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 is devastating, especially when it involves 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 those late-night crying sessions, Taylor.

This song is 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 hear 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 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 sadder. It's a double whammy if you remember that Taylor's grandmother, Marjorie (see number 8), died barely 12 years before.

3 The Archer

"The Archer" is like "Mirrorball" in the way it also shows how insecurities can physically break you. 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?"

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.

8 Back to December
9 The Best Day
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, 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 Contenders
11 Teardrops On My Guitar
12 Last Kiss

You have to admit this song is pretty sad.

13 Dear John

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

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

This song is overflowing with 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."

"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.

17 Cold As You
18 All Too Well
19 White Horse

This song is really sad. I almost started crying.

20 The Moment I Knew

This song tells the story of her relationship with Jake Gyllenhaal when he left her alone at her birthday 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," makes 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 You Belong With Me
25 Shake It Off
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