Top 10 Saddest Taylor Swift Songs

Taylor's incredible storytelling and raw emotion have produced some truly heart-wrenching tracks throughout her career.

With your help, we've compiled the ultimate list of Taylor's saddest songs, a collection of melodies that explore heartbreak, loss, regret, and the complexities of human emotion.

Whether you're going through a tough time or simply want to appreciate Taylor's lyrical genius, this list is sure to have something that speaks to your soul.
The Top Ten
1 Ronan

Death sucks, full time, and it sucks even more if it's the death of a young child. After learning about "Rockstar Ronan"----a four-year-old boy who lost the battle to cancer---Taylor proceeded to do what she does best----write a song about it and leave us all sobbing. Thanks for all of those late-night sobbing sessions, Taylor.

About a boy who had cancer. I know Taylor is selfless, but making a song about a boy who had cancer will make you cry.

I can't here this song without crying. I have a little sister and, although she's thirteen, I'm scared to death she'll get cancer and die

2 The Archer

The Archer is like mirrorball in the way that it also shows how insecurities can physically break you, and then nobody can help you, or even tries to, unless they gain something from it. "I've been the archer, I've been the prey. Who could ever leave me, darling, but who could stay?"

3 Soon You'll Get Better

Cancer is an awful thing, especially if it happens to someone very close to you---in Taylor's case, her mother, Andrea. Taylor and Andrea have a very close bond ("But who am I supposed to talk to? What am I supposed to do if there's no you?") and losing her is something that Taylor is DEFINITELY never going to be ready for. The way she sings the song like she's trying not to cry makes it even more sad. Double whammy if you remember that Taylor's grandmother, Marjorie (see number 8) had died barely 12 years before.

4 Never Grow Up
5 This is Me Trying
6 A Place In This World
7 Safe & Sound

I love this song it makes me feel sad though but it's good to sing a lot well at least I do!

Saddest song ever but if you listen closely you can find happiness in it

Safe and sound is relaxing and peaceful. Not THAT sad, but a little

8 Back to December
9 The Best Day

Yeah, sure, totally, a song called "The Best Day" is definitely a sad song. Really, who put this on here?

10 Mirrorball

Anybody who's a "pathological people-pleaser" understands how hard it is to break yourself into a million pieces in order to make others happy. A mirrorball seems happy and bouncy and shiny----until it falls, shatters, and nobody even bothers to put it back together. Taylor Swift perfectly conveys this with lines like "drunk as they watch my shattered edges glisten" and "I can change everything about me to fit in."

The Newcomers

? loml
The Contenders
11 Teardrops On My Guitar
12 Dear John

Both Dear John and Back to December has a very personal, emotional meaning to me.
Still voting for Dear John, because the tune is sadder.

13 Tied Together With a Smile
14 Fifteen
15 You're Losing Me

This song is basically overflowing with all kinds of euphemisms. "I'm getting tired even for a phoenix---always rising from the ashes, mending all her gashes, you might just have dealt the final blow," and "My face was gray, but you wouldn't admit that we were sick," and "And all I did was bleed as I tried to be your bravest soldier." The relationship Taylor sings about hurt her in many ways, and this song is basically her begging the person who hurt her to notice that she's not okay. "Stop, you're losing me," indeed.

16 Cold As You
17 All Too Well
18 Last Kiss

You gotta admit this song is pretty sad

19 White Horse

This song is really sad, I almost started crying.

20 The Moment I Knew

This song tells about her story with jake gyllenhall when he left her alone at her st bithday party, this song always makes me cry

21 Clean
22 Champagne Problems
23 Haunted

The music of Haunted has a dark, almost panicked sound to it, and that joined with lyrics like "Come on, come on, don't leave me like this, I thought I had you figured out" make it sound like Taylor is basically begging somebody not to leave her, to help her understand---"Something's gone terribly wrong you're all I wanted..." It's dark, to say the least.

24 Marjorie

Losing a grandparent is always hard, no matter how you lose them. Marjorie Finlay died of unknown causes, and Taylor feels like she didn't get to know her enough ("I should've asked you questions, I should've asked you how to be") before her time was up. At least Taylor has fond memories of her grandmother, which make the song both sad and oddly hopeful.

25 A Perfectly Good Heart
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