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The Top 10 Saddest Love Songs Ever Recorded

Breaking up is the worst. Having to go through the torture of leaving (or being left) by someone is enough to make you want to lay on the sofa all day watching Gilmore Girls and wondering if Rory will ever find true love.

In the end, a little space and time can help you heal. But in the meantime, a big bowl of chocolate ice cream, some comfy PJs and a few really, really ridiculously sad songs are the perfect recipe to help as you wallow in your woe.

Luckily, we’re here to help! We’ve compiled our picks for the 10 saddest breakup songs ever written, including songs about lost love, songs about unrequited love and songs about heartbreak, to really get your emotions flowing.

Keep reading to find out what famous sad love songs made the cut!

10. Roy Orbison “Crying”

Released: 1962

One of the most recognized and saddest breakup songs, “Crying” gives you the chance to cry and lay in bed until the heartbreak passes. Add blankets and chocolate for best healing results.

“I thought that I was over you

But it’s true, so true

I love you even more than I did before

But, darling, what can I do?”

9. Johnny Cash “Hurt”


Released: 2002

How do you make a depressing song sadder? Have Johnny Cash sing it instead. By tweaking the melody and replacing the reverberating effects with acoustic instruments, Cash adds an element of sadness that only he can portray. The original song was released by Nine Inch Nails in 1994, but no one carries the story of heartbreak like Johnny Cash does.

“What have I become?

My sweetest friend

Everyone I know

Goes away in the end”

8. R.E.M. “Everybody Hurts”

Released: 1993

The end of a relationship can really, really hurt. R.E.M. embodies the loneliness and sadness with this slower track from Automatic for the People. Though it doesn’t necessarily mention love, “Everybody Hurts” understands how hard breakups can hit. Pull yourself out of your funk briefly with a good cry to this one.

“If you’re on your own in this life

The days and nights are long

When you think you’ve had too much of this life, hang on”

7. The Beatles “Yesterday”

Released: 1966

Sometimes, simple lyrics are all you need. Though the working title was “Scrambled Eggs”, Paul McCartney and John Lennon eventually rewrote the song to feature the story we now know. The guitar and violin duet lifts the lyrics to a more emotional state.

“Why she had to go?

I don’t know, she wouldn’t say

I said something wrong

Now I long for yesterday.”

6. The Cure “Pictures of You”

Released: 1989

This song instantly creates a montage of any moment. In this case, if you want to feel like the lead in a romantic comedy or John Hughes film as you reflect on your former relationship, this is that song. Indulge in the 80s fully with this iconic hit from The Cure.

If only I’d thought of the right words

I could have held on to your heart

If only I’d thought of the right words

I wouldn’t be breaking apart

All my pictures of you”

5. Joni Mitchell “Both Sides, Now”


In Love Actually, Emma Thompson says it best when she tells her husband, “Joni Mitchell is the woman who taught your cold English wife how to feel.” Even without the heart-wrenching feature of this song in the movie, Mitchell’s voice tells the story of disillusion and heartbreak through soaring vocals and masterful lyrics.

“I’ve looked at love from both sides now

From give and take and still somehow

It’s love’s illusions I recall

I really don’t know love at all”

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4. Harry Nilsson “Without You”

Released: 1972

Though the song was originally released by Badfinger, the quintessential breakup song was perfected by Harry Nilsson. The slower tempo and higher register vocals echo the pining sentiment of the song itself and make it one of the saddest breakup songs of all time.

“No, I can’t forget tomorrow

When I think of all my sorrow

When I had you there, but then I let you go”

3. Phil Collins “I Wish It Would Rain Down”

Released: 1989

With one of the weirdest videos on the list, “I Wish It Would Rain Down” borrows from The Temptations but adds that 80s power ballad vibe we all love so well. Collins abandons the upbeat usual music for a sadder story of unrequited love. Bonus: the video shows us what the world might be like if Phil Collins went by Bill instead.

“Cause I know, I know I never meant to cause you no pain

And I realize I let you down

But I know in my heart of heart of hearts

I know I’m never gonna hold you again”

2. Bonnie Raitt “I Can’t Make You Love Me”

Released: 1991

Sometimes it’s worth it to try again. But Bonnie Raitt knows better; she captured the essence of a loveless relationship in this ballad from the 90s. The words hit close to home, and the soft vocals contribute to the feeling of an unbalanced relationship. If you’re looking for lost love songs that will tell it to your straight, this is definitely one to listen to.

‘Cause I can’t make you love me if you don’t

You can’t make your heart feel something that it won’t

Here in the dark, in these final hours

I will lay down my heart and I’ll feel the power

But you won’t, no you won’t

‘Cause I can’t make you love me, if you don’t

1. Joy Division “Love Will Tear Us Apart”

Released: 1980

Sorry, Morrissey. Joy Division was one of the first to bring emotion and tempo together with this hit from 1980. Their band would go on to inspire The Cure, The Smiths, and many others in the world of alternative music, and this song made it okay to cry and dance at the same time.

“Why is the bedroom so cold?

You’ve turned away on your side.

Is my timing that flawed?

Our respect runs so dry.

Yet there’s still this appeal

That we’ve kept through our lives”

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