The Saddest Sad Songs

Cry it out. You know you want to.

If you really hate lists of things recommended by some random person on the internet, you are absolutely welcome — encouraged even! — to stop reading right now. I normally hate these things, too. Having said that, I’m sharing my favorite, saddest songs anyway (thanks to this little piece on Jezebel for inspiration). When you’re heart-broken, I urge you to cry it out. Listen to sad songs. Stay in your bed for a day. Or two. Wear your most comfortable pajamas. Wallow in your own self-pity. Mope and feel sad and cry and eat ice cream and order take-out sushi and drink wine alone in your kitchen. Do this. Feel your feelings. And then move on when you’re ready.

Now, in no particular order, my favorite, saddest, sad songs:

— 1 —
“Almost Lover” by A Fine Frenzy

The saddest sad song for crying it out over unrequited love — the most unfair, soul-crushing love of all. Spending time with the person you love, who just doesn’t feel quite the same about you, is like a bad habit you just can’t break — it feels oh-so-good in the moment even though you know you’ll regret it when it’s over. This is the glutton-for-punishment kind of love.

Most heart-wrenching lyrics:

I should’ve known you’d bring me heartache
Almost lovers always do

I cannot go to the ocean
I cannot drive the streets at night
I cannot wake up in the morning
Without you on my mind
So you’re gone and I’m haunted
And I bet you are just fine
Did I make it that easy
To walk right in and out of my life?

— 2—
“Love Me Like I’m Not Made Of Stone” by Lykke Li

The saddest sad song for when you’re craving a tiny bit of something that makes you feel warm and tingly instead of cold and heart-broken.

Most heart-wrenching lyrics:

A devil’s hand across my heart
As we dance through the dark
So go ahead, go ahead
Love me deep, until you can’t

Even though it hurts, even though it scars
Love me when it storms, love me when I fall
Every time it breaks, every time its torn
Love me like I’m not made of stone
Love me like I’m not made of stone

— 3—
“Ghost” by Ingrid Michaelson

The saddest sad song for when that relationship you so very much wanted to work is failing miserably and you die a little bit every moment as it comes crashing down on you.

Most heart-wrenching lyrics:

Do you remember when the walls fell
Do you remember the sound that the door made when you closed it on me
Do you know that I went down to the ground
Landed on both my broken-hearted knees

I didn’t even cry
‘Cause pieces of me had already died

I’m a ghost
Haunting these halls
Climbing up walls that I never knew were there
And I’m lost
Broken down the middle of my heart, heart

— 4 —
“Jealous” by Labrinth

The saddest sad song for when you’re no longer the one-and-only to that one person you thought would be your one-and-only.

Most heart-wrenching lyrics:

I wished you the best of
All this world could give
And I told you when you left me
There’s nothing to forgive
But I always thought you’d come back, tell me all you found was
Heartbreak and misery
It’s hard for me to say, I’m jealous of the way
You’re happy without me

— 5 —
“Never Had” by Oscar Isaac

The saddest sad song for all the same reasons as number 1: an almost-lover, an unrequited love, the one you never had.

Most heart-wrenching lyrics:

You came close enough to know my heart beat but
Still not close enough for me

Through the good times and the bad
You were the best I never had
The only chance I wish I had to take
There was no writing on the wall
No warning signs to follow
I know now and I just can’t forget
You’re the best I never had

— 6 —
“Nicest Thing” by Kate Nash

The saddest sad song for all the same reasons as number 1: an almost-lover, an unrequited love, the nicest thing you almost had. Notice a theme here?

Most heart-wrenching lyrics (the whole damn song, really):

I wish you had a favorite beauty spot
That you loved secretly
‘Cause it was on a hidden bit
That nobody else could see
Basically, I wish that you loved me
I wish that you needed me
I wish that you knew when I said two sugars,
Actually I meant three

I wish that without me your heart would break
I wish that without me you’d be spending the rest of your nights awake
I wish that without me you couldn’t eat
I wish I was the last thing on your mind before you went to sleep

Look, all I know is that you’re the nicest thing I’ve ever seen
And I wish that we could see if we could be something

— 7—
“Stay” by Rihanna featuring Mikky Ekko

The saddest sad song for every heartbreak and heartache — unrequited love, love that left or got away, love that didn’t work out, and love that simultaneously fills a void while creating one. When, for better or worse, you really just wish that person stayed. Just a little longer. There are many situations in which this song may apply — and they’re all sad.

Most heart-wrenching lyrics:

Not really sure how to feel about it.
Something in the way you move
Makes me feel like I can’t live without you.
It takes me all the way.
I want you to stay.

Ooh, ooh, ooh, the reason I hold on
Ooh, ooh, ooh, ‘cause I need this hole gone
Funny you’re the broken one but I’m the only one who needed saving
‘Cause when you never see the light it’s hard to know which one of us is caving.

— 8 —
“Temptation” by Moby

The saddest sad song for when you need to say goodbye (“oh it’s the last time”) to somebody you really don’t want to have to say goodbye to (“I’ve never met anyone quite like you before”) and yet somehow find solace within yourself (“Tonight I think I’ll walk alone”). Maybe this is about your secret lover. Maybe this is about your temporary lover. Whoever it’s about, they’re incredible, and then they’re gone.

Most heart-wrenching lyrics:

Oh it’s the last time; Oh it’s the last time

And I’ve never met anyone quite like you before
And I’ve never met anyone quite like you before

And I’ve never met anyone quite like you before
Oh, up, down, turn around; please don’t let me hit the ground
Tonight I think I’ll walk alone; find my soul as I go home

— 9 —
“Rest of My Life” by Rilo Kiley

The saddest sad song for the one who got away. This one’s pretty self explanatory, but the simple frankness and melody of this song really conveys the overwhelming hurt.

Most heart-wrenching lyrics:

Just your smile
Leaves me satisfied
Though you’re not mine

So for the rest of my life
I’m gonna search for someone just like you

Honorable mentions:

Other songs that might be sad, or maybe they just sound sad, or maybe they just make me feel sad:

• “Dorian” by Agnes Obel
• “We’re All Going to Hell” by Ida Maria
• “Be Good” by Waxahatchee
• “Blue Leaves” by Soley
• “For You” by Angus & Julia Stone
• “Jar of Hearts” by Christina Perri
• “Love Love Love” by Of Monsters and Men
• “Fake Plastic Trees” by Radiohead
• “Luna” by Zoé
• “Michigan” by The Milk Carton Kids

That’s quite a few sad songs to get you feeling your feelings. I could always use new sad songs (unfortunately), so write a response if you’d like to share your favorites with me.

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