Now that Valentine’s Day is over and love has faded away like smoke from the air, let’s get down to the nitty gritty. For every action, there is an equal and opposite reaction. For every loving relationship, there is an equal and opposite failed relationship. This list is for the brokenhearted and heart breakers. This list is for those who are fixated on an old flame and for those who extinguished what used to be a burning flame. No disclaimer will be necessary on this one unless you can’t handle a list full of raw emotion. Actually there is a disclaimer.
Disclaimer: Taylor Swift did not make it onto this list.
50. “I Don’t Ever Want To See You Again” – Uncle Sam (1997)
Talk about a downer of a song. Not only is the love of Uncle Sam’s life cheating on him, she’s cheating on him with his best friend. Uncle Sam takes correct and proper action by moving on and vowing to never see her again. Let’s hope he doesn’t want to see his best friend again, either.
49. “The Sign” – Ace of Base (1993)
While most of Ace of Base’s songs sound alike, this one stands out. Maybe it’s because the album is called The Sign, too. Maybe it’s because of the fact that it packs quite a punch beneath the upbeat, 90’s, Euro-pop sound. This is a song about growth. It’s about seeing a former lover after a significant amount of time apart and wondering why the hell you dated that person in the first place.
48. “Heartless” – Kanye West (2008)
I could put the vast majority of 808s and Heartbreak on this list, but I’ll stick with this song. I won’t speculate as to who the muse of this song was (even though it’s not hard to figure out), but it’s pretty apparent that she hurt Kanye pretty badly. Hell, the guy went from rapper to auto-tune singer because of her. Judging by the lyrics, there was no closure or resolution after the relationship ended as he “left it wrong” and she couldn’t “make it right”.
47. “Marvin’s Room” – Drake (2011)
I was extremely tempted to put JoJo’s version of this song at this spot, but it just felt disrespectful. Drake made this a hit. Okay, we’ve all done it. Drunk dialed or sent a drunk text to an ex. It probably didn’t end well, either. Here, the ex has moved on to someone else, but Drake is bitter. He has resorted to surrounding himself with females and burying his sorrows in the bottle, but hey, “[he’s] just sayin’ [she] could do better.”
46. “The One I Love” – R.E.M. (1987)
I love this song. It’s twisted, evil, and awful, but it has a certain charm to it. It sounds like a love song. The title makes you think it’s a love song. It’s not. It’s about a girl (really, more than one) that the singer once “loved” and left behind. She turns out to be a “simple prop to occupy [his] time.” Never has the concept of “love ’em and leave ’em” sounded so…good.
45. “Butterfly” – Mariah Carey (1997)
Breaking up is never fun, and it usually hurts a great deal, but some songs make it easier to cope. This is one of those songs. Mariah Carey lets her lover go to “spread [his] wings and prepare to fly”. Whether it’s because of a job, to follow his dreams, or some mixture of the two, she lets him go in hopes that he will one day return to her. Beautiful song.
44. “So Sick” – Ne-Yo (2006)
A lot of times, when a relationship ends, old habits must end with it. Ne-Yo sings of changing the answering machine, fixing the calendar marked with an anniversary, being done with wishing his girlfriend was there, and not listening to “stupid love songs” anymore. He soon discovers that these things are not the easiest things to do.
43. “Where I Wanna Be” – Donell Jones (2000)
Mr. Jones is forthright and honest when he tells his girl that he’d “rather leave than to cheat.” Basically, his playing days aren’t over yet. He’s been with this woman for years, and he wants to see what else is out there before he settles down. Donell Jones made a hell of a song about a hell of a decision to leave.
42. “Every Breath You Take” – The Police (1983)
File this one away in your “Creepy Classics” folder. People have different ways of dealing with break-ups. Some cry, some drink, some reflect. Sting stalks. He wants his ex back, but he goes about it all wrong. I hate when people misinterpret this song. It’s not sweet. It’s not protective. It’s not cute. It’s disturbing. While it’s a great song, do your family, friends, and guests at your wedding reception a favor and refrain from having this song played.
For such a sweet-sounding and freedom-seeking song, this one starts off pretty damn icy. Here’s a guy who has a great girlfriend. He wants to be free, though. He leaves her in the suburbs of L.A. with a broken heart to pursue his freedom and independence. At first, he doesn’t even miss her, but after his days of being a “bad boy,” he realizes how empty it feels and how much he misses her.
40. “Gone” – ‘N Sync (2001)
“Bye, Bye, Bye” could have gone here, but I think “Gone” is for this list. Justin and his backups aren’t quite sure where Justin’s girl went. They don’t even know why she went wherever she went. Maybe it was something he said. Maybe he was too blind to see the warning signs. “The truth remains [she’s] gone,” and he’s miserable. He vows to “hang around and find some things to do to get [his] mind off missing [her].” Good luck with that.
39. “Nobody Knows” – The Tony Rich Project (1996)
I swore up and down that this was Babyface when I first heard it in the fifth grade. Turns out it was a one hit wonder. Here’s a song that outlines what can happen when you keep your emotions hidden and don’t fully appreciate what you have while you have it. Lonely nights, sad days, and thinking about a love gone wrong. He’s going to go find his ex-lover and tell her what he should have told her a long time ago, though. Once again, good luck with that.
38. “We Can’t Be Friends” – Deborah Cox featuring R.L. (1999)
I love songs that can put new spins on break-ups. Here we have a former couple that realizes that they can’t go from lovers to merely friends because they’re still in love with each other. That “let’s just be friends” quip doesn’t always fly, and here is one of those instances. Beautifully crafted.
37. “Pretty Wings” – Maxwell (2009)
I used to always have to remind myself that this song was about a break-up. It’s called “Pretty Wings”. You’d think this song was about a happier subject than two lovers going their separate ways. She wronged him. He wronged her. These facts almost get lost in the mystique of Maxwell’s voice.
36. “You Oughta Know” – Alanis Morissette (1995)
This is that raw, unadulterated, and bitterly sarcastic, final haymaker thrown by a jilted lover. Another woman has entered the picture, and Alanis perfectly captures what it feels like to be replaced by someone who isn’t nearly as good, selfless, or freaky as she is. And when she scratches her nails down someone else’s back, she hopes her ex feels it. Read between the lines. Bold. Brash. Brazen.
35. “Used to Love U” – John Legend (2004)
Loving someone with all you have and realizing that that’s not enough. That’s this song in an eggshell. Everyone has their limits, and Mr. Legend reached those limits here. No one likes being unappreciated and taken advantage of, and this song serves as an anthemic declaration of empowerment. “You’ll miss me when I’m gone” rings so loudly.
Honestly, this song would be a little bit higher if it wasn’t for Michelle’s verse. Sorry, I’m just being honest. I still really like this song, though. It’s a female anthem that doesn’t bash the ex-boyfriend in the process. They’re better than that. They wish him the best, hope he’s blessed, and that he finds happiness. Well done, ladies.
33. “Try Sleeping With a Broken Heart” – Alicia Keys (2009)
This song expresses that harsh reality of heartbreak perfectly. If you’re going through sleepless nights thinking about that ex-lover, this song is for you. If you’re struggling with those feelings that are still there after the relationship is over, this song is for you. If you’re not going to let said break-up destroy you, this song is for you. Alicia Keys caught lightning in a bottle by making this song sad and uplifting at the same time.
32. “Burn” – Usher (2004)
So succinct. So direct. So painful. So good. Usher actually lays out how to break up with a significant other when the relationship has reached its end. It’s “been a long time coming,” and it will hurt, but it must be done. Great song and a great album.
31. “We’re Not Making Love No More” – Dru Hill (1997)
Dru Hill takes us into the bedroom, but in a depressing way. The relationship has fallen apart and these lovers are moving further apart every day. They don’t talk anymore, they used to be best friends, and well, they’re not having sex anymore. “How did it slip away?” You’ve given us a laundry list of reasons. Which one do you want? In my mind, this is a song that represents the very last moment before the actual break-up.
30. “Song Cry” – Jay-Z (2002)
Every now and then, you find a song from a dude you wouldn’t expect to show his vulnerable side. This time, that song comes from one, Shawn Carter, better known as Jay-Z. Jigga was in his feelings on this song, but what a great song it turned out to be. Most guys have that one ex-girlfriend that they regret screwing over. Many of those guys still find themselves reminiscing over her from time to time. Thanks for this one, Jay.
29. “Since U Been Gone” – Kelly Clarkson (2004)
Freedom. That’s the word that comes to mind when I hear this song. When you’re out of a relationship that was going nowhere, you can breathe again. You can move on. You can walk into your ex-boyfriend’s house and destroy everything. I really hope people didn’t get any funny ideas from this video.
28. “Back to Black” – Amy Winehouse (2006)
Sometimes after a relationship ends, people go back to something comfortable for them. In this instance, Amy Winehouse goes back to drinking and smoking while her ex goes “back to her” (his ex). I never said there wouldn’t be dark songs on this list. This is one of them.
27. “Tainted Love” – Soft Cell (1981)
Sing it if you know it. *ahem* “Sometimes…I feel I’ve got to *clap* *clap* run away….I’ve got to *clap* *clap* get away…” While the credit goes to Gloria Jones’ original, Soft Cell made it the catchy, karaoke special that it has become. The meaning of this song is simple. A guy has had enough of his girlfriend and her “tainted love”, so he tells her that he’s packing his things, leaving, and not to touch him. *clap* *clap* Good decision.
26. “Emotional” – Carl Thomas (2000)
Sting keeps finding multiple ways to get onto my countdowns. Here, he lends Carl Thomas the music from “Shape of My Heart,” and Thomas makes the most of it. We’re presented with another relationship that has fallen apart. When you find yourselves spending more time fighting for a relationship than actually having one, then maybe it’s time to call it quits. That’s exactly what Carl Thomas does. It hurts, but “the love is through.”
Stay tuned for the top 25 coming very soon…