29 Sad Breakup Songs Guaranteed To Make You Ugly Cry

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sad woman
Heartbreak

Breakups are hard to get through, no matter the circumstances.

Music can almost always help you move past the pain, but sometimes, it's so deep and relatable that it can make you relive memories you hoped to blocked out. Even worse are the songs that put you in the artist's shoes without experiencing anything the lyrics talk about.

This tends to happen every time I listen to the Waiting to Exhale soundtrack — the words of those sad breakup songs force me to become a middle-age mother of two, whose husband left her after 13 years. And that's deeper than anything I could feel.

29 Best Sad Breakup Songs

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What do we know about that kind of heartache and strength? Well, we know the great mood-altering impact of music. And these songs are likely to reduce you to tears whenever you listen to them.

1. "Why Does It Hurt So Bad" by Whitney Houston

This Whitney song perfectly sums up the confusion that comes along with ending a relationship you knew was over from the very start. Yet after the breakup, you can't help but miss him. It's an inevitable emotion, but slightly more confusing in these instances.

"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"

2. "When I Was Your Man" by Bruno Mars

A song filled with regret and so much love — we only hope to find this kind of man someday — Mars learns from his past mistakes and wants only the best for you.

"​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"

3. "Rolling in the Deep" by Adele

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.

"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"

4. "Wrecking Ball" by Miley Cyrus

Written about the decay of a relationship, possibly her split with now ex-husband Liam Hemsworth, this song is proof that loving someone is risky business.

"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 wreck me

Yeah, you, you wreck me"

5. "End of the Road" by Boyz II Men

This song marked a period in time when love meant something, and even when people messed up they didn't have too much pride to beg you. Well, at least not the guys from Boyz II Men.

"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"

6. "Breakeven" by The Script

There's nothing more difficult than experiencing heartache while the other person goes on with life. "Breakeven" does a perfect job at conveying how it feels as you try not to watch them move on, while you struggle to break free of the pain.

"They say bad things happen for a reason

But no wise words gonna stop the bleeding

'Cause she's moved on while I'm still grieving

And when a heart breaks no it don't breakeven, even, no

And what am I going to do when the best part of me was always you? And

What am I supposed to say when I'm all choked up and you're OK?

I'm falling to pieces, yeah"

7. "What Hurts the Most" by Rascal Flatts

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

"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"

RELATED: How Guys Really Feel After A Breakup, According To Men

8. "Emotions" by Bee Gees

Ending a relationship is an emotional process. And in this Bee Gees classic, it's all about the emotional rollercoaster we've been on at one point or another.

"In the words of a broken heart

It's just emotion that's taken me over

Tied up in sorrow, lost in my soul

But if you don't come back

Come home to me, darling

You know that there'll be nobody left in this world to hold me tight

Nobody left in this world to kiss goodnight"

9. "What's Left of Me" by Nick Lachey

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.

"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"

10. "Everytime" by Britney Spears

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?

"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"

11. "It Will Rain" by Bruno Mars

Before Bruno Mars was cranking out disco hits, it was his relatable love ballads that won us over. Heartbreak leaves you feeling like you're near death, and this song still resonates to the core.

"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"

12. "Torn" by Natalie Imbruglia

The end of a relationship can lead to silence, where you remember everything you and your ex did together. But in the light of day, you can be reminded that a relationship built on "illusion" would never succeed.

"There's nothin' where he used to lie

The conversation has run dry

That's what's goin' on

Nothing's fine, I'm torn

I'm all out of faith

This is how I feel

I'm cold and I am shamed

Lying naked on the floor

Illusion never changed

Into something real

I'm wide awake and I can see

The perfect sky is torn

You're a little late

I'm already torn"

13. "Over My Head (Cable Car)" by The Fray

For anyone and everyone who refuses to let go without a fight, this song is for you. Hang in there.

"And suddenly I become a part of your past

I'm becoming the part that don't last

I'm losing you and it's 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 'til we torch it ourselves"

RELATED: The 5 Not-So-Pretty (But Totally Normal) Stages Of Breakup Grief

14. "Don't Speak" by No Doubt

Written after her devastating breakup with band mate Tony Kanal, Gwen Stefani eventually revealed, "It used to be more upbeat, more of a Seventies rock-type thing. [When] Tony and I broke up... it turned into a sad song."

"Our memories, well, they can be inviting

But some are altogether mighty frightening

As we die, both you and I

With my head in my hands, I sit and cry

Don't speak, I know just what you're sayin'

So please stop explainin'

Don't tell me 'cause it hurts, no, no, no

Don't speak, I know what you're thinkin'

And I don't need your reasons

Don't tell me 'cause it hurts"

15. "Somebody That I Used I Know" by Gotye ft. Kimbra

When the person you thought you knew best becomes a complete stranger, you find a way to be relieved despite your obvious state of love sickness. Weird how that works, huh?

"But you didn't have to cut me off

Make out like it never happened and that we were nothing

And I don't even need your love

But you treat me like a stranger and that feels so rough

No, you didn't have to stoop so low

Have your friends collect your records and then change your number

I guess that I don't need that though

Now you're just somebody that I used to know"

16. "Let It Flow" by Toni Braxton

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

"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"

17. "Back to Black" by Amy Winehouse

Literally the perfect song for the darkness that comes before the light following a breakup!

"We only said goodbye with words

I died a hundred times

You go back to her

And I go back to

We only said goodbye with words

I died a hundred times

You go back to her

And I go back to black"

18. "I'd Rather Go Blind" by Beyoncé

Originally sung by Etta James, Beyoncé's did a cover of this depressingly sad song Cadillac Records.

"Ooo I would rather, I would rather go blind boy

Than to see you, walk away from me child, and all

Ooo 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"

19. "Someone Like You" by Adele

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

"I hate to turn up out of the blue uninvited

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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"

20. "Every Little Bit" by Alicia Keys

The first few months after a breakup hit the hardest, and sometimes it feels lonely despite having all the emotional support of 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.

"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"

21. "Apologize" by Timbaland ft. One Republic

This is the best tune for when you're no longer accepting the fake apologies. Don't bother — your number will be blocked.

"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

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"

RELATED: 100 Breakup Quotes For Him To See Just How Much You Miss Being Together

22. "Say Something (I'm Giving Up On You)" by A Great Big World ft. Christina Aguilera

This sad song perfectly depicts the moments where you know that if they were to say the right thing, the outcome would be different. But there is only so much fighting you can do.

"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"

23. "I'm Goin' Down" by Mary J. Blige

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

"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, I'm goin' down"

24. "Foolish Games" by Jewel

Originally written as a poem about a boy Jewel fell in love with when she was a teenager, her words were turned into lyrics, showing us what deep, deep heartbreak sounds like.

"Well in case you failed to notice

In case you failed to see

This is my heart bleeding before you

This is me down on my knees, and

These foolish games are tearing me apart

And your thoughtless words are breaking my heart

You're breaking my heart"

 

25. "On Bended Knee" by Boyz II Men

So much love, so much begging, again from these gentlemen. You've just got to love the 90s.

"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"

26. "If I Ever Fall In Love" by Shai

This song sheds light on real love, and the yearning to find someone like your ex the next time you fall in love. We forget to appreciate people after we part from them, but that is how you know it's real.

"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"

27. "She's Out of My Life" by Michael Jackson

Just listen to those lyrics! How can that not break your heart? It melts your soul to the core.

"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"

28. "I Try" by Macy Gray

One of the more underrated songs about a failing relationship, Macy Gray gushes about the pain that comes with having to walk away from something you thought was promising.

"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"

29. "Hopeless" by Farris Dionne

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

"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"

RELATED: 5 Crucial Things To Remember When Getting Over A Breakup Feels Impossible

Kiarra Sylvester is a freelance writer and contributor to YourTango, HuffPost, CafeMom, xoNecole.com, and more.