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From Funny to Tearful – 20 Songs About Breaking Up

There is certainly no shortage of breakup songs—something about music seems to speak to emotion, and a breakup is no exception. Here are our 20 favorites.


Breaking up with someone whom you truly care about is one of the most devastating events that can happen. There is a feeling of life coming to an end. It’s almost as if you are entering a period of mourning, with a similar array of emotions. The human race has an array of different ways of dealing with breaking up, often depending upon the circumstances and the personality of the injured party.
Some of us need to air out our grief, shed a few tears, and lean on a few shoulders. Some of us like to get ourselves back on the horse, declare our intention to live life again no matter who has hurt us, and ride defiantly off into the sunset. Some of us get reflective and nostalgic for better times. Some of us just get downright nasty and vengeful!
20 powerful, emotional breakup songs
The beauty of music is that it can cater to every occasion, to every feeling, and to the peculiarities of every outlook. The following list of 20 songs, although including the typically tearful break up tune, consists of a number of other emotional outpourings that anyone should be able to empathize with and hopefully find some solace in.
#1 “I will survive.” – Gloria Gaynor. This disco classic has been empowering people since the 1970s, encouraging them to throw the chaff of a formerly toxic relationship firmly in the trashcan and move on with their lives. “You’re not welcome anymore!”
#2 “So what.” – Pink. Purportedly elicited by a rather public breakup with a certain celeb *who shall not be named, but whose identity can be Googled fairly swiftly*, this modern breakup anthem is a feisty one-fingered salute to jilters everywhere. Want to pick a fight? This is the song for you. [Read: 33 interesting words for lovers, breakups, and fights]
#3 “I’m so lonesome I could cry.” – Hank Williams. A classic country western tearjerker, they just don’t get any more down-troddenly heart-wrenching than this.
#4 “F**k you.” – Cee Lo Green. This song hit the charts like a thunderbolt a few years back, and unsurprisingly so. What other songs were too shy to say, Cee Lo came out with in a big, whopping bitch-slap for gold diggers everywhere.
#5We are never ever getting back together.” – Taylor Swift. The multiple-time victim of a serial rebound relationship finally grows a backbone and tells the player to take a walk. That’s got to strike a chord with some of us, right? [Read: Rebound relationships and why it’s good for you]
#6 “Unbreak my heart.” – Toni Braxton. This song is so devastatingly sorrowful that I’ve known people in perfectly happy and content relationships to break down into tears after hearing it. It’s quite possibly the saddest-sounding breakup song of all time.
#7 “Survivor.” – Destiny’s Child. This Destiny’s Child classic takes the reins where Gloria Gaynor left off, puts a jet engine on the back, and flies it right up the offender’s ass. These girls are taking no s**t from anyone, with this life-affirming slap in the face to the offenders of unsolicited breakups everywhere.
#8 “Irreplaceable.” – Beyoncé. It seems fitting to follow the previous entry on the list with a Beyoncé song *for obvious reasons*, and the fighting spirit is still evident. Is she going to lie back and bemoan her lot over this particular separation? No way. Beyoncé’s response is simple and equally brutal: “It’s my name that’s on that jag, so come move your bags!” [Read: What should you do after a breakup to feel awesome?]
#9 “Unfinished sympathy.” – Massive Attack. A very, very clever song that matches a hugely powerful and moving score with a haunting and sorrowful melody. If Shakespeare were alive, this would be the kind of song he’d write today.

#10 “Smile.” – Lily Allen. “Smile” is such a lovely, upbeat, happy tune, and Lily Allen is such a sweet and pretty little thing singing it. All the more impact, then, when you realize she’s actually wishing violence and pain upon her former lover—and in such a twisted way, too. If you’re feeling wrathful, this is the song for you. [Read: How to move on and deal with a breakup with a smile]
#11 “Ain’t no sunshine.” – Bill Withers. Withers has a voice to die for and a charm that makes listening to his speech as enjoyable as listening to his music, reaching a collaborative pinnacle of musical excellence in this mesmerizing separation song.
#12 “Mardy bum.” – The Arctic Monkeys. This Brit-indie outfit is renowned for their gritty, real-life observations, and this song is no exception. Although in the process of separation rather than having already broken up, the singer sets the scene in the kitchen, where once-romantic smiles and whispers have turned into grimaces and slanging matches. This song is brilliantly evocative and hinting ever-so-slightly at the hope of a return to better things.
#13 “These boots are made for walking.” – Nancy Sinatra. The original girl power song, the message is clear: you mess with Nancy, you lose Nancy. Simple.
#14 “Piss up a rope.” – Ween. Apparently a southern expression for “go take a hike,” the message is quite plain and to the point: I’m done with you yelling at my friends, taking all my money, and leaving me no smokes, now f**k off! [Read: How to successfully break up with an obsessive lover]
#15 “Don’t speak.” – No doubt. A heartbreaking song that bemoans the breakup at the pivotal moment—the singer begging to be spared the reason, her pain already too much. The fact that this tune totally rocks only adds to the poignancy.
#16 “I hope you’re happy now.” – Elvis Costello. The master of the bitter break up song, Costello outdoes himself this time by poking fun at his ex-lover’s new squeeze—particularly the size of his wedding tackle!
#17 “Part of me.” – Katy Perry. Half a mournful breakup song, half a typical girl-power “up yours” affair, Perry reflects upon how heartbroken she was, whilst flaunting her newfound defiance with some vitriol.
#18 “That phone.” – Grace Potter and the Nocturnals. The power of the clean breakup is explored in this song. Forget regret and the odd slight return, that phone ain’t ever getting answered again! [Read: 25 tips to end a relationship without making it messy]
#19 “Tears dry on their own.” – Amy Winehouse. In typical Winehouse fashion, there is an introverted sadness in this song and an almost gracious attempt to understand her own part in a relationship that failed. Beautiful.
#20 “Cry me a river.” – Justin Timberlake. Arguably possessing the best music video on the list, this song is far from the typical kind of fluff you’d expect from a pop idol. Having found out from the guy she cheated with that his girlfriend has betrayed him, he taunts her for her tears now that he knows. Kind of bitter and a little bit cruel, but you can’t deny that it really is quite satisfying to listen to. [Read: Is it time to break up? – How to read the signs]
However and under whatever circumstances your relationship came to or is coming to an end, there is bound to be a tune from the list above that strikes a chord… in every sense of the word!

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David Cullen
David Cullen
David Cullen is frequently described as erudite, insightful and witty – but only by himself and only after several large glasses of Rioja....