Out of the Woods and Into the Dumps: Taylor Swift's Albums Ranked From Saddest To Happiest

Taylor Swift’s discography makes us feel so many different ways. I’ve ranked her albums from saddest to happiest to try to make it easier for you to pick one that best matches your vibe for the day!

1. Folklore

This album is the absolute BEST when it comes to sad rainy days. Even the more lighthearted songs have relatively soft beats.

Saddest Song: “this is me trying”

This song is about doing your best and still not being enough. Lyrics like “They told me all of my cages were mental/ So I got wasted like all my potential” are so incredibly cry worthy.

Happiest Song: “invisible string”

Taylor talks about finding the person that the universe has been pushing her towards her entire life—the one person that made all of her past mistakes and obstacles worthwhile. Makes me kind of want a relationship… yikes!

2. Fearless

This album takes you through an entire relationship in a matter of 53 minutes. The songs reflect the thrill of the chase and the satisfaction of being in a relationship, but mostly it’s about the aftermath and heartbreak.

Saddest Song: “White Horse”

Taylor talks about losing faith in someone she once trusted. Lyrics like “ I’m not a princess, this ain’t a fairytale” reflect newfound maturity. Taylor was relatively young when this song came out, and there comes a point in all our lives when we realize life isn’t comparable to the fairytales we grew up watching. Which sucks.

Happiest Song: “The Best Day”

Taylor takes us through her childhood as she thanks her mom for being there for all of it. We all have someone in our lives we have to thank for who we’ve become and Taylor found a way to put it into words so we don’t have to!

3. Speak Now

The songs on this album are either incredibly heart-wrenching or serotonin inducing — there is literally no in-between.

Saddest Song: “Last Kiss”

Want a song that’ll make you miss the boyfriend you never had? This is it. Lyrics like “You told me you loved me/ So why did you go away?” and “You can plan for a change in the weather and time/ But I never planned on you changing your mind” are so emotionally charged. Literally just thinking about it makes me sad.

Happiest Song: “Mine”

This song talks about being in a relationship, overcoming obstacles and coming out stronger on the other side. Mega serotonin boost guaranteed!

4. Taylor Swift

This album is raw and incredibly relatable, especially when it comes down to young love—which is what most of us are going through, or hoping to go through, at this point in our lives.

Saddest Song: “Tied Together with a Smile”

Putting on a brave face for the world when you are feeling everything but has got to be one of the most difficult things — and this song encompasses that in the best way.

Happiest Song: “Mary’s Song”

This song is about growing up and falling in love with your childhood best friend. My question is (and this is me genuinely asking) does it get any cuter than that?

5. Red

phone with picture of taylor swift's red on the screen Photo by Omid Armin from Unsplash

Red is one of Taylor’s most mature albums. It deals with the deepest heartbreaks and feels like a stream of consciousness.

Saddest Song: “The Moment I Knew”

This song is loss, disappointment and heartache all in one. I sympathize so deeply with lyrics like “And what do you do when the one who means most to you/ Is the one who didn’t show?” to the point where I feel like I lived through it with her.

Happiest Song: “22”

There is no universe where someone hears this song and doesn’t immediately feel the need to jump up and dance. The song radiates so much joy and free spirit, it’s in my happy playlist!

6. 1989

If you want an album you can scream at the top of your lungs to while still keeping in touch with your deepest of feelings, this is it.

Saddest Song: “All You Had To Do Was Stay”

The heartbreaking lyrics in this song are masked by an upbeat tempo so that they don’t reveal themselves until you really pay attention to the words. “Why’d you have to go and lock me out when I let you in?” I fully didn’t notice how sad this track was until I googled the lyrics.

Happiest Song: “Shake It Off”

Okay, this song is the definition of the word care-free. I use this song when I need to hype myself up, especially that bridge — talk about power move!

7. Reputation

taylor swift repuatation album cover Photo by Raphael Lovaski from Unsplash

Reputation in one word: Badass! Even the sadder songs have killer beats that overshadow any tears that might emerge.

Saddest Song: “Dancing With Our Hands Tied”

Although I jump around to this song in my room, I just know if I heard an acoustic version I’d be in tears. I mean, “I, I loved you in spite of/ Deep fears that the world would divide us.” Like, come on.

Happiest Song: “Call It What You Want”

This song invalidates outside judgments. In a nutshell, it is basically saying, say what you want about me, I’m happy, that’s all that matters. Like girl, are you kidding? That’s all anyone wants to be able to say.

8. Lover

Lover is the ultimate serotonin booster. It’s finally finding your soulmate; it’s finally letting go of your past. It’s the end of a long journey to happiness.

Saddest Song: “Soon You’ll Get Better”

This song is such a great outlet for grief. Definitely not a song you listen to on any given day, but that just makes it that much sadder.

Happiest Song: “Paper Rings”

“I like shiny things, but I’d marry you with paper rings.” Need I say more?! It’s packed with so much desperation to be with the person you love, to the point that you don’t care for much else. Plus, who doesn’t love a good love story?

Want to see more HCFSU? Be sure to like us on Facebook and follow us on Instagram, Twitter, TikTok and Pinterest!