The release of Taylor Swift’s surprise new album, Midnights, is the talk of the town, and it’s really gotten me thinking about how Taylor-heavy my playlists have been lately. Her albums give such a range of songs for all feelings and occasions, and she has this incredible power of putting emotions perfectly into lyrics. Today, I want to share nine of my favorite Taylor Swift songs that spin raw sadness and pain into beautiful pieces of art. An important note: I’m currently deep in my folklore era, so you’ll notice that the album is featured quite a bit on the list. This is not an apology, but a fair warning that no folklore slander is tolerated on this page xoxo. Let’s jump in:
- “All Too Well (10 Minute Version) (Taylor’s Version),” Red (Taylor’s Version)
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Of course, I had to start off my list with this beauty. Since the Red (Taylor’s Version) era will be brought to a close with the release of Midnights, I’ve been thinking about how much this song has meant to me in the past 11 months since its release. In its lyrics, Taylor manages to put words to some unspeakable pain about haunting heartbreak. You know, the kind of heartbreak that leaves such a bad taste in your mouth that even when you want to miss the person, you’re reminded of the awful things they’ve done to you and you’re broken all over again. Lyrics like, “And I was thinking on the drive down / Any time now, he’s gonna say it’s love / You never called it what it was” really resonates with those “we were never on the same page” type of relationships. When she released this special extended version, I was feeling all the pain she writes about here, which made the song feel like the perfect twist of the knife. Even though I’m in a much better place in my life now, I will never not sob as soon as I hear that echoey, heart-wrenching intro.
- “Clean,” 1989
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This song hurts because it’s accurate. With “Clean,” Taylor has written an honest healing story; there are highs, lows, and relapses. My favorite line is, “You’re still all over me / Like a wine-stained dress I can’t wear anymore.” Some relationships leave you feeling ruined, like you’ll never be the same. This song reminds us that sometimes, letting the heartbreak wash over us allows us to finally feel clean and free from the pain.
- “Look What You Made Me Do,” reputation
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This one might be a surprising addition to the list. It made the cut due to a personal memory that sticks out in my head: about a year ago, I was healing from a breakup that had left me reeling. As I walked to work with this song playing in my earbuds, I felt my sadness turn to anger for the first time. I started crying angry tears because I realized that with the end of the relationship, I had finally gotten my power back. When Taylor wrote reputation, she was angry. This is a villain arc album, and I think “Look What You Made Me Do” is a great song for validating heartbreak anger.
- “Afterglow,” Lover
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In “Afterglow,” Taylor manages to capture exactly what it feels like to self-sabotage (a sensation I’m all too familiar with). Sometimes, when a past relationship leaves you so battered and bruised, you carry that pain (and fear) into a new connection. Taylor writes, “I blew things out of proportion, now you’re blue / Put you in jail for something you didn’t do / I pinned your hands behind your back, oh / Thought I had reason to attack, but no.” She describes that moment when you realize (just in time) that you’re bleeding from old wounds onto a new person. It makes me cry happy tears because it helps me realize how safe I feel in my current relationship, and how different it feels from the pain of my past.
- “cardigan,” folklore
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“You drew stars around my scars / But now I’m bleeding.” With two lines, Taylor captures what it’s like to share your painful past with someone, and then watch them become a new part of that pain. Ouch.
- “mirrorball,” folklore
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You know I had to include the people-pleaser anthem. If you’ve ever felt like you would change everything about yourself to be liked by others, you just might be a mirrorball. “I’m still a believer but I don’t know why / I’ve never been a natural / All I do is try, try, try / I’m still on that trapeze / I’m still trying everything / To keep you looking at me.” If you need me, I’ll be crying under my covers for the next three to five business days. Fellow mirrorballs are welcome.
- “mad woman,” folklore
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This song is a masterpiece. I will not be taking arguments, comments, or criticisms at this time. Once again, Taylor gives us a beautiful melody that doubles as a social commentary: “And you’ll poke that bear till her claws come out / And you find something to wrap your noose around / And there’s nothing like a mad woman.” The world will really tear a woman down, bash her physical appearance, dismiss her achievements, mute her voice, degrade her in the street, and then use her resulting anger as a reason to villainize her. I highly recommend listening to this song if you’ve ever felt like your anger has been minimized or dismissed. It’s honestly so validating.
Republic Records - “gold rush,” evermore
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This song sounds like a musical version of one of my classic overthinking spirals. Taylor writes, “I don’t like that anyone would die to feel your touch / Everybody wants you / Everybody wonders what it would be like to love you” and suddenly I realize that I’m not the only one who’s ever worried about my partner being pursued by other people. Insecurity? Yes. A legitimate fear? Absolutely, especially if a past partner showed you that they couldn’t be trusted. This song helps me grapple with feelings that I still can’t even vocalize.
- “tolerate it,” evermore
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Ever felt taken for granted in a relationship? This one’s for you. Taylor sings, “I know my love should be celebrated / But you tolerate it” in a quiet voice as if she can’t hear me sobbing. If you’ve ever felt like you’ve given someone your all while they’ve given you nothing, this song puts the pain into words.
There you have it. If you ever need a good cry, or even just need help coming to terms with some feelings of heartbreak, these songs will never fail you. If you need me, I’ll be tearfully enjoying a pint of dairy-free ice cream and listening to “mirrorball” on repeat.
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