The Saddest Breakup Songs Of All Time

The Ronettes had it all wrong. The best part of breaking up is not the making up. That rarely happens, and when it does, it often leads to more breaking up. No. What you really need is a deliciously painful breakup anthem.

Generations of musicians have written songs to soundtrack this low moment in our lives that is almost as inevitable as death and taxes. Our parents had Elvis and Gordon Lightfoot. We've got Adele, Ed Sheeran, Taylor Swift and Sam Smith. What follows – in our humble, many times heartbroken opinion – are the finest, saddest breakup songs of all time. Play ‘em just loud enough to drown out the sobbing.

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"Don't Look Back in Anger" by Oasis

It's a breakup song to phases in life.
"The First Cut is the Deepest," Sheryl Crow (or Cat Stevens)

Here's the question this song poses. After experiencing heartbreak, is it possible to love again with the same unabashed enthusiasm?
"Un-break My Heart," Toni Braxton

In which Toni invents an entirely new verb.
"White Horse" by Taylor Swift

OG Taylor was all about the heartbreak ballads. "White Horse" is about that moment when you realise that you've been played for a fool and you gotta get out of dodge sharpish. Sadly, not all fairytales can come true.
"Too Much To Ask" by Niall Horan

Niall is the third member of One Direction to release a solo album and, predictably, it's already been a huge smash in the UK, as well as across the pond. Flicker's third single, "Too Much To Ask" is the most heart-shattering cut from the record. Tissues at the ready.
"Too Good At Goodbyes" by Sam Smith

Poor Sam Smith and his perpetually bleeding heart (or maybe not anymore) will lend you a shoulder to cry on.
"I Miss You" by Clean Bandit & Julia Michaels

Clean Bandit have become pretty well known for their uplifting anthems like "Rockabye" and "Symphony", but their latest offering sees the British band taking a more sombre note with the help of "Issues" hitmaker Julia Michaels.
Image: Courtesy of Mercury.
"I'm Not in Love" by 10cc

Easily one of the most melancholy love songs ever written, this 1975 hit was inspired by band member Eric Stewart's wife's claim that he didn't profess his love enough. Ultimately, its tone of painfully obvious defiance and denial is excruciating for anyone trying to convince themselves that they're over a breakup.
Photo: Courtesy of Island.
"Teardrops" by Womack & Womack

Think of this karaoke favourite as a crying-in-the-club precursor to Robyn's heartbreak anthem "Dancing on My Own." Ironically, the duo behind it, songwriters Linda and the late Cecil Womack, were married in real life.
"Careful You" by TV On The Radio

Lyrics like "I know it’s best to say goodbye/But I can’t seem to move away" perfectly capture the discord between the head and the heart. Are imperfect partnerships worth trying to fix? When do you throw in the towel? Isn't being responsible such a cock-blocker?
Image: Courtesy of Interscope Records.
"Maps" by Yeah Yeah Yeahs

Frontwoman Karen O. channeled the emotional torment of her real-life relationship with then-boyfriend Angus Andrews into this determined but damaged plea.
Image: Warner Bros./Reprise.
"Silver Springs" by Fleetwood Mac

If anyone knows a thing or two about romantic bust-ups, it's Fleetwood Mac. Stevie Nicks wrote this melancholy ballad about trying to forget an ex who has found new love in response to her split from Lindsey Buckingham. It fittingly appeared as a B-side on his breakup single, "Go Your Own Way", but didn't land on an album until the band's reunion album two decades later.
Image: Courtesy of Interscope.
"Apologise" by OneRepublic

OneRepublic frontman Ryan Tedder has done a brisk trade in breakup ballads, penning Leona Lewis' "Bleeding Love" and this piano-driven hit from 2006. Timbaland's R&B remix helped propel the track to the top of the charts, giving voice to lovelorn listeners sick of dishing out second chances.
Image: Courtesy of Polydor Records.
"It's Not Over Yet" by Klaxons

This cover of Grace's "Not Over Yet" is a total banger for anyone not reeling from a painful split.
Image: Courtesy of Merge/Rough Trade.
"Crown of Love" by Arcade Fire

Win Butler and Régine Chassagne may be one of rock's reigning couples, but they also know that breakups are shitty. This chorus is crushing:

"If you still want me, please forgive me,
The crown of love has fallen from me.
If you still want me, please forgive me,
Because the spark is not within me."
Image: Courtesy of Atlantic.
"Against All Odds (Take A Look At Me Now)" by Phil Collins

Just because it's cheesy doesn't make it true. Phil Collins' divorce from his first wife inspired this power ballad about a man who hopes against hope that a reconciliation is possible. (The song was used in the 1984 film Against All Odds, in case you were wondering what a shirtless Jeff Bridges had to do with all this.)
Image: Courtesy of Columbia.
"Always On My Mind" by Willie Nelson

Peggy Lee, Elvis Presley, Willie Nelson, and the Pet Shop Boys all famously recorded their own versions of this wistful ballad, but none of them actually wrote it; credit goes to songwriters Johnny Christopher, Mark James, and Wayne Carson. Nelson's 1982 take won a Grammy, though we're just as fond of (and likely to avoid during times of heartache) Pet Shop Boys' dance-y update.
Image: Courtesy of Konichiwa.
"With Every Heartbeat" by Robyn and Kleerup

Long before Lena Dunham and Allison Williams shimmied to "Dancing On My Own," those in the know turned to this track about resolving to move on after a split even though you still wish it would miraculously work out. It's perfect for a boogie, or a breakdown, depending on your mood.
Image: Courtesy of Reprise.
"The Last Time I Saw Richard" by Joni Mitchell

Always adept at channeling wistfulness and melancholy, Mitchell here croons about an old lover who went on to marry a figure skater while she's "got nothing to talk to anybody about."
Image: Courtesy of Lava/Republic.
"Liability" by Lorde

Produced with Bleachers rocker Jack Antonoff, "Liability" is the second single off Melodrama and continues the breakup theme initiated by "Green Light." Instead of a dance-y track, however, the New Zealand singer delivers a more mournful piano ballad, which really lets the sadness and regret creep in.
Image: Courtesy of Arista.
"White Flag" by Dido

When they say it's over but you're just not ready to give up. Girl, we have been there. Dido, incidentally, wrote this about one of her own past relationships.
Image: Courtesy of Columbia.
"If You Leave Me Now" by Chicago

This 1976 soft rock classic is schmaltzy until you hear it mid-breakup, when Peter Cetera's plaintive cry for his lover to "please don't go" suddenly become painfully profound and heartbreaking.
Image: Courtesy of Sussex Records.
"Ain't No Sunshine" by Bill Withers

When Hugh Grant is pumped up, he bounces around to the Pointer Sisters. When he's heartbroken, he mopes around Notting Hill listening to this.
Image: Courtesy of 4AD Records.
"Seasons (Waiting On You)" by Future Islands

"I've grown tired of trying to change for you" gets us every.single.time. So wistful, so true, so relatable.
Image: Courtesy of Reprise Records.
"Wicked Game" by Chris Isaak

Everyone remembers the sultry video, but if you take Helena Christensen out of the equation you're left with a melancholy ballad about longing for someone who did you and your heart wrong. "What a wicked thing to say, you never felt this way"? Helena's got some explaining to do.
Photo: Courtesy of Reprise.
"If You Could Read My Mind" by Gordon Lightfoot

Reaching number one in the Canadian music charts in 1970, this must be the most underrated song about heartbreak. Lightfoot wrote it one summer in a house, thinking about his divorce. It is, no doubt, a lyrical masterpiece:

"I never thought I could act this way
And I've got to say that I just don't get it
I don't know where we went wrong
But the feeling's gone and I just can't get it back."
Photo: Courtesy of Sub Pop/DGC.
"Where Did You Sleep Last Night" by Nirvana

Let your heart rip as Kurt Cobain screams "My girl, my girl, don't lie to me, Tell me where did you sleep last night" in this iconic unplugged cover from 1994. In the documentary about his life, Kurt Cobain: Montage Of Heck, it is implied that he's singing about his wife, Courtney Love, having believed at the time that she cheated on him.
Photo: Courtesy of RCA Victor.
“The End Of The World” by Skeeter Davis

"Don't they know it's the end of the world
'Cause you don't love me any more."

Oh, the ache. This country song was recorded in 1962 and enjoyed huge chart success in the U.S. It was covered countless times, by big-time bands such as the Carpenters, and formed part of the soundtrack to the film Girl Interrupted. Let that vinyl crackle break your heart.
Photo: Courtesy of RCA Victor.
"You've Lost That Lovin' Feeling" by Elvis

It's easy to dismiss Elvis' songs as overplayed pop anthems, but if do, then you miss everything. Originally recorded by The Righteous Brothers in 1954, Elvis first boomed out his cover in 1970. He separated from his wife Priscilla two years later, and, well, that definitely adds to the heartbreak we hear when we listen back now.
Photo: Courtesy of Columbia.
"Lilac Wine" by Jeff Buckley

Hands down one of the most beautiful songs ever recorded. Originally written by James Shelton (who?) "Lilac Wine" is about getting drunk and remembering the one you love without the painful sober reality that they are the one you lost.
Photo: Courtesy of EMI/Food Records.
"No Distance Left To Run" by Blur

Damon Albarn wrote this slow, incurably sad song about his split from fellow musician Justine Frischmann in 1999. “It upset me, that song. It upset me singing it”, is the quote that accompanies every mention of the track.

If this hits the spot, move on to “Tender”, another track from the album, about the same thing.
Photo: Courtesy of Elektra.
“Pictures of You” by The Cure

Robert Smith has been writing intensely personal, moody songs of heartbreak pretty much since he founded The Cure in 1976. But this one is the most beautiful. Almost eight minutes long, "Pictures of You" finds Smith reflecting on memories of a person he loved, triggered by old photographs. “Remembering you falling into my arms / Crying for the death of your heart / You were stone white, so delicate, lost in the cold,” he sings. “You were always so lost in the dark.” For a Goth boy who is still married to his high school sweetheart, he sure knows how to capture the pain of lost love.
Photo: Courtesy of Interscope.
“Don’t Speak” by No Doubt

Success must have been bittersweet for Gwen Stefani and Tony Kanal, punk-ska’s answer to Stevie Nicks and Lindsey Buckingham. No Doubt’s breakthrough 1996 single (and lone No. 1) is all about their breakup — an emotional earthquake Gwen clearly hadn’t recovered from the day she cut this vocal.
"Shiver" by Lucy Rose

We first got wind of Rose's sweetly melancholy tune when it was played during the Adam-Hannah split in season 4 of Girls. Since then, it's been a go-to for when we're feeling weepy. Rose doesn't place the blame on her romantic partner for the split; she admits responsibility. But even though the breakup was mutual, she remains nostalgic for the good moments.
Photo: Courtesy of Warner Bros. Records.
"A Case Of You" by Joni Mitchell

Joni Mitchell's conversational, devastating song, describes what it's like when a relationship is over but a connection to another person remains. "You're in my blood like holy wine/ You taste so bitter and so sweet," she sings. There are plenty of songs on Blue that will do the trick if you're looking to wallow, but "A Case Of You" articulates what it's like to a lose someone who has burrowed into your soul.
Photo: Courtesy of Parlophone.
“Nothing Compares 2 U” by Sinead O’Connor

If you know the exact amount of time that’s elapsed since you got dumped, you’re in deep trouble. On this Prince-penned classic, we meet Sinead “seven hours and 15 days” after her love took a hike, and she’s still reeling. She’s even been to the see the doctor. Doc's advice: Have some fun.
Photo: Courtesy of XL Recordings/Columbia.
“Someone Like You” by Adele

There’s a war going down inside Adele’s head. She wants her ex to be happy, and yet she finds herself wandering past his flat, hoping he’ll see her, remember the good times, and forget all about his new girl, who happens to be his wife. “Never mind, I’ll find someone like you,” she sings, though she, like Sinead, knows that nothing compares.
Photo: Courtesy of Sony.
“Love Is Stronger Than Pride” by Sade

While Sade wishes she could hate this guy who's wrecked her life, the affection she feels is quick and tenacious.
Photo: Courtesy of Arista.
“Don’t Turn Around” by Ace of Base

Typically, neither crossover reggae hits nor songs by Swedish pop foursomes are known for being particularly sad. (When was the last time Sublime or Abba made you bawl?) For whatever reason, though, this moody summer jam — all about keeping a brave face while having your heart ripped out — has less bounce than a punctured beach ball.
Photo: Courtesy of Capitol.
“I Can’t Make You Love Me” by Bonnie Raitt

Is it a breakup song if the people in question are still sharing a bed? In this all-time soul-crusher, the intimacy is purely physical, and as unfulfilling as that is, Bonnie will take it — for a little bit longer. “Morning will come and I'll do what's right / Just give me till then to give up this fight,” she sings, working up the strength to walk away. “And I will give up this fight.”
Photo: Courtesy of EMI.
“It Must Have Been Love” by Roxette

Immortalized in Pretty Woman, “It Must Have Been Love” represents the perfect ratio of schlock to sentiment. In someone like Celine Dion’s hands, this would have been a complete disaster, but the Swedish duo of Marie Fredriksson and Per Gessle gaze off to “where the water flows” and “where the wind blows” without sounding like ‘90s Disney characters.
Photo: Courtesy of Roc-a-Fella Records.
“Song Cry” by Jay-Z

Rappers have feelings, too. The thing about Jay is that he has trouble showing his, so in lieu of shedding actual tears, he aims to “make this song cry.” He does a decent job, though even as he opens his heart and apologizes to the girl he cheated on, he doesn’t quite ditch the macho posturing that might have made this tender mea culpa ring truer.
Photo: Courtesy of WAX TIME.
“Crying” by Roy Orbison

There’s nothing worse than bumping into your ex and having to pretend you’re not a total whimpering mess. Roy figures he pulls it off — “You couldn’t tell that I’d been crying” — and if he does, he’s a hell of an actor. In that signature opera-billy style of his, Orbison sings with a hurt not easily hidden.
Photo: Courtesy of Capitol.
“Caroline, No” by The Beach Boys

Originally titled “Carol, I Know,” this song became infinitely better when Brian Wilson misunderstood collaborator Tony Asher’s initial reading of the lyrics. The narrator in this song doesn’t know Jack. “Where did your long hair go?” he asks. “Where is the girl I used to know?” “Could I ever find in you again things that made me love you so much then?” If the bummed-out orch-pop backing is any indication, the answers to that last question is “Brian, no.”
Photo: Courtesy of Capitol.
“You’ve Got to Hide Your Love Away” by The Beatles

Everyone tells John Lennon he should suppress his feelings and go about his business, but this guy’s business was expressing his feelings. They come through in a big way on this transitional Beatles cut.
Photo: Courtesy of Interscope.
“Lost Cause” by Beck

Arguably the saddest song on Beck’s saddest album, this is the slow, strummy equivalent of waving a white flag. Poor Beck knows there’s nothing he can do to save this girl from herself, so he’s pulling his forces and signing whatever treaty he needs in order to escape with his sanity.
Photo: Courtesy of Geffen.
“Stay” by Lisa Loeb

Everyone’s favorite bespectacled over-thinker hit on something universal with the line, “I think that I’m throwing, but I’m thrown.” That’s what it’s like being in a bad relationship. The question of “should I stay or should I go?” isn’t always a binary yes-no kind of thing. Sometimes, it sends you down the kind of emotional rabbit hole Loeb goes into here, with winning results.
Photo: Courtesy of Sub-Pop Records.
“Nothing Better” by The Postal Service

Selective memory is a the worst. The male character in this synth-pop duet figures there’d be nothing sweeter than marrying the girl who’s recently left him. Unfortunately, she’s prepared charts and graphs to remind him of why the good times weren’t that good. This is young love in the time of Excel.
Photo: Courtesy of Columbia.
“You Left Me Standing In the Doorway” by Bob Dylan

Dylan waited until he was 56 to write one of the best lines of his career: “Don’t know if I saw you, if I would kiss you or kill you.” That, like the title, pretty much says it all, but then he goes one better: “It probably wouldn’t matter to you anyhow.” It’s a rascally line from a guy who’s wicked bummed but still pretty feisty.
Photo: Courtesy of Virgin Records.
“The Heart Remains A Child” by Everything But the Girl

In this song, vocalist Tracey Thorn bluntly asks a question that occurs too often during heartbreak: "Why don't you love me?" If that seems like a simplistic inquiry, well, that's sort of the point. This song perfectly expresses how we regress after heartbreak, and fall into our same, mopey patterns.
Photo: Courtesy of ISLAND-DEF JAM.
“Stay” by Rihanna ft. Mikky Ekko

Rih clears a little path through a hoarder’s den of messy feelings on this confusing piano ballad. “Not really sure how I feel about it,” she confesses, right before her duet partner, Mikky Ekko, sings the same line. These are two people who are completely wrong for each other, and when they join their voices on the line “funny, you’re the broken one, but I’m the only one who needed saving,” it’s like they’re both dishing blame and seeking salvation at the same time.
Photo: Courtesy of Virgin Records.
“Again” by Janet Jackson

When Janet hears her former boo is back in town, she goes off on a soul-searching journey that begins with wishful thinking (“I’ll never fall in love with you again”) and ends with acceptance (“God knows I do love you again”). The single-word title may be a predictor of how this story ends.
Photo: Courtesy of Hip-O Records.
“Almost Blue” by Elvis Costello

“There’s a girl here and she’s almost you,” Elvis sings, weary like a lounge singer playing to a roomful of 2 a.m. drunks. He’s found a new romance that leaves him a little cold — “almost blue” — and that makes for one chilly-ass torch song.
Photo: Courtesy of Roc-A-Fella Records.
“Heartless” by Kanye West

At the risk of being melodramatic, Kanye dubs this “the coldest story ever told.” It’s the tale of two former lovers — presumably Yeezy and former fiancée, Alexis Phifer — who’ve wronged each other and wound up bitter enemies. “How could you be so Dr. Evil?” he raps, too mentally spent to muster anything better than an Austin Powers joke.
Photo: Courtesy of Atlantic.
“You Were Meant for Me” by Jewel

If you ask Parks and Recreation protagonist Leslie Knope, there are few problems that can’t be solved by breakfast foods. Jewel might beg to differ. “I got my eggs, I got my pancakes too / I got my maple syrup, everything but you,” she sings, unwilling to accept her sugary a.m. feast as a substitute for the one that got away. Eventually, Jewel tells herself, he’ll realize they’re meant for each other. Until then, Mrs. Butterworth will have to pick up the slack.
Photo: Courtesy of Geffen.
"The World Has Turned and Left Me Here” by Weezer

Rivers Cuomo has it even worse than Robert Smith does in “Pictures of You.” On this Blue Album gem, the Weezer frontman is talking to wallet photos and losing his grip on reality. “You laughed, enchanted by my intellect,” he sings to his ex. “Or maybe you didn't.” Either way, he won’t be adding any more smiley snapshots of this girl to his plastic sheath.
Photo: Courtesy of Sony Music Entertainment.
“I Will Always Love You” by Whitney Houston

That towering, thunderous, ground-shaking “And I…” high note Whitney hits toward the end of this monster ballad makes total sense. Written by Dolly Parton, this is one of the most selfless love songs of all time, and before taking her leave of the man she knows she’s holding back, Whitney gets in one last show of dignity: an extended vowel sound people will be talking about until the end of time.
Photo: Courtesy of Sony.
“It’s Too Late” by Carole King

It’s the sense of finality that makes this 1971 chart-topper such a killer. “Something inside has died, and I can’t hide it,” King sings, a little sad, a little relieved to no longer have to carry on a charade. “And I just can’t fake it.”
Photo: Courtesy of RCA.
“Are You Lonesome Tonight” by Elvis Presley

In the famous spoken-word part, a truly miserable-sounding Elvis looks back on a failed relationship like a theater critic reviewing a play. Act one was great. Act two: not so much. Looking ahead to the act three, Elvis is only willing to entertain one possible ending. “If you won't come back to me,” he says, “then make them bring the curtain down.”
Photo: Courtesy of Sony.
“Without You” by Mariah Carey

Talk about fresh wounds. “I can’t forget this evening, or your face as you were leaving,” sings Mariah, who’s coming to us mere hours after the breakup went down. She hasn’t had time to process things, so she’s feeling a little overdramatic. Hence that chorus: a show-stopping declaration of why life is no longer livable. In time, she’ll get over it, but for now, let her wail.
Photo: Courtesy of Universal Republic.
“Back to Black” by Amy Winehouse

The references to “puff” and “blow” give this an air of druggy self-destruction that heightens the sadness, especially in light of Amy’s untimely death. Even without those lines, though, it’s a heavy song — a smoldering James Bond theme for an everyday story about a woman plummeting into darkness as her man goes back to his former girlfriend.
Photo: Courtesy of Sire/London/Rhino.
"Take a Bow" by Madonna

Taking a page out of the King's playbook, Madonna uses theater as a metaphor for her latest heartbreak. "You deserve an award for the role that you played," she tells the deceptive lover she's finally wriggled free from. "No more masquerade." Given that Madge used to be married to Sean Penn, the lesson here may be to only date crummy actors. Their lies are easier to spot.
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