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Home · Love & Sex

The 40 Best Breakup Songs Of All Time

Having a rough breakup? One of these hits will get you through it.

By Charli Penn · June 23, 2011October 28, 2020
01
“Where Do Broken Hearts Go” by Whitney Houston

There is still no answer to the famous question Whitney Houston posed over 20 years ago, but it hasn’t made us love this classic any less. Listen here!

02
“Ex-Factor’ by Lauryn Hill

Lauryn really outdid herself on this one. We might have all been “miseducated” on love back then, but Ms. Hill sure set us straight. Listen here!

03
“Unbreak My Heart”

Toni sang this song so well it made women all over the world line up for a cure. Sadly, there is no cure for a broken heart, but this song is definitely the next best thing. Listen here!

04
“Again” by Janet Jackson

On this track Ms. Jackson vows to never fall in love again with a man she clearly still loved. Sound complicated, right? As many of u know, love’s like that sometimes. Listen here!

05
“Used to Love Me” by Faith Evans

This one goes out to all the ladies who remember the way he used to love them, and seriously wish they could forget. Listen here!

06
“Emotional Rollercoaster” by Vivian Green

Loves ups and downs were perfectly put to music on this contagious ballad and all women sang along. Listen here!

07
“Fallin” by Alicia Keys

When else have bad feelings ever sounded so good? Not only was Alicia singing right from our souls with this one, but she also delivered the lyrics with resounding strength and sass. We’re not always sure who to love, but we are sure about loving this song. Listen here!

08
“Irreplaceable” by Beyonce

This instant classic from Queen Bey had women worldwide sending brothers headed “to the left to the left.” Listen here!

09
“Caught Out There” by Kelis

This bold single came out of nowhere and stole our hearts. Kelis made it okay to hate him, at least for a little while, and easy to love her. Listen here!

10
“I’m Goin’ Down” by Mary J. Blige

When he turns your world upside down and “sleep don’t come easy” you can always count on a Mary record to be there. Listen here!

11
“We Can’t Be Friends” by Deborah Cox and R.L.

Sung in perfect harmony, Deborah and R.L. remind us of how much it hurts to know things will never be the same. Lyrics We Love: “Don’t get too close to me and expect me to behave. I might just steal a kiss if you come near my face”. Listen here!

12
“Burn” by Usher

A smooth-talking Usher preached of letting go on this instant hit breakup ballad.  Lyrics We Love: “I do but you don’t think it’s best we go our separate ways. Tell me why I should stay in this relationship when I’m hurting baby. I ain’t happy baby.” Listen here!

13
“Cross My Mind’ by Jill Scott

The ultimate ode to reminiscing about love long gone. Jill kept it more than real on this ballad, closing the song with the classic and unforgettable line: “But the reality of it is, you were never good for me and I was never good for you.
I just remember what we used to do….” Listen here!

14
“Another Again” by John Legend

The perfect ode to going back to the guy you know you shouldn’t be with in the first place. Lyrics we love: “Oh we did it again. Knowing we should quit it, but we simply won’t admit it again. Oh it feels good, it’s so good, but I won’t do it again. It’s so dramatic again. After we go at it, we get mad then we go at it again. Oh I love it, then I hate it.” Listen here!

15
“Tyrone” by Erykah Badu

When Erykah sat on the live stage and performed this song it became an instant and iconic hit. The phrase “I think you better call Tyrone” took on new meaning for all of us. Listen here!

16
“Bust Your Windows” by Jazmine Sullivan

For the times you’re so hurt you don’t want to be the better person. Lyrics We Love: “I must admit it helped a little bit, to think of how you’d feel when you saw it. I didn’t know that I had that much strength. But I’m glad you see what happens when…You see you cant just play with people’s feelings. Tell them you love them but don’t mean it. You probably say that it was juvenile, but I think that I deserve to smile” Listen here!

17
“Not Gon Cry” by Mary J. Blige

This song alone dried up tears around the world. It was the beginning of a new era of breakup music where women didn’t get mad, they got even. Listen here!

18
Emotional by “Carl Thomas”

“What is a man to do when he just can’t take no more?” Apparently write one of the most moving love songs ever! We’re still thanking Carl for this one. Listen here!

19
“The One I Gave My Heart To” by Aaliyah

“How could the one I gave my heart to break my heart so bad”? Who hasn’t asked themselves this question at least once before? If you’ve got the answer, be sure to let us know. Listen here!

20
“(My Lovin’) Never Gonna Get It” by En Vogue

A song for the times he had “so many chances to make change, but the only thing he changed was love to hate”. If he promised you the moon and stars and didn’t deliver ladies, this one’s for you. Listen here!

21
“Officially Missin You” by Tamia

It’s official, we miss this song! It was so honest, so raw, and so sweet all at the same time. Listen here!

22
“One Last Cry” by Brian McKnight

In the 90s, when Brian McKnight begged us for ‘one last cry’ we almost gave it to him. Call it a forgiveness anthem or healing 101, this record schooled us on the language of goodbyes. Listen here!

23
“All Cried Out” by Allure

“You were the one who left me neglected. Apology not accepted.” it’s wisdom like that that reminds us that lyrical genius Jill Scoot helped pen this hit. We don’t remember what happened to Allure, but we haven’t forgotten this song. Listen here!

24
“How Can You Mend A Broken Heart” by Al Green

Sometimes nothing can make the pain stop and songs like this remind you that you’re not the only one feeling like hope is gone. Lyrics We Love: How can you stop the sun from shining? What makes the world go round?
How can you mend this broken man? How can a loser ever win?” Listen here!

25
“Misty Blue” by Dorothy Moore

For the times when the pain just won’t go away.
Lyrics We Love:
“Oh, it’s been such a long, long time,
Looks like I get you off my mind,
Oh, but I can’t,
Just the thought of you,
Turns my whole world,
A misty blue.”

26
“Brokenhearted” by Brandy

Brandy’s teenage ode to recovering from heartache helped many young women also get past their pasts.

27
“Sleeping In My Bed” by Dru Hill

Sometimes love isn’t faithful or true. Lucky for us, we have songs like this one that say everything we feel so we don’t have to. Lyrics We Love: “I come home early expecting your warm embrace, but something is wrong ‘cuz its written all over your face. It hurt so bad when I walked through the door, but ’cha know one damn thing, baby I ain’t coming back no more.” Preach Sisqo!

28
“Anytime” by Brian McKnight

We could listen to this bittersweet tale of love gone wrong “anytime”.

29
“Deuces” by Chris Brown

Whether you’re a fan of the artist or not, there’s no denying this song is one of the best sassy send offs of all time. Deuces!

30
“Ephiphany” by Christte Michelle

This track has inspired many a girl-power moment for women so over their man’s B.S.

Lyrics We Love:
“I think I’m just about over being your girlfriend…I’m leaving, yeah!”

31
“After The Love Has Gone” by Earth, Wind and Fire

There isn’t a soul in the room who doesn’t want to raise a hand in the air and sing along to this one as Earth, Wind, and Fire take us to church. “Somethin’ happened along the way. What used to be happy was sad”….preach!

32
“Aint No Sunshine” by “Bill Withers”

The words to this song are some of the best known breakup lyrics of all time. Do you know anyone who doesn’t know the words? Right, we don’t either.

33
“I Wish I Wasn’t’ by Heather Headley

If we didn’t love them, the couldn’t hurt us, Ms. Headley so wisely points out. The most memorable line on this track? “I wish I could go back to the day before we met.” Ouch!

34
“I Never Loved A Man” by Aretha Franklin

This song’s for all the times your friends tried to tell you the guy you’re dating is just no good. But you didn’t listen because you loved him so. Aretha, we’ve all been there.

35
“Breakup to Makeup” by The Stylisitics

Sometimes love is all about just taking the long way right back home. This one goes out to anyone who’s ever loved someone one day and hated them the next.

36
“Free Yourself” by Fantasia

“If you don’t want me then don’t talk to me,” a soulful Fantasia belted out as she made this track one a broken heart will not soon forget.

37
“Keep On Walking” by CeCe Peniston

Before Bey was sending men off “to the left, to the left”, Ms. Peniston told them to “keep on walking” right on past her door.

38
“Where I Wanna Be” by Donell Jones

As Donell puts it best: “When you love someone you just don’t treat them bad.” Enough said.

39
“I Will Survive” by Diana Ross

Classic. Ladies. Breakup. Anthem!

40
“Infinity” by Mariah Carey

The newest ode to being totally over a love you thought would last forever comes from Mariah Carey. (Note: Carey claims this song has nothing to do with her recent divorce from ex-husband Nick Cannon.) Listen here!

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