The 25 Best Breakup Songs Ever

28 Feb

Well, here we are. It’s time for the top 25 breakup songs. If you missed the first 25, take a moment to revisit them. If you don’t want to read through them all, I’ll be nice and give you a quick rundown.

50. “I Don’t Ever Wanna See You Again” – Uncle Sam
49. “The Sign” – Ace of Base
48. “Heartless” – Kanye West
47. “Marvin’s Room” – Drake
46. “The One I Love” – R.E.M.
45. “Butterfly” – Mariah Carey
44. “So Sick” – Ne-Yo
43. “Where I Wanna Be” – Donell Jones
42. “Every Breath You Take” – The Police
41. “Free Fallin'” – Tom Petty
40. “Gone” – N*Sync
39. “Nobody Knows” – The Tony Rich Project
38. “We Can’t Be Friends” – Deborah Cox
37. “Pretty Wings” – Maxwell
36. “You Oughta Know” – Alanis Morrisette
35. “Used to Love U” – John Legend
34. “Survivor” – Destiny’s Child
33. “Try Sleeping With a Broken Heart” – Alicia Keys
32. “Burn” – Usher
31. “We’re Not Making Love No More” – Dru Hill
30. “Song Cry” – Jay-Z
29. “Since U Been Gone” – Kelly Clarkson
28. “Back to Black” – Amy Winehouse
27. “Tainted Love” – Soft Cell
26. “Emotional” – Carl Thomas

Gotye25. “Somebody That I Used to Know”  Gotye featuring Kimbra (2011)

I could not get away from this song for seemingly all of fiscal 2012. Somewhere in there, I learned to love it. Somewhere in its quirkiness rested a tragic tale most of us can relate to. The song describes two ex-lovers that can’t be friends. Not only are they not friends, they have nothing to do with each other…they don’t know each other anymore.

Madonna24. “Take a Bow”  Madonna (1994)

Before RiRi told Chris Brown her ex to take a bow a few years ago, Madonna had already told hers to do so…in much bigger and better fashion (seven weeks at #1 on the charts)…in 1994. Hell, she had Babyface singing backup on this. The entire song is a metaphor about a masqueraded relationship that is now over. No one likes having their love taken for granted, and Madonna does what so many of us are afraid to do…”say goodbye.”

BrianMc23. “Anytime” – Brian McKnight (1997)

Confession: I’ve been here. I’ve wondered what an ex is doing. I’ve wondered how she’s doing. I’ve wondered if I ever cross her mind. I’ve since moved on…thankfully. A hauntingly lonely song that mirrors the haunting piano licks that make it so memorable. Brian hasn’t let go of his former lover just yet. He misses her and seems to be holding out hope that she’ll come back to him. Don’t hold on too long, good sir. It’s not healthy.

Gloria22. “I Will Survive” – Gloria Gaynor (1978) 

I’ll probably die still hearing someone singing this song off-key and a crowd of empowered women dancing and singing along word for word…and for some reason loving it. In two lines, this song offers timeless life advice for anyone having trouble moving on: “As long as I know how to love, I know I’ll stay alive / I’ve got all my life to live, I’ve got all my love to give and I’ll survive.” Absolutely perfect.

Lauryn21. “Ex-Factor” – Lauryn Hill (1998)

On again, off again. This track is for that one person we love the most, but hurts us the most. It describes a relationship in which one person keeps trying to leave and whenever he/she does, the other person unsuccessfully tries to fix things. “You let go, and I’ll let go, too…it ain’t workin’.”


BillWithers20. “Ain’t No Sunshine” – Bill Withers (1971)

Yes, Bill, you “ought to leave the young thing alone” if she keeps leaving and not telling you where she’s going or how long she’ll be gone. I know, I know, I know, I know, you know. While Bill Withers is the originator of this classic, have you heard young Michael Jackson blow the lid off of it? Thank me later.


MaryJ19. “Not Gon’ Cry” – Mary J. Blige (1996)

This countdown would’ve lost some credibility if it didn’t feature a song from Waiting to Exhale, right? Blige takes on the persona of a scorned ex-wife who was getting cheated on. She’s not going to cry, though, because he’s not worth the tears. “Ee-lev-uhn years of sacrifice…” *ahem* Sorry, I couldn’t help it.


Dido18. “White Flag” – Dido (2003)

Dido is a ghost of an ex past in this song. She vows to “go down with the ship” (relationship) and to fight until the bitter end. Her poor ex. What’s he supposed to do? She admits that she caused problems in the relationship and doesn’t blame him for moving on, but she hasn’t. She won’t. This song gives credence to the tag, “it’s complicated.”

MJ17. “She’s Out of My Life” – Michael Jackson (1977)

This song represents conflicting emotions post-breakup. Do you laugh or cry? Do you live or die? Do you embrace the freedom of being single or dwell on the past? MJ accepts the blame for taking the relationship for granted for two years, locking his love deep inside and away from her, and his pride getting in the way. Live and learn is the best lesson that one can take away from this song.

JT16. “Cry Me a River” – Justin Timberlake (2002)

Britney Spears left JT in a bad place. This ventilating masterpiece was birthed in that bad place. He loved her, did everything he could for her, but she cheated on him, and destroyed any possibility of a future together. He has cried his tears and dealt with the pain from the breakup and passes it on to her. Vengefully beautiful.


Erykah15. “Tyrone” – Erykah Badu (1997)

We interrupt this countdown of downers and tales of heartbreak to bring you Erykah Badu’s ode to a trifling ex. Tyrone is the friend of the cheap and clueless ex-boyfriend Ms. Badu so eloquently describes in this song. Fellas, this is what can happen when you don’t take care of your woman. Pay attention to your woman. Spend some money on her. Spend some time with her!

NoDoubt14. “Don’t Speak” – No Doubt (1996)

How many songs in the history of music have featured exes on the very song describing their former relationship? Gwen Stefani and Tony Kanal dated for seven years before this song came out and gave the world a glimpse of the fallout. Here, the writing is on the wall and words aren’t even necessary to explain that the relationship has died.

Mayer13. “Slow Dancing in a Burning Room” – John Mayer (2006)

Lonely apart and dangerous together. That’s what I think of when I hear this song. Here’s a toxic relationship that needs to end, but drags on. Both parties know that the relationship is over but both of them are afraid to pull the trigger and officially end it. “Slow dancing in a burning room” or holding on to a dead relationship. Pick your poison.

Guns12. “November Rain” – Guns N’ Roses (1992)

If this was a countdown based on instrumentation alone, put this in the top two. The last two minutes are nothing short of epic. It’s part of a trilogy of heartbreak songs that Guns N’ Roses blessed us with in the 90’s (along with “Don’t Cry” and “Estranged”). This is a song about not wanting to deal with unrequited love. Axl is still very much in love with a woman, but she is no longer in love with him. “Everybody needs some time…on their own.”

Coldplay11. “The Scientist” – Coldplay (2002)

Going back in time is a power some of us wish we had. Chris Martin has messed things up in the relationship, and he wishes to erase it all and start over. He wants to return to a happier time in the relationship when she loved him, and when she was still excited to learn about him. Those days are long gone, but they still haunt him.


Toni10. “Un-Break My Heart” – Toni Braxton (1996)

How do you not feel the pain exuding from this song? Ms. Braxton was dumped by an ex and still wallows in the heartache. She asks this ex to come back, undo the pain that he caused by walking out her life, and replace them with the happy times while he was in her life. The video paints a tragic, dark, and bleak picture as her lover dies in a motorcycle accident, thus leaving her forever. Powerful lyrics. Powerful song.

Boyz9. “End of the Road” – Boyz II Men (1992)

Boyz II Men perfected the art of harmonizing, so sometimes it’s easy to forget that this is a song about a breakup. Denial, really. The relationship is over, but these boyz can’t let go and realize that it’s not “unnatural” for lovers to go their separate ways. I really do miss those mid-song, deep-voice raps, though. Music just isn’t what it used to be.


Isley8. “Voyage to Atlantis” – The Isley Brothers (1977)

What to say about this gem? Hmm…it’s a wonderful deception. Obviously, it’s about a breakup. Ron Isley is selling hopes and dreams. He tells his ex that he’ll always come back to her and that they’ll reunite in a “paradise out beyond the sea” (Atlantis). Newsflash: Atlantis is a mythical place that doesn’t exist. No flames will be rekindled here. Damn, I love this song.

Purple7. “Purple Rain”  Prince (1984)

First off, what is “purple rain?” I’m pretty sure it signifies a girl crying. When she cries, her eyes would “rain” purple mascara. Poetic. Why is she crying? At first, Prince is describing the pain he caused this woman, but he only wanted to make her happy. He didn’t mean for her to fall in love with him. Instead, he just wanted to try and make her happy, but he made her cheat, so he left her behind for her own benefit. Prince, ladies and gentlemen.

Journey6. “Separate Ways (Worlds Apart)”  Journey (1983)

If it’s possible to make a beautiful breakup song, this does it masterfully. Sure, our relationship didn’t work out. Yes, we made promises we couldn’t keep. However, I still love you, you’ll find love somewhere else, and love won’t desert you. Why things don’t work out with the couple isn’t explained, but this song probably wins the award for ending on the most peaceful, loving, unselfish, and heartfelt terms possible.

Adele5. “Someone Like You”  Adele (2011)

“I wish nothing but the best for you…” Much like a lot of songs that have preceded it, Adele’s piece of perfection is performed from the perspective of a jilted lover. What sets this song apart is the fact that she assures herself that she’ll find someone else and harbors no ill will toward her ex. She makes it no secret that she’s not over him, but she puts her pride aside, and only asks to be remembered. Pulchritudinous paradox.

Bonnie4. “I Can’t Make You Love Me” – Bonnie Raitt (1991)

I’ll go ahead and call this the saddest song on this list. Bonnie is in a relationship and deeply in love, but her partner isn’t. She can’t make him love her, and “in these final hours,” she’ll lay down her heart. She doesn’t stop there. In the midst of lying in bed with her lover, she asks for the night to give up the fight of trying to get her lover to reciprocate the feelings she harbors. Impeccably written and performed. My goodness…

Fleetwood3. “Go Your Own Way” – Fleetwood Mac (1976)

Okay, so “Don’t Speak” wasn’t the only breakup song featuring ex-lovers describing their former relationship. Stevie Nicks and Lindsey Buckingham open their world to our world. From the lyrics, Nicks and Buckingham had an on again, off again relationship, but there’s some finality to this song. Here I was at 11 thinking that this song was about Forrest Gump going his own way across the country. It’s so much deeper and better than that.

TheBodyguard2. “I Will Always Love You” – Whitney Houston (1992)

I’m running low on words to describe amazing songs. There isn’t a lot I can say about one of the best selling songs of all time, either. Whitney was at her absolute best here. She made it her song. I know this is a cover, but it is her song. The third verse sums it up perfectly: “I hope life treats you kind. And I hope you have all you’ve dreamed of. And I wish to you joy and happiness. But above all this, I wish you love.”  Bittersweet. Beautiful.

Lynyrd1. “Free Bird” – Lynyrd Skynyrd (1973)

Remember when I said that “November Rain” was instrumentally in the top two of songs on this list? Meet the other one. It features one of, if not, the best guitar solos I’ve ever heard. That’s not the only reason it’s number one, though. “Free Bird” found a way to make a song about a breakup mirror life itself. On the surface, it’s a typical breakup song. He’s breaking things off with the girl. There are places he wants to see and things he wants to do. The deeper meaning behind the song suggests that some birds aren’t meant to be caged. In other words, some people are wild at heart and cannot be changed (tamed).

There are literally thousands of breakup songs. I’ve sifted through my library for three weeks now looking for my favorites and the best. These are my 50. I welcome any songs that I left off, so give me your thoughts/songs/etc.

Oh, and just in case you wanted to hear for yourself what the Top 25 sounds like, I’ve put all together into one playlist which you can enjoy and download here.



Posted by on February 28, 2013 in Countdown, Music, Relationships


Tags: , , ,

3 responses to “The 25 Best Breakup Songs Ever

  1. William

    August 17, 2013 at 11:31 PM

    You have completely overlooked the song ” Was that the Human Thing to Do.” This song was a hit for several different artists, and Its lyrics make it an idle breakup song.


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