“Breaking up is hard to do” sang Neil Sedaka in 1962—a chirpy understatement that sets the tone for our roundup of the best breakup songs of all time.
Yes, breaking up is hard to do—so hard, in fact, that a good chunk of the finest pop music ever produced has sprung from its well of agony. But as tough as it is to dump or be dumped, when you find the right soundtrack to your suffering it can also feel weirdly enjoyable—as tracks by such pop poets as Alanis Morissette, Kanye and expletive king, Cee Lo Green attest.
So we invite you to celebrate the heartbreak—whether angry, homicidal or just a bit sad—with our collection of the best breakup songs ever recorded. Hurts so good, don’t it? And if you’re done with wallowing and want a pick-me-up, consult our lists of the ultimate happy songs instead.
Talk about heartbreak. On this stunner off 1968’s Tell Mama, James claims she’d prefer never being able to see again than watch her love walk away. What’s more, she’s helpless: She notices the way her man is chatting up another girl and knows right then and there that, no matter how much she cares for him, it’s all over. Throw that sentiment over a simple chord progression that builds beautifully with horns, an organ, backing vocals and a heart-melting performance by James, and you've reached timeless soul perfection.
2. “Nothing Compares 2 U” by Sinead O’Connor
Originally written and composed by Prince, “Nothing Compares 2 U” didn’t reach iconic, heart-decimating status until a certain headstrong Irish singer-songwriter tried her hand—and those sad, sad eyes—at covering it in 1990. The video, which alternates between a stark close-up of O’Connor’s despair-wrought face and shots of the dark-cloaked songstress roaming through Paris's Parc de Saint-Cloud, was cited by Miley Cyrus as the inspiration for her 2013 “Wrecking Ball” video. It can’t be denied that three decades later, O’Connor’s wrenching rendition still packs a punch.
3. “Somebody That I Used to Know” by Elliott Smith
The late-great Smith might have sung, “So when I go home, I'll be happy to go / You're just somebody that I used to know,” but he wasn’t fooling anyone: This bare-bones, beautiful track is all about full-on heartache, albeit of the dismissive, fuck-you-I’m-fine variety. (For evidence, just skip to two songs later on Figure 8, “Everything Reminds Me of Her.”)
4. “I Will Always Love You” by Whitney Houston
Dolly Parton wrote and recorded this song in 1973 as a rueful envoi for her mentor and champion, Porter Wagoner, and later reprised it in the 1982 movie musical The Best Little Whorehouse in Texas. Although both of those versions hit the top of the country charts, the song reached its cultural apotheosis in Whitney Houston’s epic 1991 version from the soundtrack to The Bodyguard; at the time, it was the best-selling American single in history. In Houston’s soulful account, the song moves from a quiet, a cappella intro to a blast of gospel-inflected nobility and suffering—and then drifts upward into quiet again at the very end, as though ascending to a state of grace.
5. “You’ve Lost That Lovin’ Feelin’” by the Righteous Brothers
Love crashes into a wall—specifically, producer Phil Spector’s trademark “Wall of Sound”—in this blue-eyed-soul lament, the 20th century’s most-played song on radio and TV. Cowritten by Spector and Brill Building hit makers Barry Mann and Cynthia Weil, the song begins with a sharp observation (“You never close your eyes anymore when I kiss your lips”) that leads to the chorus’s pained conclusion. But the song’s slowness and length—in 1964, 3:45 was an eternity for radio pop—give it an aching tenderness that makes its final exhortation to “bring back that lovin’ feelin’ ” sound like it has some hope of success.
6. “Back to Black” by Amy Winehouse
The late singer-songwriter crooned plenty about addiction, depression and heartbreak, but nowhere more brutally than in this moody torch song, which gave its title to her 2007 album. Winehouse penned this hit single about her falling back into bad habits after her very public break with husband Blake Fielder-Civil. The gloomy repetition of the word black during the bridge is the sound of a spiral into darkness—albeit a funky one.
7. “The Tracks of My Tears” by Smokey Robinson and the Miracles
Ah, the tears of a clown. Smokey might, indeed, “be the life of the party,” but “deep inside [he’s] blue,” people. As with the best soulful weepers, “Tracks” beautifully and economically articulates the pain of missing the one that got away. This summer-of-’65 staple—a cocktail of Smokey’s golden voice, swirling strings and horns, and a sing-along-worthy chorus—rings just as true today.
8. “Tangled Up in Blue” by Bob Dylan
Jakob Dylan once said that listening to his father’s 1975 album, Blood on the Tracks, was like listening to his parents fighting. You can hear why on its opening track, “Tangled Up in Blue”—a song that feels lived-in, true and intimate, and at the same time assumes an Odyssean quality. Inspired by Dylan’s split from his wife Sara, the song finds our narrator caught between throw-in-the-towel resignation and deep, soul-shuddering longing: tangled up in blue.
9. “Ex-Factor” by Lauryn Hill
“Doo Wop (That Thing)” may have been the flagship single from Lauryn Hill’s post-Fugees solo debut—1998’s multi-Grammy-winning The Miseducation of Lauryn Hill—but it was the languid, lovely “Ex-Factor” that rocketed the disc into the realms of extraordinary. Perfectly piquant down to the name of the song, “Ex-Factor” longs for things to be different while knowing they can’t be, ringing with frustration (“I keep letting you back in”) but humming with a love that refuses to fade.
Photograph: Nathan Johnson
10. “It’s Too Late” by Carole King
Carole King’s era-shaping 1971 album, Tapestry, was in some sense a declaration of independence from Gerry Goffin, her former husband and songwriting collaborator. The album’s first single, “It’s Too Late,” treats the end of a once-cherished relationship with bittersweet maturity, strength and striking lack of recrimination: “Still I’m glad for what we had / And how I once loved you.” It’s a song about being realistic about the end—a sentiment made all the more moving by its initial pairing, as a single, with the tremblingly erotic “I Feel the Earth Move.”
11. “Maps” by Yeah Yeah Yeahs
The enduring force of the Yeah Yeah Yeahs' most classic song lies in its expression of the inexpressible: the pithy, repetitive lyrics ("Oh say, oh say, oh say... wait") capturing that tongue-tied desperation between denial and acceptance. And as if Karen O's weepy performance in the music video wasn't already affecting enough—the singer revealed that the tears were entirely genuine, motivated by her then-boyfriend (for whom she wrote the song) showing up to the shoot.
12. “Pain In My Heart” by Otis Redding
Over and again, whether hopeful or heartbreaking, Otis Redding’s exquisite love songs bring us to our knees, like this title track off the soul icon’s 1964 debut album for Stax Records subdivision Volt (which also includes the imploring “These Arms of Mine”). If you’re really in the mood to wallow, mourn the fact that Redding perished in a plane crash at age 26, just three days after recording “Dock of the Bay.”
13. “I Will Survive” by Gloria Gaynor
Is there any song that combines female empowerment and discofied schmaltz with the same efficacy as Gloria Gaynor’s “I Will Survive”? With lyrics like “I’ve got all my life to live / I’ve got all my love to give / And I’ll survive, I will survive”—not to mention a soaring melody accented by horns and strings galore—probably not. In fact, we think the Grammy-winning hit, released in late 1978, is one of the best “screw you, loser—I’m over you” tunes of all time.
14. “Don’t Leave Me This Way” by Harold Melvin & the Blue Notes
Yes, there are other versions. Thelma Houston and the Communards both famously took this Gamble & Huff–written Philly disco cavalcade to the top of the charts. But nothing compares to the way Teddy Pendergrass’s rich and thunderous rasp emotes loss and completely connects the brain to the body.
15. “How Can You Mend a Broken Heart” by Al Green
Look, just because you’ve had your heart broken, it doesn’t mean that your mojo has to wilt away and die too—and the Reverend Al is here to spell that out via his definitive 1972 version of the Bee Gees cut. He aches just like you, but his hope hasn’t died (“Please help me mend my broken heart / And let me live again”)—and Al’s signature slow, sensual soul arrangements prove that it’s not just his heart that’s stirring.
16. “Hey, That's No Way to Say Goodbye” by Leonard Cohen
Troubadour Cohen has many a song in his arsenal to reduce grown adults to pathetic wistfulness, but this 1967 beauty is the most effective of them all. Its setup is simple—two lovers remember the happy times even as they part, via Cohen’s sweet, sad lyrics: “You know my love goes with you as your love stays with me / It’s just the way it changes, like the shoreline and the sea.” What makes it a classic, however, is how upbeat Cohen’s picked guitar, mouth harp and evocative similes feel against the reality of the situation, deftly demonstrating that losing someone can be painful but cathartic.
17. “Irreplaceable” by Beyoncé
The Destiny’s Child songbook is a bible for the woman looking to keep her man on his toes. Just in case “Bills, Bills, Bills,” “Say My Name” and “Survivor” didn’t send a clear enough message, Beyoncé reiterated her “Don’t get too comfortable” party line on this, the ultimate kick-you-to-the-curb anthem. The singer doesn’t sound the slightest bit perturbed as she shoos a disappointing lover out of her crib, advising him that he’ll find his worldly possessions “in a box to the left.”
18. “Always on My Mind” by Willie Nelson
It’s been a hit for other artists—notably Elvis Presley and the Pet Shop Boys—but “Always on My Mind” has never packed more wallop than in Willie Nelson’s recording, the title track of his eponymous 1982 album. Humble and sincere, Nelson’s plea for forgiveness exudes the quiet wisdom of genuine contrition: Having finally opened his eyes, he allows himself to hope that they can still make contact.
19. “I Don't Want to Get Over You” by the Magnetic Fields
The premise behind Stephen Merritt's magnum opus concept album 69 Love Songs is pretty explicit (hint: it's 69 love songs), but a twist hides within: He's stated the love songs are really about love songs. The obtuse statement makes sense alongside the meta-awareness this song demonstrates in quips like "I could dress in black and read Camus / Smoke clove cigarettes and drink vermouth"—it's not just a breakup narrative, but an exposé on what types of narratives we write ourselves into. So hopefully that heady conceptual business will keep your mind occupied while you try to forget about that ex.
20. “Go Your Own Way” by Fleetwood Mac
From one of rock’s most painful breakups came one of rock’s greatest breakup songs. The fallout from Lindsey Buckingham’s split with Stevie Nicks in 1976 may have made the recording of Rumours a living hell for its creators, but who cares? It spawned one of the most defiant and furious songs of a generation. No pain, no gain.
21. “Crying” by Roy Orbison
Roy Orbison’s 1961 ballad is sensitive almost to a fault: the confession of a total bawler, reduced to tears even by touching the hand of the woman who broke his heart. But the emotion soaked into Orbison’s rich, quavering voice is offset by the singer’s disciplined, deadpan cool. Even when baring his sobbing soul, he somehow seems unflappable.
22. “Don't Speak” by No Doubt
This one from 1996’s Tragic Kingdom, which Gwen Stefani penned in response to her breakup with bandmate Tony Kanal, became the band’s most successful international single—and a rallying cry for lovelorn souls the world over to go right ahead and bury their head in the sand.
23. “Back, Baby” by Jessica Pratt
"Sometimes I pray for the rain," sighs Jessica Pratt at the onset of this delicate folk tune about failed love. The song served as the lead single for the singer-songwriter's celebrated sophomore effort, 2015's On Your Own Love Again. Listening to Pratt's airy voice on this timeless, ethereal ode, we can't help but yearn for cloudy skies, too.
24. “I Just Don’t Know What to Do With Myself” by the White Stripes
Though this song was originally sung by Tommy Hunt in 1962 (and has since been covered by myriad musicians, including Dusty Springfield, Dionne Warwick, Isaac Hayes and Elvis Costello), no one has been able to capture the desperation—and frustration—behind the lyrics quite like Jack White. Recorded for the 2003 White Stripes release Elephant, this rock & roll version is perfect for the transition from heartbroken to pissed off.
Always pushing his liver and vocal cords to the limit, Nilsson injected histrionics and heart into the songs he covered as if it were HGH. His take on Randy Newman’s “Living Without You” is downbeat perfect. A year later, this Badfinger tune amped up the woe-is-me. Fact: It is impossible to listen to this Kleenex-consuming epic without balling your hands into fists and mock-karaokeing along. Next song on the album? “Coconut.” Drink the pain away.
26. “River” by Joni Mitchell
A broken heart isn't just for those who've been broken up with—as "River" attests. It's a breakup anthem that sounds as crisp and sad-in-the-bones today as it did when it was released as part of Joni Mitchell's perfectly titled Blue album in 1971. "I'm so hard to handle, I'm selfish and I'm sad, now I've gone and lost the best baby that I ever had," sings Mitchell, then later: "I made my baby say goodbye." The song is thought to have been written about Mitchell's decision to end her relationship with Graham Nash—who in turn released his astonishingly tender Songs for Beginners album. Both records are generous gifts for anyone nursing a wounded heart.
27. “I Heard It Through the Grapevine” by Marvin Gaye
You know even before the drumbeat kicks in that something is gonna go down in this song. And for anyone who’s had to hear the cheatin’, lyin’ news from someone else, this 1968 Motown single hits home. It’s become an acclaimed, Grammy Hall of Fame soul classic, covered by a range of musicians including Creedence Clearwater Revival (which made an 11-minute version for its 1970 album Cosmo’s Factory) and claymation group the California Raisins. (Grapevine, raisins—see what they did there?)
28. “Since U Been Gone” by Kelly Clarkson
You may hate American Idol. You may hate pop. You may hate it when people use u instead of you. But here’s the deal: You may also really hate your ex. And this song (off of Clarkson’s 2004 album, Breakaway) is so goddamned catchy, you can’t not belt out the chorus every time—with feeling.
29. “Roses” by Outkast
This admonishing ode to Caroline appeared on Andre 3000's half of Outkast's 2003 double album, Speakerboxxx/The Love Below. It quickly achieved anthem status, thanks in no small part to Andre's unapologetically frank lyrics. Let's be honest, sometimes cuties get away with bad behavior, but there are limits, and when your love interest crosses them, "Roses" is the perfect way to tell them to bugger off.
30. “Teardrops” by Womack & Womack
A classic in the genre of Songs to Cry to in Clubs, this 1988 electrodisco anthem tells the tale of a cheating heart haunted by its infidelity. “Footsteps on the dance floor / Remind me, baby of you / Teardrops in my eyes / Next time, I’ll be true.” This silky cut comes from Cecil (brother of Bobby) Womack and his wife, Linda—a formidable musical partnership throughout the ’80s and ’90s. This is their biggest and best hit, however, and responsible for plenty tear-stained dancing shoes over the years.
31. “Hide and Seek” by Imogen Heap
Prog-popstress Imogen Heap toes the line between poignantly lachrymose and sickeningly maudlin—so it's unsurprising her most heartachey song was immortalized in the climactic scene to a season of The O.C.. From there, the indie tune took a viral turn, rocketing from an SNL Andy Samberg sketch straight into the top charts by-way of a Jason Derulo sample. That is to say: if these forlorn folktronica vocal harmonies are sad enough for the cast of The O.C., SNL, and Jason Derulo, they're sad enough to soundtrack your boring breakup.
32. “Blame Game” by Kanye West
Mark this down: November 2010. The last time Kanye demonstrated vulnerability on a record. With an Aphex Twin sample, West balanced anger, pain and smartassery like no other MC can. It’s touching. That is, if you plug your ears before Chris Rock comes in for the coda, exclaiming, “This is some Cirque du Soleil pussy now!” By the next album, Yeezus would be a married man, grudge-rapping about fisting and ejaculating on fine fur coats.
Photograph: LASALLE College of the Arts
33. “September Gurls” by Big Star
In the encapsulation of fall-semester romance, Alex Chilton plays tough: “I loved you, well, never mind.” Never mind, he shrugs. Right. By the next line he’s confessing, “I’ve been crying all the time.” Ah, being a teenager. Listening to Big Star, it’s impossible to forget.
34. “Walk On By” by Dionne Warwick
The 1960s songwriting team of Burt Bacharach and Hal David found their perfect interpreter in Dionne Warwick, whose breezy style made the duo’s character-driven, rhythmically challenging tunes sound deceptively simple. In 1964’s “Walk on By,” one of her first Bacharach-David hits, Warwick teases out the smooth dignity in a song about the pain of rejection.
35. “Un-Break My Heart” by Toni Braxton
Queen of ’90s R&B heartache, Toni Braxton delivered more than just another sad love song when “Un-Break My Heart” hit the airwaves in 1996. A mélange of Spanish guitars and Braxton’s sultry contralto vocals, the Grammy-winning single builds a quiet storm with a dramatic crescendo as Braxton pleads with her ex to rewind their doomed relationship back to happier times. If the song’s video is any indication, those happier times included playing Twister and sharing a shower with hunky model Tyson Beckford. So, yeah, we feel ya, Toni.
36. “Marvins Room” by Drake
Who hasn't been faced off of rosé, drunk dialing the one that got away? In the lead single from 2011's Take Care, the Toronto hip-hip lord lays bare his romantic struggles over a stripped-down, wafting beat. At the time, it cemented Drake's status as the reigning king of emo rap.
Photograph: Mediacorp/Global Citizen
37. “Wrecking Ball” by Miley Cyrus
When the edgy Terry Richardson–directed video for Miley Cyrus’s power ballad was released last year, 400 million YouTubers dropped their jaws at the sight of a naked Cyrus straddling a massive steel ball. All snickers and parody videos aside, the track stands on its own as essential listening for dumpers and dumpees who have gone full-tilt into relationships and wound up emotionally demolished. And the racy video antics? Well, as BFF Lesley told us long ago, she’s just being Miley.
38. “Switch” by TLC
The penultimate track on TLC's lauded sophomore effort finds the R&B high priestesses telling possessive lovers to shove off over a groovy flip of Jean Knight's "Mr. Big Stuff." The album, CrazySexyCool, went diamond, making TLC the first girl group in history to be awarded theat status and rocketing Tionne "T-Boz" Watkins, Lisa "Left Eye" Lopes and Rozonda "Chilli" Thomas into superstardom. Any time your paramour has you feeling a little claustrophobic, just remember Left Eye's mantra: Erase, replace, embrace, new face.
39. “Skinny Love” by Bon Iver
Yeah yeah, we all know the backstory: Consummately bearded man in flannel sequesters himself to the forest to nurse a broken heart . But even if the mythology behind For Emma Forever Ago is old-hat at this point, the album's mournful, barebones folk can still tug at a heartstring and break it in two. This first single, in particular, poignantly encapsulates that painful emotional space of a relationship running on empty— perfect for those final moments before you and your partner cut the cord.
40. “Landlocked Blues” by Bright Eyes
Considering Conor Oberst makes a career out of sad-boy self-pitying omphaloskepsis, this tune from his iconic magnum mope-us, I'm Wide Awake, It's Morning, presents a surprisingly mature post-breakup perspective: "If you love something, give it away." The indie folkster somehow manages to wield the most generic of platitudes effectively without veering into farce. And anyways, when it comes to the painfully generic experience of breaking up, clichés can be more comfortingly apropos than anything else.
41. “The Scientist” by Coldplay
So potent are the breakup songs on Coldplay’s second album, 2002’s A Rush of Blood to the Head, that it may as well come with an advisory sticker for the recently split up: These songs will make you wallow in heartbreak like it’s a warm, sad bubble bath. Which may be exactly what you need. “Nobody said it was easy,” croons Chris Martin. “No one ever said it would be so hard.” And then, after the song’s sucker-punch pause: “Oh, take me back to the start.”
42. “Together” by Ruff Sqwad feat. Wiley
What does a grime break-up song sound like? Pair OG grime pioneers Ruff Sqwad with the legendary Eskiboy and you've got yourself a break-up banger. Rapping over Ruff Sqwad's original "Together" (which samples the very familiar guitar rift from the Police's "Message in a Bottle"), Wiley teases repeatedly with the rhetorical question, "(When we gonna) be together?" He fills in his verses with strong punches at his ex-lover, providing the harsh reality of things and quickly becoming his own hype man as he promises to only do better for himself. Listen to Wiley: Don't wallow in self-pity.
43. “Cry Me a River” by Julie London
This devastating torch song was written for Ella Fitzgerald in 1953, but Julie London managed to release it before the Queen of Jazz was able to get a version out. It became London’s signature song: Backed by a late-night thrum of guitar and bass that teeters ambiguously between the minor and major keys, her hushed vocals waver between tender, haughty and devastated. And then there’s that classy “too plebeian”/“through with me and” rhyme. They don’t write ’em like this any more.
44. “thank u, next” by Ariana Grande
Following your breakup with a hit single thanking each and every one of your past flames for the lessons learned from those relationships? The phrase "above it" hardly seems sufficient. Ariana teaches us all what it means to go out with grace on this suprise-release earworm.
45. “I Want You Back” by the Jackson 5
What the hell does an 11 year old know about loss? With a tip of his giant purple pimp hat, Michael sang this Motown peak with a mile-wide smile on Ed Sullivan in ’69. Still, the kid sold it like nobody else, over chords that rise and fall like a roller coaster. And nothing hurts like first love.
46. “Torn” by Natalie Imbruglia
Lurking behind the glossy sheen and shimmering guitars of this 1997 global pop hit is the age-old story of a relationship gone sour. “Torn” was originally recorded by American alt rockers Ednaswap, but saucy Aussie Natalie Imbruglia’s rendition perfectly encapsulates the unhappy transition from honeymoon optimism to the realization that “Illusion never changed / Into something real.” Seriously, we totally hate it when that happens.
47. “Dry Your Eyes” by the Streets
Men’s emotions can sometimes be harder to read than a pureed copy of Proust. In 2004, however, the Streets’ Mike Skinner just laid it right on the line. While Skinner’s verses found him crestfallen at having been chucked, it’s the choruses that made the tune so beloved, delivering man-to-man comfort and kindly reassurances that there are “plenty more fish in the sea.”
48. “Believe” by Cher
If you don’t think this is a brilliant song, then it’s probably only because you’ve heard it way too many times. Cher’s (temporary) resurrection as a dance-pop diva in 1998 has raised plenty of hackles over the years—not least for its then-unprecedented use of Auto-Tune—but at its heart it’s simply a great breakup song in the air-punchingly empowered tradition of “I Will Survive”: “I’ve had time to think it through / And maybe I’m too good for you.” When we’re going through a rough time, we could all use a bit of that attitude.
Foto: Cortesía Blur
49. “No Distance Left to Run” by Blur
From the bleak opening line—“It’s over, you don’t need to tell me”—to Damon Albarn’s final cries, this song is like a punch to the gut. Written, allegedly, about Albarn’s split with Elastica frontwoman Justine Frischmann, the tune perfectly encapsulates the weariness and resignation all too often experienced during a breakup, in that period between acceptance and finally moving on. Sigh.
Foto: Vertigo Records
50. “Say Hello, Wave Goodbye” by Soft Cell
“Take your hands off me!” cries Marc Almond on this 1982 synth-pop tearjerker. “I don’t belong to you, you see.” The follow-up to Soft Cell’s hit single “Tainted Love,” “Say Hello” perfectly encapsulates the ambivalence and denial at love’s end. Almond reflects that the pair must’ve been “the standing joke of the year,” adding later, “I never knew you / You never knew me.” And of course, were any of this true, you wouldn’t be crying now, would you?
Expect to sniff along to the all-time classics, get down like you’re at a wedding disco to dance-party titans like Madonna, and feel a smile spread across your face when you hit the number one spot and think of your own number one sweetie.