The 40 Best Breakup Songs Of All Time

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

Charli Penn Jun, 23, 2011

1 of 40

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!

2 of 40

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!

3 of 40

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!

4 of 40

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!

5 of 40

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!

6 of 40

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

7 of 40

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!

8 of 40

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

9 of 40

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 of 40

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 of 40

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 of 40

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 of 40

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 of 40

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 of 40

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 of 40

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 of 40

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 of 40

“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 of 40

“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 of 40

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 of 40

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

22 of 40

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 of 40

“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 of 40

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 of 40

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 of 40

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

27 of 40

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 of 40

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

29 of 40

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 of 40

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 of 40

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 of 40

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 of 40

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 of 40

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 of 40

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 of 40

“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 of 40

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 of 40

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

39 of 40

Classic. Ladies. Breakup. Anthem!

40 of 40

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!