The 50 Greatest Breakup Songs

Every breakup is like a snowflake; each one is different. Whether you’re left feeling sad, relieved, elated, or spiteful, there’s quite a spectrum of possible emotions to feel regardless if you’re the dumper or the dumpee. For generations, artists have channeled their own feelings surrounding the inevitable end to their relationships, and each perspective is unique. Here are the 50 Best Songs that deal with breakups from any and every angle… the good, the bad, and the insane.

50. Solange “Losing You”

Breakup Perspective: So…can we just admit that we’re done here?

Best Breakup Line: “I’m not the one that you should be making your enemy.”

49. Boyz II Men “End Of The Road”

Breakup Perspective: I know we’re done, but I can’t let go.

Best Breakup Line: “Pain in my head, oh I’d rather be dead. Spinning around and around.”

48. Carly Simon “You’re So Vain”

Breakup Perspective: There is no room for vanity in this relationship, ass.

Best Breakup Line: “You had me several years ago when I was still quite naive. Well you said we made such a pretty pair, and that you would never leave.”

47. Soft Cell “Tainted Love”

Breakup Perspective: Tryna get the hell outta dodge.

Best Breakup Line: “I love you though you hurt me so, now I’m gonna pack my things and go.”

46. Bee Gees “How Can You Mend A Broken Heart?”

Breakup Perspective: My heart is broken and I’m sad.

Best Breakup Line: “Please help me mend my broken heart, and let me live again.”

45. Taylor Swift “We Are Never Ever Getting Back Together”

Breakup Perspective: The title pretty much says it all.

Best Breakup Line: “Ooh we called it off again last night, but ooh, this time I’m telling you, I’m telling you we are never ever ever getting back together.”

44. Human League “Don’t You Want Me?”

Breakup Perspective: I’ve got all the power over you/You’ve got no power over me/We’re both nuts.

Best Breakup Line: “You know I don’t believe you when you say that you don’t need me.”

43. Paul Simon “50 Ways To Leave Your Lover”

Breakup Perspective: Textbook.

Best Breakup Line: “I’d like to help you in your struggle to be free. There must be fifty ways to leave your lover.”

42. Nancy Sinatra “These Boots Are Made For Walkin'”

Breakup Perspective: Oh you want to cheat on me? Let me tell you what’s going to happen.

Best Breakup Line: “You keep playin’ where you shouldn’t be playin’, and you keep thinkin’ that you’ll never get burnt. Ha! I just found me a brand new box of matches, yeah, and what he knows, you ain’t had time to learn.”

41. The Rolling Stones “Angie”

Breakup Perspective: Angie, you’re on swell lady, but this just isn’t going to work out.

Best Breakup Line: “With no loving in our souls and no money in our coats, you can’t say we’re satisfied.”

40. Otis Redding “Pain In My Heart”

Breakup Perspective: Ouch.

Best Breakup Line: “Pain in my heart just won’t let me sleep. Where can my baby be, Lord where can she be?”

39. R.E.M. “The One I Love”

Breakup Perspective: Well who am I going to use now?

Best Breakup Line: “A simple prop to occupy my time. This one goes out to the one I love.”

38. Michael Jackson “She’s Out Of My Life”

Breakup Perspective: For some reason, I didn’t learn my lesson with the “I Want You Back” girl…

Best Breakup Line: “So I’ve learned that love’s not possession, and I’ve learned that love won’t wait. Now I’ve learned that love needs expression, but I’ve learned too late.”

37. Blondie “Heart Of Glass”

Breakup Perspective: Stop using me, you’re breaking my heart.

Best Breakup Line: “Seemed like the real thing, but only to find much of mistrust, love’s gone behind.”

36. The Police “Can’t Stand Losing You”

Breakup Perspective: Woe is me… How can I live without you?

Best Breakup Line: “But you’ll be sorry when I’m dead, and all this guilt will be on your head.”

35. The Smiths “I Know It’s Over”

Breakup Perspective: This isn’t just any breakup… this is a melancholy Morrissey break up.

Best Breakup Line: “I know it’s over, and it never really began, but in my heart it was so real.”

34. Connie Francis “Lipstick On Your Collar”

Breakup Perspective: Busted.

Best Breakup Line: “Bet your bottom dollar you and I are through, cause lipstick on your collar told a tale on you.”

33. ABBA “The Winner Takes It All”

Breakup Perspective: You walked out of this with everything, and I’ve got nothing. Womp womp.

Best Breakup Line: “I was in your arms, thinking I belonged there. I figured it made sense, building me a fence. Building me a home.”

32. The Temptations “Ain’t Too Proud To Beg”

Breakup Perspective: I’ve got no shame! Please don’t leave me! (Please please please please please please…)

Best Breakup Line: “If I have to beg and plead for your sympathy, I don’t mind cause you mean that much to me.”

31. Bon Iver “Skinny Love”

Breakup Perspective: My brain…my heart… What…?

Best Breakup Line: “And I told you to be patient, and I told you to be fine, and I told you be balanced, and I told you to be kind.”

30. Blur “No Distance Left To Run”

Breakup Perspective: I’m exhausted. I need to move on with my life.

Best Breakup Line: “I won’t kill myself trying to stay in your life. I’ve got no distance left to run.”

29. Amy Winehouse “Back To Black”

Breakup Perspective: I’m still completely hung up on you, and you just went ahead and banged another chick. Cool.

Best Breakup Line: “And I tread a troubled track. My odds are stacked. I go back to black.”

28. Roy Orbison “Crying”

Breakup Perspective: Simply, I still love you.

Best Breakup Line: “I love you even more than I did before, but darling what can I do, for you don’t love me and I’ll always be crying over you.”

27. Gotye featuring Kimbra “Somebody That I Used To Know”

Breakup Perspective: Look, I’m good, but did you really have to cut me out of your life?

Best Breakup Line: “Well you said that we would still be friends, but I’ll admit that I was glad it was over.”

26. The Cure “Pictures Of You”

Breakup Perspective: All I’ve got left are my memories.

Best Breakup Line: “If only I’d thought of the right words, I wouldn’t be breaking apart all my picture of you.”

25. Bonnie Raitt “I Can’t Make You Love Me”

Breakup Perspective: I just have to accept the fact that you don’t love me.

Best Breakup Line: “You can’t make your heart feel something it won’t.”

24. Elvis Costello & The Attractions “I Want You”

Breakup Perspective: “Heartbroken” doesn’t even begin to cover it.

Best Breakup Line: “I want you so it scares me to death, and I can’t say anymore than I love you.”

23. Joni Mitchell “A Case Of You”

Breakup Perspective: I’m really just a mess without you.

Best Breakup Line: “Go to him, stay with him if you can, but be prepared to bleed.”

22. Willie Nelson “Always On My Mind”

Breakup Perspective: I know I was a jerk, but can we give it another go?

Best Breakup Line: “Little things I should have said and done, I just never took the time.”

21. Marvin Gaye “I Heard It Through The Grapevine”

Breakup Perspective: Man, news travels fast when you’re a liar and a cheat.

Best Breakup Line: “I know a man ain’t supposed to cry, but these tears I can’t hold inside.”

20. Bob Dylan “Don’t Think Twice, It’s Alright”

Breakup Perspective: Don’t worry about it, we’re cool (…bitch.)

Best Breakup Line: “You just kinda wasted my precious time, but don’t think twice, it’s alright.”

19. The Clash “Train In Vain”

Breakup Perspective: I can’t even function without you, you big fat hypocrite whom I love.

Best Breakup Line: “I see all my dreams come tumbling down. I won’t be happy without you around.”

18. The Beatles “Yesterday”

Breakup Perspective: I think I really screwed up…

Best Breakup Line: “Why she had to go, I don’t know, she wouldn’t say. I said something wrong, now I long for yesterday.”

17. No Doubt “Don’t Speak”

Breakup Perspective: I know you’re about to break up with me, but please let me delay the inevitable.

Best Breakup Line: “It’s all ending, I’ve gotta stop pretending who we are.”

16. Righteous Brothers “You’ve Lost That Lovin’ Feelin'”

Breakup Perspective: To quote the Temptations: “I know I’m losing you.”

Best Breakup Line: “We had a love, a love, a love you don’t find everyday. So don’t, don’t, don’t, don’t let it slip away.”

15. Justin Timberlake “Cry Me A River”

Breakup Perspective: Boo-effin-hoo.

Best Breakup Line: “Now there’s just no chance for you and me, there’ll never be, and don’t it make you sad about it.”

14. Big Brother & The Holding Company “Piece Of My Heart”

Breakup Perspective: You really hurt me, but c’mon, hurt me again.

Best Breakup Line: “But each time I tell myself that I, well I can’t stand the pain. But when you hold me in your arms, I’ll sing it once again.”

13. Elvis Presley “Heartbreak Hotel”

Breakup Perspective: I’ve checked my broken heart into this metaphoric hotel. Yepp, that’s what you’ve done to me.

Best Breakup Line: “I get so lonely, I could die.”

12. Kelly Clarkson “Since U Been Gone”

Breakup Perspective: My life has been enhanced a great deal since your departure. Deuces!

Best Breakup Line: “You had your chance, you blew it. Out of sight, out of mind.”

11. Beyoncé “Irreplaceable”

Breakup Perspective: You are messing with the wrong bitch.

Best Breakup Line: “I can have another you in a minute. Matter fact, he’ll be here in a minute.”

10. Smokey Robinson & The Miracles “The Tracks Of My Tears”

Breakup Perspective: I’m just walking around with my game face on.

Best Breakup Line: “My smile is my makeup I wear since my breakup with you.”

09. Patsy Cline “Crazy”

Breakup Perspective: Basically, I’m crazy because you’re a tool and I still love you.

Best Breakup Line: “I knew you’d love me as long as you wanted, and then someday you’d leave me for somebody new.”

08. Bill Withers “Ain’t No Sunshine”

Breakup Perspective: My life sucks without her.

Best Breakup Line: “Ain’t no sunshine when she’s gone, and this house just ain’t no home anytime she goes away.”

07. Gloria Gaynor “I Will Survive”

Breakup Perspective: Now that I think about it, I am too damn good for you. So what the hell are you doing back?

Best Breakup Line: “Weren’t you the one who tried to break my with goodbye? You think I’d crumble? You think I’d lay down and die? Oh no, not I.”

06. Sinead O’Connor “Nothing Compares 2 U”

Breakup Perspective: I can’t get over you.

Best Breakup Line: “Nothing can stop these lonely tears from falling. Tell me baby, where did I go wrong?”

05. Adele “Rolling In The Deep”

Breakup Perspective: Did you seriously go and break my heart? Watch the eff out.

Best Breakup Line: “The scars of your love remind me of us, they keep me thinking that we almost had it all.”

04. Dolly Parton (but let’s be honest… Whitney Houston) “I Will Always Love You”

Breakup Perspective: Damnit, I love you, but this is really for the best.

Best Breakup Line: “So goodbye. Please don’t cry. We both know I’m not what you need.”

03. Jackson 5 “I Want You Back”

Breakup Perspective: I took you for granted, and now I’m paying for it. Mulligan?

Best Breakup Line: “Every street you walk on, I leave tear stains on the ground. Following the girl I didn’t even want around.”

02. Fleetwood Mac “Go Your Own Way”

Breakup Perspective: We don’t really seem to be on the same page with this relationship anymore.

Best Breakup Line: “Loving you isn’t the right thing to do. How can I ever change things that I feel?”

01. Alanis Morissette “You Oughta Know”

Breakup Perspective: FYI, you’re a piece of shit, and I genuinely hope your and your bitch new girlfriend are completely (un)happy.

Best Breakup Line: “And every time you speak her name does she know how you told me you’d hold me until you died, til you died? Well you’re still alive.”


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