29 Breakup Songs Guaranteed To Make You Ugly Cry

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girl holding a record

Because sometimes that's just what you need.

Break ups are hard to get through, a given indeed.

While music can almost always help you get through the tough times that follow, there's some music that's so deep and so relatable that it can actually make you rel-ive shit you had hoped you'd blocked out.

Even worse are the songs that put you in the artist's shoes without never even experiencing anything the lyrics talk about.

This tends to happen to me every time I listen to the Waiting to Exhale soundtrack — the words force me to become a middle-age mother of two, whose husband left her after 13 years and that's word to everything.

I'm still in my early 20s — what do I know about that kind of heartache and that kind of strength?

What I do know is about is the great mood-altering impact of music.

That said, here are 29 of the saddest of the sad break up songs ever recorded, songs that are likely to reduce you to tears whenever or whatever or wherever you listen to them.


(You should know it was extremely difficult for me to not list every song from 90s r&b).
1. Why Does It Hurt So Bad by Whitney Houston
My life's been better
Since the day I left you boy
I must admit life's been kind to me
I went and did the things I said I would boy
I found someone who loves me for me
Haven't had much drama since the day that we split boy
My heart's never been more at ease
And when I think of all the things you put me through
Leaving you has been the best thing for me

So why does it hurt so bad
Why do I feel so sad
I thought I was over you
But I keep crying
When I don't love you
So why does it hurt so bad
Baby I thought I had let you go.

This classic Whitney song perfectly sums up the confusion that comes along with ending a relationship that you knew was headed for a dead end from the very start. The good lovin' or his charm is what kept you there longer than you need. Yet after the breakup you can't help but miss him. It's an inevitable emotion in any case, but slightly more confusing in these instances. 

2. When I Was Your Man by Bruno Mars

My pride, my ego, my needs, and my selfish ways
Caused a good strong woman like you to walk out my life
Now I never, never get to clean up the mess I made, oh
And it haunts me every time I close my eyes

It all just sounds like ooh, ooh ooh ooh ooh
Mm, 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

A song filled with regret and so much love — we only hope to find this kind of man someday — the type of man who learns from his past mistakes and wants only the best for you.
3. Rolling in the Deep by Adele

The scars of your love remind me of us
They keep me thinking that we almost had it all
The scars of your love, they leave me breathless
I can't help feeling

We could have had it all
(You're gonna wish you never had met me)
Rolling in the deep
(Tears are gonna fall, rolling in the deep)
You had my heart inside of your hand
(You're gonna wish you never had met me)
And you played it to the beat

Adele is the queen of heartbreak jams, and it's because her soulful words have so much power forcing you to recall the "scars" of your own love. 
4. It Will Rain by Bruno Mars
If you ever leave me baby,
Leave some morphine at my door
'Cause it would take a whole lot of medication
To realize what we used to have,
We don't have it anymore.
There's no religion that could save me
No matter how long my knees are on the floor
Ooh so keep in mind all the sacrifices I'm makin'
Will keep you by my side
Will keep you from walkin' out the door.

Before Bruno Mars was cranking out disco hits, it was his slightly suicidal yet super-relatable love ballads that won us over. Heartbreak does leave you feeling like you're near death. I just don't know if I'd be ready to end it all for an f*ckboy (yes, we're generalizing), but the songs of his past albums still resonate to the core (somehow).

5. End of the Road by Boys II Men

Why do you play with my heart?
Why do you play with my mind?

Said we'd be forever
Said it'd never die
How could you love me and leave me and never
Say goodbye?

When I can't sleep at night
Without holding you tight
Girl, each time I try I just break down and cry
Pain in my head
Oh, I'd rather be dead
Spinning around and around

This song marked a period in time when love meant something, and even when people (read: men) f*cked up they didn't have too much pride to beg you. Well, at least not the men of Boys II Men.

6. Breakeven by The Script  

I'm still alive but I'm barely breathing
Just prayin' to a god that I don't believe in
'Cause I got time while she got freedom
'Cause when a heart breaks no it don't break even

Her best days will be some of my worst
She finally met a man that's gonna put her first
While I'm wide awake she's no trouble sleeping
'Cause when a heart breaks no it don't break even, even, no

There's nothing more difficult than experiencing heartache while the other person goes on with life as if it were nothing, and this song does a perfect job at conveying how it feels as you try not to watch to hard as they move on with their life while you struggle to break free of the pain.
7. What Hurts the Most by Rascal Flatts

I can take the rain on the roof of this empty house
That don't bother me
I can take a few tears now and then and just let 'em out
I'm not afraid to cry every once in a while
Even though goin' on with you gone still upsets me
There are days every now and again I pretend I'm okay
But that's not what gets me

What hurts the most was being so close
And havin' so much to say
And watchin' you walk away
And never knowin' what could've been
And not seein' that lovin' you
Is what I was trying to do

Some days it can feel difficult to pretend everything is okay when really you're dying on the inside for closure. 

8. Emotions by Destiny's Child

In the words of a broken heart
It's just emotion taken me over
Caught up in sorrow, lost in my soul
But if you don't come back
Come home to me, darling
Don't you know there's nobody left in this world
To hold me tight
Don't cha know there's nobody left in this world kiss goodnight
Goodnight, goodnight, goodnight

I'm there at your side,
I'm part of all the things you are
And you've got a part of someone else
You've gotta go find your shining star

And where are you now, now that I need you?
Tears on my pillow wherever you go
Cry me a river that leads to your ocean
You never see me fall apart

Never forget that Destiny's Child was life and not just for their dance hits, but for their lovey-dovey lyrics too. This one, in particular, is all about the emotional rollercoaster we've been on at one point or another.

9. What's Left of Me by Nick Lachey

Now I'm broken
And I'm fading
I'm half the man I thought I would be
But you can have
What's left of me

I've been dying inside
Little by little
Nowhere to go
But goin' out of my mind
In endless circles
Runnin' from myself until
You gave me a reason for standing still

And I want you
And I feel you
Crawling underneath my skin

This song was apparently written in reference to he and Jessica Simpson's divorce and although Nick doesn't quite admit that, the proof is in the pudding.

10. Everytime by Britney Spears

I may have made it rain
Please forgive me
My weakness caused you pain
And this song's my sorry

At night I pray
That soon your face will fade away

Every time I try to fly I fall
Without my wings
I feel so small
I guess I need you baby 
And every time I see
You in my dreams
I see your face
You're haunting me
I guess I need you baby

One of Britney's few ballads, it's often said that this was her response to ex-boyfriend Justin Timberlake's Cry Me a River. And, if it truly is: How could he not forgive that?

11. Wrecking Ball by Miley Cyrus
Don’t you ever say I just walked away
I will always want you
I can’t live a lie, running for my life
I will always want you
I came in like a wrecking ball
I never hit so hard in love
All I wanted was to break your walls
All you ever did was break me
Yeah, you wreck me
Right before the storm that became Miley, she gave us this calm and loveable piece of work. This song is all the proof you need that loving someone who is emotionally unavailable is risky business.
12. Gone by 'NSync

I don't wanna make excuses, baby
Won't change the fact that you're gone
But if there's something that I could do
Won't you please let me know?
The time is passing so slowly now
Guess that's my life without you
and maybe I could change my every day
But baby I don't want to

So I'll just hang around
and find some things to do
To take my mind off missing you
and I know in my heart
You can't say that you don't love me too
Please say you do

Ever felt desperate to keep the ground from under you crumbling? To keep the person you love deeply by any means? Well, that's what our fave boyband 'NSync is talking about.
13. Over My Head by The Fray
And suddenly I become a part of your past
I'm becoming the part that don't last
I'm losing you and its effortless
Without a sound we lose sight of the ground
In the throw around
Never thought that you wanted to bring it down
I won't let it go down till we torch it ourselves
Everyone knows I'm in
Over my head
Over my head
With eight seconds left in overtime
She's on your mind
She's on your mind
For any and everybody who refuses to let go without a fight ... this song is for you. Hang in there. 
14. Stay by Rihanna featuring Mikky Ekko
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
It's not much of a life you're living
It's not just something you take it's given
Round and around and around and around we go
Oh now, tell me now, tell me now, tell me now you know
Early on in the breakup it's , eally hard to imagine life without this person. Once upon a time you were able to do it but none of that matters now.
15. Somebody That I Used I Know by Gotye

Now and then I think of when we were together
Like when you said you felt so happy you could die
Told myself that you were right for me
But felt so lonely in your company
But that was love and it's an ache I still remember

You can get addicted to a certain kind of sadness
Like resignation to the end, always the end
So when we found that we could not make sense
Well you said that we would still be friends
But I'll admit that I was glad that it was over

When the person you thought you knew best becomes a complete stranger, when it's all said and done, you find a way to be relieved despite your obvious state of love sickness. Weird how that works, huh?
16. Let It Flow by Toni Braxton

Don't nobody want no broke heart
And don't nobody want no two time losers
Ain't nobody gonna love you like you are
If you take whatever he brings your way

You see the thing of it is we deserve respect
But we can't demand respect without change
There comes a time when we must go our own way

Just let go
Let it flow, let it flow, let it flow
Everything's gonna work out right, you know
Just let go, let it flow, let it flow, let it flow
Just let it go

Moving on is easier said than done, but once you do there's better things ahead. And we have Toni Braxton to thank for helping us realize this. 

17. Back to Black by Amy Winehouse

He left no time to regret
Kept his dick wet
With his same old safe bet
Me and my head high
And my tears dry
Get on without my guy
You went back to what you knew
So far removed from all that we went through
And I tread a troubled track
My odds are stacked
I'll go back to black

Literally, the perfect song for the darkness that comes before the light following a breakup. Ranks high on the emo scale. 

18. I'd Rather Go Blind by Beyonce

Something deep down in my soul said, "cry girl",
When I saw you and that girl, walking out.

Ooo I would rather, I would rather go blind boy,
Than to see you, walk away from me child, and all
Ooooo so you see, I love you so much
That I don't want to watch you leave me baby,
Most of all, I just don't, I just don't want to be free no

Ooo I was just, I was just, I was just sitting here thinking
Of your kiss and your warm embrace, yeah,
When the reflection in the glass that I held to my lips, now baby,
Revealed the tears that was on my face, yeah.

Originally sung by Etta James, Beyonce remade this depressingly sad song for the Cadillac Record movie.

19. Someone Like You by Adele

Old friend, why are you so shy?
Ain't like you to hold back or hide from the light.

I hate to turn up out of the blue uninvited
But I couldn't stay away, I couldn't fight it.
I had hoped you'd see my face and that you'd be reminded
That for me it isn't over.

Never mind, I'll find someone like you
I wish nothing but the best for you too
Don't forget me, I beg
I'll remember you said,
"Sometimes it lasts in love but sometimes it hurts instead,
Sometimes it lasts in love but sometimes it hurts instead"

Hats of to Adele for doing it yet again. This song rehashes the feelings of being unwanted and desperation for your love to be reciprocated...eventually. 

20. Every Little Bit by Alicia Keys
Every little hurt counts 
Every little hurt counts 
You say you're coming home 
Yet you'd never phone 
Leave me all alone 
My love is strong for you 
I'd do wrong for you
I can't take this loneliness you've given me 
I can't go on giving my life away 
Come back to me 
Darling you'll see 
I can give you all the things that you wanted before 
If you will stay with me
The first couple months after a breakup hit the hardest and sometimes, it feels like you're so alone despite having all the emotional support of your friends. Being alone doesn't have to be a lonely experience but it often feels that way — especially when you're coming out of a one-sided relationship. It's like the peak of loneliness.
21. Apologize by Timbaland & One Republic
You tell me that your sorry
Didn't think I'd turn around 
And say
That it's too late to apologize
It's too late
Said it's too late to apologize
It's too late
I take another chance, take a fall, take a shot from you
I need you like a heart needs a beat
It's not from you (Yeaaaa)
I loved you with a fire red and now it's turnin' blue
And to say
Sorry like the angel
Heaven let me think was you
Best tune for when you're no longer accepting the bullsh*t. Don't bother "apololying" to me — your number will be blocked.

22. Say Something I'm Giving Up On You by A Great Big World featuring Christina Aguilera

And I... am feeling so small
It was over my head
I know nothing at all
And I... will stumble and fall
I'm still learning to love
Just starting to crawl

Say something, I'm giving up on you
I'm sorry that I couldn't get to you
Anywhere I would've followed you
Say something, I'm giving up on you

This one perfectly depicts the moments where you know that if they were to say the right thing, right now the outcome would be so different — when you're trying to pull the words out of them but you know that there's only so much fighting you can do for the both of you.

23. I'm Goin' Down by Mary J. Blige

And the sound of the rain
Against my windowpane
Is slowly, is slowly drivin' me insane, boy

I'm goin' down
I'm goin' down
Cause you ain't around baby
My whole world's upside down

Sleep don't come easy
Boy please believe me
Since you been gone
Everything's goin' wrong
Why'd you have to say goodbye
Look what you've done to me
I can't stop these tears from fallin' from my eyes

Ooh baby

The song was first done by Rose Royce, but brought back to life in the '90s with Mary J's sultry voice and to this day, this song is the simplest yet most accurate description of being dumped.
24. Addicted by Simple Plan

Since the day I met you
And after all we've been through
I'm still a dick, I'm addicted to you
I think you know that it's true
I'd run a thousand miles to get you
Do you think I deserve this
I tried to make you happy
I did all that I could
Just to keep you
But you left anyway

I'm trying to forget that
I'm addicted to you
But I want it and I need it
I'm addicted to you
Now it's over, can't forget what you said
And I never, want to do this again
Heart breaker, heart breaker

My introduction to Simple Plan was "Addicted," and they changed the way I viewed music forever with this song. Anyhow, this song is about losing that high you get from being around someone you really loved and it puts our fiendish ways in perspective, for sure. 

25. On Bended Knee by Boys II Men 
Darlin' I can't explain, where did we lose our way
Girl, it's drivin' me insane and I know
I just need one more chance to prove my love to you
If you come back to me I guarantee that I'll never let you go.
can we go back to the days our love was strong.
Can you tell me how a perfect love goes wrong.
Can somebody tell me how you get things back the way it used to be
Oh God give me the reason, I'm down on bended knees
I'll never walk again until you come back to me I'm down on bended knees.
So much love, so much begging. Gotta love the 90s.
26. If I Ever Fall in Love Again by Shai

And if I ever (ever fall) in love again (again)
I will be sure that the lady is a friend
And if I ever (ever fall) in love so true (true)
I will be sure that the lady's just like you

Oh, yeah, the very next time she'll be my friend

This song sheds light on real love, as he discloses that he wants to find someone like his ex — a friend and a love — the next time we love. So often we forget to appreciate people after we part from them, but not these fellas. And, that's how you know it's real. 

27. She's Out of My Life by Michael Jackson
She's out of my life
She's out of my life
And I don't know whether to laugh or cry
I don't know whether to live or die
And it cuts like a knife
She's out of my life
It's out of my hands
It's out of my hands
To think for two years she was here
And I took her for granted I was so cavalier
Now the way that it stands
She's out of my hands
I've never even heard this song until now, but just look at the damn lyrics. How can that not break your heart, just listening? It melts my soul and was clearly the inspiration behind Bruno's suicidal hits. 
28. I Try by Macy Gray

I play it off, but I'm dreaming of you
And I'll keep my cool, but I'm fiendin'

I try to say goodbye and I choke
Try to walk away and I stumble
Though I try to hide it, it's clear
My world crumbles when you are not here
Goodbye and I choke
I try to walk away and I stumble
Though I try to hide it, it's clear
My world crumbles when you are not here

One of the more underrated songs and aspects of a falling relationship, Macy Gray gushed about the pain that comes with having to walk away from something you thought was promising. 
29. Hopeless by Farris Dionne

Hello mornin'
I sure missed you last night
Goodbye mornin'
You just won't do me right

But I've stayed just a little too long
Now it's time for me to move on

They say I'm hopeless
Penny with a hole in it
They say I'm no less
Than up to my head in it

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This song is laced with metaphors about moving on is all about the moment you decide that it's time to stop looking at the past and take a step forward to see what the future might.