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Top 10 Sad Break-Up Songs

Because sometimes a break up will fill you with tears instead of rage

Top 10 Sad Break-Up Songs is a follow up to my previous, significantly more Angry List. I know I said I liked being a horrendously bitter, grudge-holding individual, but that doesn’t mean I don’t have sad feelings (only sometimes, very rarely). This is the soundtrack to my sadness. Cue the uncontrollable sobbing in 3… 2… 1!

1. Frank Ocean – “Miss You”

I miss you, like everyday
Wanna be with you, but you’re away
I said I miss you, missing you insane
If I got with you, would it feel the same?

Frank Ocean co-wrote this song for Beyonce’s latest album, titled 4. As much as I love Beyonce, Frank’s performance shown above is my personal favorite version of “Miss You”. There’s just something about a live, slowed down version set to piano that just hits me right in the gut.

2. Adele – “Someone Like You”

I heard that you’re settled down
That you found a girl and you’re married now
I heard that your dreams came true
Guess she gave you things I didn’t give to you.

Well, this was an obvious choice. Crooning your way through heart-rendering music is always a therapeutic move, but none are quite as therapeutic as this one. There’s a reason why that one SNL skit showcased “Someone Like You” as the perfect ugly crying song. Like they said, everyone with a heart and an iTunes account does it, so you might as well join in.

3. Mac Lethal – “inohowutheenk”

See I know what you’re thinking
You’re hoping I’m coming home to soak in potions with you
Like in the living room the ocean is blue
And this ain’t carpet, no, it’s warm sand
This is paradise where we never scream and never make a door slam.

Words cannot describe how I feel about this song. I’ve laid in bed in the dark listening to this on repeat while weeping into mugs of tea and/or vodka. Mostly vodka. (Don’t look at me like that, this is totally normal behavior.)

Seriously, though, the main reason why I feel so drawn to “inohowutheenk” has to do with the simplicity and honesty of the lyrics and the dreaminess of the backing track. When he talks about closing his eyes and imagining paradise with his ex-lover… yeah, I know that feeling.

4. Lauryn Hill featuring Mary J. Blige – “I Used To Love Him”

I chose a road of passion and pain
Sacrificed too much and waited in vain
Gave up my power ceased being a queen
Addicted to love like the drug of a fiend

These lyrics are absolute poetry. It’s a pretty sad song, but ultimately a very empowering and motivational one about realizing you deserve better, and moving on from a relationship that only caused you pain.

5. Susanna and the Magical Orchestra – “Love Will Tear Us Apart”

When routine bites hard, and ambitions are low
And resentment rides high, but emotions won’t grow
And we’re changing our ways, taking different roads
Love, love will tear us apart again.

Here’s another fantastic cover on my list, this time of Joy Division’s much-loved classic song. Susanna’s echoey vocals on this track add an ethereal note to an already sad song about the emotional distance felt between lovers. Plus, I can’t think of a line much sadder than “love will tear us apart, again.”

6. Bruno Mars – “When I Was Your Man”

Hmmm too young, too dumb to realize
That I should have bought you flowers and held your hand
Should have gave you all my hours when I had the chance
Take you to every party cause all you wanted to do was dance
Now my baby’s dancing, but she’s dancing with another man.

I have a bit of a love/hate relationship with Bruno Mars’ music (he’s just not really my thing) but I can appreciate this song as the break-up ballad that it is. In it, a guy mourns the loss of his relationship with the girl he’s singing about, because his pride, his ego, his needs and his selfish ways caused a good strong woman like her to walk out of his life.

7. Daughter – “Youth”

And if you’re in love, then you are the lucky one
‘Cause most of us are bitter over someone
Setting fire to our insides for fun
To distract our hearts from ever missing them
But I’m forever missing him.

This intensely beautiful song never fails to bring me to tears any time I sing along with it. The hopelessness in the words and in her voice make it a necessary addition to a list of Sad Break-Up Songs.

8. Bill Withers – “Ain’t No Sunshine When She’s Gone”

Ain’t no sunshine when she’s gone
It’s not warm when she’s away
Ain’t no sunshine when she’s gone, and she’s always gone too long
Anytime she goes away

This song has gotten covered a lot since it came out in the 1970′s (for good reason, because it is downright amazing) but I’m just so in love with the original. Honestly, just listen to those vocals and watch that performance; it’s so damn good. Describing your beloved as the sun in your life is a pretty devotional and meaningful thing to say, so what happens when that light leaves you?

I dunno, man. I prescribe more ugly crying.

9. Bon Iver – “Skinny Love”

Come on, skinny love, just last the year
Pour a little salt, we were never here
Staring at the sink of blood and crushed veneer.

This song is for those moments when you just know the relationship is going to end, but you hang on by the skin of your teeth hoping that something would change and that you guys can still fix it. And sometimes you can, but other times…

Justin Vernon of Bon Iver describes it best in this quote from an interview: “You’re in a relationship because you need help, but that’s not necessarily why you should be in a relationship. And that’s skinny. It doesn’t have weight. Skinny love doesn’t have a chance because it’s not nourished.”

10. J. Cole – “Nothing Lasts Forever”

We gave it up, but some days I be wakin’ up and wantin’ one more
But what for? Maybe it’s just the weather
We break each other’s hearts, so maybe it’s for the better
Holler whenever, cause you always got a friend in me
And nothing lasts forever, least we got these memories.

Semi-amiable, mutual breakups are probably one of the hardest just because you don’t even have the luxury of intense undying hatred to hold onto once everything’s over. J. Cole’s song cycles through all the different emotions and states of mind someone might go through post break-up, including bitterness, nostalgia, anger, yearning, and confusion. Listening to this one can be a good way to try and work all of that mess out.

Did my list accidentally leave out a heart-wrenching break-up song? Let me know with a comment below! 

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Categories: Music

Author:Christine Duong

Christine is a balut-crunching, MMO-playing, hip hop-loving, Monster®-chugging burst of energy. You can find her at Pop Insomniacs. Follow her on Twitter @praytochristine.

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17 Comments on “Top 10 Sad Break-Up Songs”

  1. June 2, 2013 at 12:33 PM #

    How about Taylor Swift “We are never getting back together”
    http://vevo.ly/Nz97Vq

  2. MJ
    July 1, 2013 at 9:22 PM #

    You Lost Me-Christina Aguilerá
    Jar Of Hearts-Christina Perry
    Broken-Hearted Girl – Beyoncé
    Wake Up Alone-Amy Winehouse
    Dreams To Remember–Otis Reddding

  3. Lou
    August 6, 2013 at 12:02 PM #

    Ray Lamontage’s song Burn very heart wrenching

  4. Jermaine
    August 8, 2013 at 11:47 AM #

    Add “Boomerang” by Jay Montra it’s definitely top 5 of 2013

    https://soundcloud.com/jaymontra/boomerang

  5. James Bobin
    August 13, 2013 at 4:54 AM #

    What about “The Winner Takes It All’ by ABBA?

  6. Sakshi parihar
    August 22, 2013 at 8:28 AM #

    Plz come back i realy miss u

  7. Aje vasava
    October 9, 2013 at 5:35 PM #

    I realy miss u URI

    • Aubrey Rayleen Gibson
      October 28, 2013 at 9:44 PM #

      Who is URI?

  8. Kayla
    November 2, 2013 at 3:51 PM #

    You lost me – Christina Aguelara

  9. Jenny
    November 6, 2013 at 4:32 AM #

    Miley Cyrus – Wrecking Ball…
    California liar – Not over you

  10. andrea
    November 9, 2013 at 7:35 AM #

    Rascal Flats “What Hurts The Most”

  11. Balawankit
    December 10, 2013 at 8:42 AM #

    A Thousand Years by Christina Perri definitely one of the best

  12. January 4, 2014 at 11:24 AM #

    say something- Christina Aguilera

  13. Sparxxx
    March 7, 2014 at 9:45 PM #

    Cat Power – Good Woman

  14. TomP
    March 18, 2014 at 10:41 AM #

    … My 25 sad songs, which I really love … http://www.youtube.com/watch?v=OQFtqLxp2nY

Trackbacks/Pingbacks

  1. Walk Away | Rooftop Rendezvous - June 14, 2013

    […] Top 10 Sad Break-Up Songs (popinsomniacs.com) […]

  2. Top 10 “Good Vibes” Break-Up Songs | Pop Insomniacs - October 17, 2013

    […] song could have easily gone on our Top 10 Sad Break-Up Songs post. Either way, it’s an incredibly beautiful song that can be interpreted a number of […]

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