Best Lyrics:

“Ten months sober, I must admit
Just because you’re clean, don’t mean you don’t miss it.
Ten months older, I won’t give in
Now that I’m clean, I’m never gonna risk it.”

“Dear John”

Album: “Speak Now”

Ideal Time To Listen: After becoming heartbroken over a boy with a “J” name.

Best Lyrics:

“And you’ll add my name to your long list of traitors who don’t understand,
And I’ll look back and regret how I ignored when they said ‘run as fast as you can.'”

“All Too Well” (Ten Minute Version) (Taylor’s Version) (From The Vault)

Album: “Red” (Taylor’s Version)

Ideal Time To Listen: Anytime. Anywhere. This is Taylor Swift’s masterpiece and my personal favorite song.

Best Lyrics:

“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.”

Thank you, Taylor, for these masterpieces. Happy listening!

I'm a junior at Penn State University studying Public Relations and minoring in English. I'm currently a writer for the life section!