For every song that captures the ebullience of love, like “Glad All Over” by the Dave Clark Five, there is a tune that taps into the melancholia of breaking up, such as “Try Sleeping With a Broken Heart” by Alicia Keys. Breakup songs are among the most popular and beloved because the lyrics are heartfelt — and because we’ve all been there.
Songs about breaking up cut across generations and genres, and that is reflected in the 24/7 Wall St. list of the best breakup songs. Many of the songs were released in the 1960s, including such torch-song classics as Patsy Cline’s “Crazy” and “You’ve Lost That Lovin’ Feeling” by the Righteous Brothers. More recently, artists such as Adele (“Rolling in the Deep”) and Bruno Mars (“When I Was Your Man”) have plumbed the depths of painful breakups.
Some breakup songs are defiant, like Cee Lo Green’s “F**k You! (Forget You),” or fierce, such as Lily Allen’s “Smile.” Others are agonizing, such as Bill Withers’ “Ain’t No Sunshine.” Other songs pine for reuniting, like Mariah Carey’s “We Belong Together.”
Even though these artists are singing about heartbreak, some of these songs, like Gloria Gaynor’s “I Will Survive,” Kelly Clarkson’s “Stronger (What Doesn’t Kill You),” and Fergie’s “Big Girls Don’t Cry,” express the belief that there is life to be lived after the end of a relationship.
Click here to see the best breakup songs.
Click here to see our methodology.
50. “Big Girls Don’t Cry” by The Four Seasons
> Billboard debut: October 20, 1962
> Weeks on Billboard Hot 100: 16
> Peak position: 1
> Est. cover versions: 17
“Shame on you your mama said / Shame on your, you cried in bed / Shame on you, you told a lie / Big girls do cry.”
[in-text-ad]
49. “Here Without You” by 3 Doors Down
> Billboard debut: August 30, 2003
> Weeks on Billboard Hot 100: 51
> Peak position: 5
> Est. cover versions: 12
“A hundred days have made me older / Since the last time that I saw your pretty face. / A thousand lies have made me colder / And I don’t think I can look at this the same.”
48. “Sorry Seems To Be The Hardest Word” by Elton John
> Billboard debut: November 13, 1976
> Weeks on Billboard Hot 100: 14
> Peak position: 6
> Est. cover versions: 99
“What have I got to do to make you love me? / What have I got to do to make you care?”
47. “What Becomes Of The Brokenhearted” by Jimmy Ruffin
> Billboard debut: August 20, 1966
> Weeks on Billboard Hot 100: 17
> Peak position: 7
> Est. cover versions: 63
“The roots of love grow all around / But for me they come a tumblin’ down. / Every day heartaches grow a little stronger / I can’t stand this pain much longer.”
[in-text-ad-2]
46. “Believe” by Cher
> Billboard debut: December 19, 1998
> Weeks on Billboard Hot 100: 31
> Peak position: 1
> Est. cover versions: 29
“I can feel something inside me say / I really don’t think you’re strong enough, no / Do you believe in life after love?”
45. “You’re So Vain” by Carly Simon
> Billboard debut: December 02, 1972
> Weeks on Billboard Hot 100: 17
> Peak position: 1
> Est. cover versions: 44
“You’re so vain / You probably think this song is about you. / Don’t you? / Don’t you?”
[in-text-ad]
44. “Angie” by The Rolling Stones
> Billboard debut: September 08, 1973
> Weeks on Billboard Hot 100: 16
> Peak position: 1
> Est. cover versions: 64
“With no loving in our souls / And no money in our coats / You can’t say we’re satisfied.”
43. “The Sign” by Ace Of Base
> Billboard debut: January 01, 1994
> Weeks on Billboard Hot 100: 41
> Peak position: 1
> Est. cover versions: 9
“Under the pale moon / For so many years I’ve wondered who you are. / How could a person like you bring me joy?”
42. “We Belong Together” by Mariah Carey
> Billboard debut: April 16, 2005
> Weeks on Billboard Hot 100: 43
> Peak position: 1
> Est. cover versions: 5
“When you left, I lost a part of me / It’s still so hard to believe.”
[in-text-ad-2]
41. “Since U Been Gone” by Kelly Clarkson
> Billboard debut: December 18, 2004
> Weeks on Billboard Hot 100: 46
> Peak position: 2
> Est. cover versions: 14
“How come I’d never hear you say / I just wanna be with you? / I guess you never felt that way.”
40. “Love The Way You Lie” by Eminem feat. Rihanna
> Billboard debut: July 10, 2010
> Weeks on Billboard Hot 100: 29
> Peak position: 1
> Est. cover versions: 11
“Just gonna stand there and watch me burn? / Well, that’s alright because I like the way it hurts.”
[in-text-ad]
39. “Nobody Knows” by The Tony Rich Project
> Billboard debut: December 16, 1995
> Weeks on Billboard Hot 100: 47
> Peak position: 2
> Est. cover versions: 6
“Why didn’t I say / The things I needed to say / How could I let my angel get away?”
38. “The Winner Takes It All” by ABBA
> Billboard debut: November 22, 1980
> Weeks on Billboard Hot 100: 26
> Peak position: 8
> Est. cover versions: 105
“But tell me, does she kiss / Like I used to kiss you? / Does it feel the same / When she calls your name?”
37. “Apologize” by Timbaland feat. OneRepublic
> Billboard debut: April 21, 2007
> Weeks on Billboard Hot 100: 47
> Peak position: 2
> Est. cover versions: 37
“You tell me that you’re sorry, didn’t think I’d turn around / And say / It’s too late to apologize.”
[in-text-ad-2]
36. “Don’t You Want Me” by The Human League
> Billboard debut: March 06, 1982
> Weeks on Billboard Hot 100: 28
> Peak position: 1
> Est. cover versions: 51
“I was working as a waitress in a cocktail bar / That much is true. / But even then I knew I’d find a much better place / Either with or without you.”
35. “Total Eclipse Of The Heart” by Bonnie Tyler
> Billboard debut: July 16, 1983
> Weeks on Billboard Hot 100: 29
> Peak position: 1
> Est. cover versions: 49
“Once upon a time I was falling in love / Now I’m only falling apart.”
[in-text-ad]
34. “Let Her Go” by Passenger
> Billboard debut: August 17, 2013
> Weeks on Billboard Hot 100: 43
> Peak position: 5
> Est. cover versions: 34
“You see her when you close your eyes / Maybe one day you’ll understand why / Everything you touch surely dies.”
33. “50 Ways To Leave Your Lover” by Paul Simon
> Billboard debut: December 20, 1975
> Weeks on Billboard Hot 100: 17
> Peak position: 1
> Est. cover versions: 77
“She said it grieves me so / To see you in such pain / I wish there was something I could do / To make you smile again. / I said I appreciate that / And would you please explain / About the fifty ways.”
32. “Attention” by Charlie Puth
> Billboard debut: May 13, 2017
> Weeks on Billboard Hot 100: 40
> Peak position: 5
> Est. cover versions: 29
“You just want attention, you don’t want my heart. / Maybe you just hate the thought of me with someone new.”
[in-text-ad-2]
31. “When I Was Your Man” by Bruno Mars
> Billboard debut: December 22, 2012
> Weeks on Billboard Hot 100: 35
> Peak position: 1
> Est. cover versions: 44
“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.”
30. “How Can You Mend A Broken Heart” by Bee Gees
> Billboard debut: June 26, 1971
> Weeks on Billboard Hot 100: 15
> Peak position: 1
> Est. cover versions: 69
“How can you mend this broken man? / How can a loser ever win? / Please help me mend my broken heart and let me live again.”
[in-text-ad]
29. “Stronger (What Doesn’t Kill You)” by Kelly Clarkson
> Billboard debut: November 12, 2011
> Weeks on Billboard Hot 100: 37
> Peak position: 1
> Est. cover versions: 16
“You heard that I was starting over with someone new / They told you I was moving on and over you.”
28. “I’m Sorry” by Brenda Lee
> Billboard debut: May 30, 1960
> Weeks on Billboard Hot 100: 33
> Peak position: 1
> Est. cover versions: 38
“You tell me mistakes / Are part of being young / But that don’t right / The wrong that’s been done.”
27. “Before He Cheats” by Carrie Underwood
> Billboard debut: September 16, 2006
> Weeks on Billboard Hot 100: 64
> Peak position: 8
> Est. cover versions: 11
“I dug my key into the side / Of his pretty little souped up four-wheel drive / Carved my name into his leather seats. / I took a Louisville slugger to both headlights / Slashed a hole in all four tires / Maybe next time, he’ll think before he cheats.”
[in-text-ad-2]
26. “Big Girls Don’t Cry” by Fergie
> Billboard debut: May 05, 2007
> Weeks on Billboard Hot 100: 48
> Peak position: 1
> Est. cover versions: 5
“And I’m gonna miss you like a child misses their blanket / But I’ve got to get a move on with my life. / It’s time to be a big girl now / And big girls don’t cry.”
25. “Un-Break My Heart” by Toni Braxton
> Billboard debut: October 26, 1996
> Weeks on Billboard Hot 100: 42
> Peak position: 1
> Est. cover versions: 34
“I can’t forget the day you left. / Time is so unkind / And life is so cruel without you here beside me.”
[in-text-ad]
24. “Against All Odds (Take A Look At Me Now)” by Phil Collins
> Billboard debut: February 25, 1984
> Weeks on Billboard Hot 100: 24
> Peak position: 1
> Est. cover versions: 86
“I wish I could just make you turn around / Turn around and see me cry. / There’s so much I need to say to you / So many reasons why / You’re the only one who really knew me at all.”
23. “If You Leave Me Now” by Chicago
> Billboard debut: August 14, 1976
> Weeks on Billboard Hot 100: 21
> Peak position: 1
> Est. cover versions: 87
“Oooooh no, baby, please don’t go.”
22. “New Rules” by Dua Lipa
> Billboard debut: August 19, 2017
> Weeks on Billboard Hot 100: 53
> Peak position: 6
> Est. cover versions: 20
“I keep pushin’ forwards, but he keeps pullin’ me backwards / Now I’m standin’ back from it, I finally see the pattern.”
[in-text-ad-2]
21. “Wrecking Ball” by Miley Cyrus
> Billboard debut: September 07, 2013
> Weeks on Billboard Hot 100: 32
> Peak position: 1
> Est. cover versions: 61
“Don’t you ever say I just walked away / I will always want you.”
20. “Grenade” by Bruno Mars
> Billboard debut: October 16, 2010
> Weeks on Billboard Hot 100: 36
> Peak position: 1
> Est. cover versions: 31
“Yes, I would die for ya, baby / But you won’t do the same.”
[in-text-ad]
19. “I Will Survive” by Gloria Gaynor
> Billboard debut: December 16, 1978
> Weeks on Billboard Hot 100: 27
> Peak position: 1
> Est. cover versions: 99
“Weren’t you the one who tried to hurt me with goodbye? / Did you think I’d crumble? Did you think I’d lay down and die? / Oh no, not I, I will survive.”
18. “You Were Meant For Me” by Jewel
> Billboard debut: November 30, 1996
> Weeks on Billboard Hot 100: 65
> Peak position: 2
> Est. cover versions: 7
“Put on my coat in the pouring rain / I saw a movie and it just wasn’t the same. / ‘Cause it was happy or I was sad / And it made me miss you oh so bad ’cause / Dreams last for so long / Even after you’re gone.”
17. “Stitches” by Shawn Mendes
> Billboard debut: June 13, 2015
> Weeks on Billboard Hot 100: 52
> Peak position: 4
> Est. cover versions: 33
“And now that I’m without your kisses / I’ll be needing stitches.”
[in-text-ad-2]
16. “Somebody That I Used To Know” by Gotye feat. Kimbra
> Billboard debut: January 21, 2012
> Weeks on Billboard Hot 100: 59
> Peak position: 1
> Est. cover versions: 49
“But you didn’t have to cut me off / Make out like it never happened and that we nothing. / And I don’t even need your love / But you treat me like a stranger and that feels so rough.”
15. “F**k You! (Forget You)” by CeeLo Green
> Billboard debut: September 11, 2010
> Weeks on Billboard Hot 100: 48
> Peak position: 2
> Est. cover versions: 27
“And though there’s pain in my chest / I still wish you the best / With a f**k you.”
[in-text-ad]
14. “Alone Again (Naturally)” by Gilbert O’Sullivan
> Billboard debut: June 17, 1972
> Weeks on Billboard Hot 100: 18
> Peak position: 1
> Est. cover versions: 125
“Leaving me to doubt / All about God and His mercy / For if He really does exist / Why did He desert me?”
13. “Love Yourself” by Justin Bieber
> Billboard debut: December 05, 2015
> Weeks on Billboard Hot 100: 41
> Peak position: 1
> Est. cover versions: 58
“My mama don’t like you and she likes everyone / And I never like to admit that I was wrong / And I’ve been so caught up in my job, didn’t see what’s going on / And now I know, I’m better sleeping on my own.”
12. “Crazy” by Patsy Cline
> Billboard debut: October 23, 1961
> Weeks on Billboard Hot 100: 11
> Peak position: 9
> Est. cover versions: 231
“I’m crazy for trying, and crazy for crying / And I’m crazy for loving you.”
[in-text-ad-2]
11. “Someone Like You” by Adele
> Billboard debut: March 12, 2011
> Weeks on Billboard Hot 100: 39
> Peak position: 1
> Est. cover versions: 62
“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.”
10. “Walk On By” by Dionne Warwick
> Billboard debut: April 25, 1964
> Weeks on Billboard Hot 100: 13
> Peak position: 6
> Est. cover versions: 188
“Foolish pride, that’s all that I have left / So let me hide / The tears and the sadness you gave me / When you said goodbye.”
[in-text-ad]
9. “How Do I Live” by LeAnn Rimes
> Billboard debut: June 21, 1997
> Weeks on Billboard Hot 100: 69
> Peak position: 2
> Est. cover versions: 34
“How do I live without you? I want to know / How do I breathe without you if you ever go?”
8. “Every Breath You Take” by The Police
> Billboard debut: June 04, 1983
> Weeks on Billboard Hot 100: 22
> Peak position: 1
> Est. cover versions: 157
“Since you’ve gone, I’ve been lost without a trace. / I dream at night I can only see your face / I look around but it’s you I can’t replace / I feel so cold and I long for your embrace.”
7. “Need You Now” by Lady Antebellum
> Billboard debut: August 29, 2009
> Weeks on Billboard Hot 100: 60
> Peak position: 2
> Est. cover versions: 29
“It’s a quarter after one, I’m all alone and I need you now. / Said I wouldn’t call, but I lost all control and I need you now.”
[in-text-ad-2]
6. “Breaking Up Is Hard To Do” by Neil Sedaka
> Billboard debut: June 30, 1962
> Weeks on Billboard Hot 100: 28
> Peak position: 1
> Est. cover versions: 86
“I beg of you, don’t say goodbye. / Can’t we give our love just one more try? / Come on baby, let’s start anew. / ‘Cause breaking up is hard to do.”
5. “These Boots Are Made For Walkin'” by Nancy Sinatra
> Billboard debut: January 22, 1966
> Weeks on Billboard Hot 100: 14
> Peak position: 1
> Est. cover versions: 165
“You keep playing where you shouldn’t be playing / And you keep thinking that you’ll never get burnt / Well, I’ve just found me a brand new box of matches / And he knows you ain’t had time to learn.”
[in-text-ad]
4. “You’ve Lost That Lovin’ Feelin'” by The Righteous Brothers
> Billboard debut: December 12, 1964
> Weeks on Billboard Hot 100: 16
> Peak position: 1
> Est. cover versions: 190
“You’re trying hard not to show it / But baby, baby I know it. / You’ve lost that lovin’ feeling.”
3. “Ain’t No Sunshine” by Bill Withers
> Billboard debut: July 17, 1971
> Weeks on Billboard Hot 100: 16
> Peak position: 3
> Est. cover versions: 231
“Ain’t no sunshine when she’s gone / And she’s always gone too long anytime she goes away.”
2. “Rolling In The Deep” by Adele
> Billboard debut: December 25, 2010
> Weeks on Billboard Hot 100: 65
> Peak position: 1
> Est. cover versions: 84
“The scars of your love / They leave me breathless. / I can’t help feeling / We could have had it all.”
[in-text-ad-2]
1. “Yesterday” by The Beatles
> Billboard debut: September 25, 1965
> Weeks on Billboard Hot 100: 11
> Peak position: 1
> Est. cover versions: 665
“Why she had to go? / I don’t know, she wouldn’t say. / I said something wrong. / Now I long for yesterday.”
Methodology
To determine the best breakup songs, 24/7 Wall St. created an index of approximately 450 heartbreak-related songs based on Billboard Hot 100 performance and the number of times the song has been covered. The peak position a song reached on the Billboard Hot 100 was given full weight in the index. The number of weeks a song was on the Billboard Hot 100 and at what position, adjusted for average chart turnover at the time of the song’s release, was given half weight in the index. The estimated number of times a song has been covered, based on data from SecondHandSongs, was given full weight in the index. Only songs that were included on other “best breakup song” lists from various media sources were considered.
Get Ready To Retire (Sponsored)
Start by taking a quick retirement quiz from SmartAsset that will match you with up to 3 financial advisors that serve your area and beyond in 5 minutes, or less.
Each advisor has been vetted by SmartAsset and is held to a fiduciary standard to act in your best interests.
Here’s how it works:
1. Answer SmartAsset advisor match quiz
2. Review your pre-screened matches at your leisure. Check out the advisors’ profiles.
3. Speak with advisors at no cost to you. Have an introductory call on the phone or introduction in person and choose whom to work with in the future
Get started right here.
Thank you for reading! Have some feedback for us?
Contact the 24/7 Wall St. editorial team.