Ten Great Break Up Songs

By  Steven Cobb

“Breaking Up is Hard to Do“, bellowed Neil Sedaka back in 1962.

He was right, of course, and while that song has passed the test of time, it didn’t make the cut for this list of ten of the best break-up songs of all time – as if a list of only ten could do justice to the failed relationship, one of the great inspirations in pop music.

Anyway, here we go:

10. Song for the Dumped by Ben Folds Five

This track may be unknown to anyone who didn’t come of age in the late 90s, but it deserves mention. Power-pop trio Ben Folds Five – yeah, there were only three of them – had a handful of minor hits in the 1990s, alternating between warbled ballads like “Brick” and the peppy piano pop of “One Angry Dwarf 200 Solemn Faces”.

On the group’s second album, 1997’s Whatever and Ever Amen, a jilted Folds lashes out on “Song for the Dumped”, an irate anthem aimed at a woman who had the audacity to end their relationship (while presumably keeping his “black t-shirt”).

So you wanted…To take a break…Slow it down some…And have some space…WELL, F*CK YOU TOO!

9. Skinny Love by Bon Iver

Most Bon Iver songs sound appropriate for wallowing in melancholic despair, as Justin Vernon’s achy, orchestral, and often unintelligible vocals fill the air with haunting hints of lament and sorrow. And if you are going to write songs about heartbreaking ends to relationships, one could scarcely prepare better than Vernon did while writing and recording his debut album, For Emma, Forever Ago; he secluded himself in a snowy, winter cabin in Wisconsin and began churning out enchanting folk songs that highlight his soaring falsetto intertwined with intimate and minimalist guitar strums. One of the highlights of the album is “Skinny Love”, a threadbare folk piece where Vernon’s tender tale of a relationship on its last legs subtly tugs at the listener’s heartstrings.

I told you to be patient…I told you to be fine…I told you to be balanced…I told you to be kind…Now all your love is wasted? Then who the hell was I? Now I’m breaking at the britches…And at the end of all your lines…

8. End of the Road – Boyz II Men

No two breakups are exactly alike, and similarly the best breakup songs vary wildly in tone. Some are angry, resentful and vindictive. Others are wistful and anguish-induced. And then there is the variety typified by Boyz II Men’s 1992 super-smash “End of the Road”, where one party refuses to accept the apparent demise of relationship. Through blended four-part harmonies, Boyz II Men’s protagonist alternates between forceful assurances (We belong together…And you know I’m right), utter disbelief (How can you love me and leave…And never say goodbye?), and outright pleading (This time instead just come to my bed…And baby just don’t me go) It’s hardly a lyrical tour-de-force, but the song broke several pop chart records and cemented Boyz II Men’s status as Motown royalty, and still manages to capture the mood of the ditched lover in denial.

7. Babe, I’m Gonna Leave You – Led Zeppelin/Joan Baez

Though the origins of this song were the subject of dispute for many years – it is a folk piece originally penned by Anne Bredon in the late 50s, initially recorded by folk pioneer Joan Baez in 1962, and eventually popularized on Led Zepplin’s 1969 eponymous debut – it is a poignant and powerful tale of a relationship without a future, regardless of who the performer is. The Zeppelin performance is the best-known and most sonically diverse, as the song opens with Jimmy Page’s acoustic plucks amidst Robert Plant’s soft croons that announce his intentions to “ramble” away from his woman, then gradually rises to a heavy rock anthem where Plant’s recurring yelps evoke many of the sentiments that ill-fated romances inspire. Baez’s version, though different, is no slouch, either. Baez’s distinctive high-pitched howls capture the mournful laments of a fleeing lover equal to that of Plant’s shrill screeches.

Hoh, oh God…Miss your lips, sweet baby…It was really, really good…You made me happy every single day…But now I’ve got to go away

6. Someone Like You – Adele

Combine a minimalist piano backdrop with a furiously robust voice and tear-jerking lyrics and you have the makings of a formidable heartbreak song. And that’s probably underselling the power of Adele’s “Someone Like You”. Adele’s Grammy-sweeping second album, 21, is largely centered on a gripping tale of a now-defunct relationship and “Someone Like You” serves as that theme’s centerpiece, as a scorned yet somehow-still-benevolent Adele waves an emotional white flag towards the man she would have preferred to spend the rest of her life with. The sparse production provides Adele’s once-in-a-generation voice with the opportunity to wring every last drip of emotion out of her spoiled relationship. Contrasted with breakup songs that go on the attack, “Someone Like You” weaves a tale of a proud woman doing everything she can to put up a brave face in the midst of overwhelming anguish.

You know how the time flies…Only yesterday was the time of our lives…We were born and raised…In a summer haze…Bound by the surprise of our glory days

5. Ms. Jackson – Outkast

“Ms. Jackson” is a literary device employed by Andre 3000 – one half of the rap duo Outkast – in order to make a sincere expression of remorse towards his estranged “baby’s mama.” Though the lyrics are directed at the mother-in-law figure, the primary purpose is to communicate the competing feelings of sorrow, bitterness and affection that rise out of failed relationships – particularly those with children involved. It may not sound like a breakup song at first, but it truly is a tale of how idyllic young love often is spoiled by the harsh realities of being an adult – and then the aftermath ensues, with complications like custody battles, child support payments, and angry mother-in-laws to contend with. The song is about the failed relationship between Andre 3000 and neo-soul singer Erykah Badu.

King meets queen, then the puppy love thing, together dream…About that crib with the Goodyear swing…On the oak tree, I hope we feel like this forever…Forever, forever, ever, forever, ever? Forever never seems that long until you’re grown.

4. You Oughta Know – Alanis Morrisette

There are many types of breakup songs. Some are sappy. Others full of regret. Many are reflective. And some are angry. And then there is “You Oughta Know”, a vile, rage-fueled screed that catapulted Alanais Morrisette to fame when it was released as the first single from her debut solo album Jagged Little Pill. The intensely vindictive lyrics directed at a former lover endeared the Canadian singer/songwriter to thousands of scorned women worldwide. Employing a lethal voice fueled by raw emotion, Morrisette vocally shoots poison darts at her ex-boyfriend. I doubt any man could feel good about being on the receiving end of the bitter, caustic blows Morrisette delivers in this song. Interestingly enough, there has been rampant speculation about who the intended target of Morrisette’s vindictive bile, with former Full House star Dave Coulier, who dated Alanis in the early 1990s, as the primary suspect – though Morrisette herself has remained mum on who inspired her wrath.

Cause the joke that you laid on the bed that was me…And I’m not gonna fade…As soon as you close your eyes and you know it…And every time I scratch my nails down someone else’s back…I hope you feel it…Well can you feel it.

3. Cold, Cold Heart – Hank Williams

It would be difficult – not to mention foolish – to make a list of the top ten breakup songs without diving into country music, a genre which is often characterized by tales of loneliness and woe. In fact, one could make a pretty solid list solely by country-music legend Hank Williams, with “Your Cheatin’ Heart”, “I’m So Lonesome I Could Cry”, and “Take These Chains from My Heart” near the top. I’m going with “Cold, Cold Heart”, the classic honky-tonk ballad that depicts the frustration that ensues in the face of unreciprocated love. The gloomy song has proven to be so versatile that it has been covered by such music luminaries as Tony Bennett, Louis Armstrong, and more recently, Norah Jones.

There was a time when I believed that you belonged to me…But now I know your heart is shackled to memory…The more I learn to care for you, the more we drift apart…Why can’t I free your doubtful mind and melt your cold, cold heart?

2. I Will Survive – Gloria Gaynor

The ultimate declaration of independence and personal strength in the wake of a life-altering breakup, disco diva Gloria Gaynor’s “I Will Survive” celebrates the wonderful sense of individual empowerment that comes when one has finished licking wounds and is ready to move forward. The number-one hit from 1979 features Gaynor’s sassy and triumphant vocals over simple disco beats, “I Will Survive” is an ode to resiliency, providing an instructive lesson that proves that on the other end of the grieving process, there emerges a rekindled spirit, often better than before. For a breakup song, that’s a tough message to top. Also a shout out to the cover by ‘90s alternative outfit Cake.

Go on now, go, walk out the door…Just turn around now cause you’re no welcome anymore…Weren’t you the one, who tried to break with goodbye…Did you think I’d crumble? Did you think I’d lay down and die?

1. Don’t Think Twice It’s All Right – Bob Dylan

The most prolific singer/songwriter in American History, Bob Dylan recorded “Don’t Think Twice It’s All Right” for 1963’s The Freewheelin’ Bob Dylan, years before he became a cultural icon and worldwide megastar. The song is signature Dylan: simple yet richly melodic, with lyrics that are refined enough to convey a wide array of emotions. As far as breakup songs go, “Don’t Think Twice It’s Alright” provides a little bit for everyone: it’s a pretty song that tenderly laments a doomed relationship, while at the same time providing hope for a better future. Finally, the song provides some subtle, yet unmistakable, barbs at his former lover. For someone in the midst of a difficult breakup, few experiences could be more cathartic than listening to this classic American folk song on repeat for a couple hours.

So long, honey, baby…Where I’m bound, I can’t tell…Goodbye’s too good a word, babe…So I’ll just say ‘fare thee well’…I aint sayin’ you treated me unkind…You could of done better, but I don’t mind…You just kind of wasted my precious time…But don’t think twice, it’s alright.

Steven Cobb is a professional web developer and an amateur dating coach who is passionate about helping men and women find their perfect match. He lives in the Bay Area with his family. Among his current projects is online publishing for DatingMoxie.com, a website that reviews and analyzes the biggest brand names in online dating.