The 50 Best Breakup Songs

Commiserate or celebrate being newly single with these break up songs from classic tear-jerkers to epic kiss-offs.

We all know that the best breakup songs—unlike the best love songs, which usually provide a pleasant uplift—can be irritating, painful and downright depressing. You just got dumped after all! Or maybe you did the dumping. Either way, let’s face it—you’re both probably better off. They were no good for you! Cue up one of these kiss-off songs, shed a tear if you must and say goodbye. These tunes will have you spinning something from our list of best party songs in no time.

“Love Will Tear Us Apart” by Joy Division

The lead singer of seminal Manchester, U.K., band Joy Division, Ian Curtis was one of indie rock’s greatest losses—a troubled genius who let his shyness fall away onstage, but lived his personal life in quiet agony. “Love Will Tear Us Apart” is Curtis at his most melancholic, and the ultimate chronicle of a relationship’s breakdown. The lyrics are ostensibly about Curtis and his wife, Deborah, but they also refer to the inner rifts that contributed to his fragile psychological state and his eventual suicide in May 1980—a mere five months after this track was recorded. For listeners, though, its eternal chorus—“But love, love will tear us apart again”—says everything there is to say about the mixed pleasure and pain of being in thrall to another human being. It is, without a doubt, the best breakup song ever created: Not just a ditty about dwindling affections, but a searingly precise evocation of human fragility. We are simple beings, it seems to say, made and broken by small moments, and powerless against the tide of our own emotions.—Jonny Ensall
Most heartbreaking lyric: “And we’re changing our ways / Taking different roads”

“You Oughta Know” by Alanis Morissette

Purported subject of this song Dave “Uncle Joey” Coulier insists that his breakup with Alanis was amicable. But there’s nothing well-wishing about this most vengeful of jilted-lover odes, the object of many a cathartic karaoke jam since its release in 1995. Like all great rages, Alanis lets hers build: The tune begins like an unexploded bomb, and you can almost smell the cordite in the air as she murmurs: “I want you to know / I’m happy for you…” And then the guitar kicks in, and the uncomfortable questions begin: “Is she perverted like me? / Would she go down on you in a theater?” By the time she’s growling about scratching her nails down someone else’s back and hoping you feel it, it’s already too late, Coulier. This one’s for the most demonstrative of your five stages—white-hot anger.—Jenna Scherer
Most heartbreaking lyric: “'Cause the love that you gave that we made wasn't able/ To make it enough for you to be open wide”

“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 the Parc de Saint-Cloud (a historic park just outside of Paris), was cited by Miley Cyrus as the inspiration for her 2013 “Wrecking Ball” video. Whatever your opinion of that spectacle, it can’t be denied that more than two decades later, O’Connor’s wrenching rendition still packs a punch.—Kristen Zwicker
Most heartbreaking lyric: “Like a bird without a song / Nothing can stop these lonely tears from falling”

“What Becomes of the Brokenhearted” by Jimmy Ruffin

What becomes of the brokenhearted? They end up listening to this solid-gold soul classic, over and over again, is what. The sad and newly-single can find solace in its driving, determined verses; tantalizing string refrain; major-to-minor key changes; and knowledge that yes, we’ve all been through it, and survived. Recorded in 1966 for Motown, the song is among the label’s most-covered hits. Anyone who’s turned to music for comfort (that’ll be all of us, then) will understand why.—Sophie Harris
Most heartbreaking lyric: “I’ll be searching everywhere just to find someone to care”

“Hey, That's No Way to Say Goodbye” by Leonard Cohen

Tear-jerking Canadian 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.—Jonny Ensall
Most heartbreaking lyric: “But now it’s come to distances and both of us must try.”

“Don't Think Twice, It's Alright” by Bob Dylan

The man born "Robert Zimmerman" lifted the melody to this wistful folk classic from a traditional country diddy, but inserted his own lyrics—a fortunate change considering the original, "Who's Gonna Buy Your Chickens When I'm Gone?," holds a few too many chicken-related lines to land the same emotional punch. The tune feels weary, lived-in and intimate, with our narrator leaving behind simmering resentment for quiet resignation. It's not so much an optimistic end as a stoic acceptance that "it is what it is"—and what more can you really ask for post-breakup?—Rohan Samarth
Most heartbreaking lyric: “Goodbye is too good a word, babe / so I just say fare thee well”

“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.—Oliver Keens
Most heartbreaking lyric: “Baby I'd give you my world / How can I, when you won't take it from me”

“Someone Like You” by Adele

You’d have to be some kind of monster not to mist up a bit at Adele’s 2011 tear tugger. A Saturday Night Live sketch has been written about its irresistible emotional pull; even dogs, it seems, are not immune. Part of what gives the song this power, paradoxically, is its rejection of sadness. The heartbroken singer enacts a performance of brave stoicism (she’s fine, she’ll move on, she’ll find someone else), but we know that she is fooling herself (she’s a mess, she’s still stuck, the best someone else is still the guy she has lost). But her willful refusal to cry about it lets us do the sobbing for her.—Adam Feldman
Most heartbreaking lyric: “I had hoped you'd see my face and that you'd be reminded / That for me it isn't over”

“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.—Adam Feldman
Most heartbreaking lyric: “It makes me just feel like crying, ‘cause baby, something beautiful's dyin'”

“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.—Adam Feldman
Most heartbreaking lyric: “We both know I’m not what you need.”

“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.—Bruce Tantum
Most heartbreaking lyric: “I used to cry / but now I hold my head up high!”

“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.—Jenna Scherer
Most heartbreaking lyric: “Life is like a pipe / And I'm a tiny penny rolling up the walls inside”

“Untrue” by Burial

"Untrue" is the title track from Burial's second full-length album—a beautiful 13-track work throughout which the enigmatic electronic musician mixes elements of dubstep, UK garage, hardcore and distorted vocal samples. His method of sampling is so clever that the resulting samples hardly sound like their original versions. In this track, Burial samples Beyoncé's "Resentment" ("To the way I feel inside / And it's all because you lied"), Ernie Halter's "Whisper" ("We could be friends / Away from my heart") and Sarah McLachlan's "Angel" ("And the endlessness that you fear"). Burial creates an over-6 minute ballad about hurt, anger and betrayal by isolating just these lyrics, repeating them like a repeated stabbing of the heart. Genius.—Vivienne van Vliet
Most heartbreaking lyric: “The way I feel inside / it’s all because you lied”

“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 III. Recorded for the 2003 White Stripes release Elephant, this rock & roll version is perfect for the transition from heartbroken to pissed off. Bonus: Sofia Coppola directed a lingerie-clad, pole dancing Kate Moss in the music video, which should at least help get your blood pumping again.—Kate Wertheimer
Most heartbreaking lyric: “Like a summer rose needs the sun and rain / I need your sweet love to beat love away”

“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?).—Kate Wertheimer
Most heartbreaking lyric: “I know a man ain't supposed to cry / But these tears I can't hold inside”

“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.—Kate Wertheimer
Most heartbreaking lyric: “How can a loser ever win?”

“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.”—Sophie Harris
Most heartbreaking lyric: “Science and progress do not speak as loud as my heart”

“I Don't Want to Get Over You” by the Magnetic Fields

“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.—Rohan Samarth
Most heartbreaking lyric: “I guess I should take Prozac, right? / And smile all night at somebody new”

“Against All Odds (Take a Look At Me Now)” by Phil Collins

When you’re dumped, you’re allowed to indulge in melodrama. It is acceptable to sit around in a robe for days and take big bites of the pillow synthesizers, ice-cream crooning and cookie-dough drums comprising this most powerful and ballad-y of power ballads. A leftover from his solo debut that was recorded years later, in 1984, for a Jeff Bridges cheese-noir flick, “Against All Odds” gave the former Genesis man his first No. 1 hit in America.—Brent DiCrescenzo
Most heartbreaking lyric: “There's just an empty space / And there's nothing left here to remind me, just the memory of your face”

“Flesh Without Blood” by Grimes

Throwing away hours of painstaking work like Claire Boucher did when she scrapped an entire album of Visions followup material?—that's kind of a breakup in and of itself. The artistic overhaul set the stage for this first actual single from Art Angels, a celebratory relationship goodbye which mines sugary pop instrumentation to tell a former lover, "I don't care anymore."—Rohan Samarth
Most heartbreaking lyric: “It's nice that you say you like me / But only conditionally”

“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 San Francisco 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.—Kristen Zwicker
Most heartbreaking lyric: “Play it in reverse then you'd find / That you'd better reconsider all the love you took and then cast aside.”

“Heartbreak Hotel” by Elvis Presley

Think your breakup is sad? This song’s lyrics were inspired by a 1956 newspaper article about a man who jumped to his death from a hotel window, leaving a note with the single line “I walk a lonely street.” But suicides don’t sell records, so Presley crooned instead about a place where the bellhop’s tears flow, the desk clerk dresses in black and brokenhearted lovers can cry away their gloom. (And potentially hook up? Was this place also a brothel? No? Opportunity lost.)—Kate Wertheimer
Most heartbreaking lyric: “If your baby leaves you and you have a sad tale to tell / Just take a walk down Lonely Street to Heartbreak Hotel”

“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.”—Adam Feldman
Most heartbreaking lyric: “Now you look so unhappy, and I feel like a fool”

“Single” by Everything But The Girl

This track appears on British duo Everything But The Girl's ninth studio release, Walking Wounded—an album which was ahead of its time with modern elements of electronica, from house to drum and bass. "Single," produced by Ben Watt, is slow and thoughtful, as Tracey Thorn delicately—and vulnerably—sings about the post-breakup confusion when newly single. Question after question, Thorn conveys the feeling of total emptiness and loss of self after separating from a partner in life. Definitely grab a box of Kleenex for this one.—Vivienne van Vliet
Most heartbreaking lyric: “If no one calls and I don't speak all day, do I disappear?

“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.—Tim Lowery
Most heartbreaking lyric: “Outside I'm masquerading / Inside my hope is fading”

“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.—Sophie Harris
Most heartbreaking lyric: “Tell me who I have to be to get some reciprocity”

“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.” You’re tempted to shout out an “Amen,” but Queen Bey seems to be doing just fine without any reinforcement.—Hank Shteamer
Most heartbreaking lyric: “I won't lose a wink of sleep / 'Cause the truth of the matter is replacing you is so easy”

“Marvins Room” by Drake

We've all been there. 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. It's a potent song that drew much critical acclaim—and cemented Drake's status as the reigning king of emo rap.—Kristen Zwicker
Most heartbreaking lyric: “I need you right now, are you down to listen to me?”

“I Keep Forgettin’ (Every Time You’re Near)” by Michael McDonald

We don’t typically think of the breakup song as a climate hospitable to sultry funk, but somebody forgot to notify Michael McDonald. On this 1982 lite-rock staple, the former Doobie Bro laments being hung up on an ex, as a rhythm section stocked with session aces glides through a monster groove—famously sampled by Warren G on 1994’s “Regulate.” Whoever the subject of the tune was, it’s hard to imagine her not shimmying back into the husky crooner’s arms when she heard this immortal jam.—Hank Shteamer
Most heartbreaking lyric: “I keep forgettin' we're not in love anymore / I keep forgettin' things will never be the same again”

“Putting the Dog to Sleep” by the Antlers

I don't know what's worse: a terminally-fated relationship or Fido going to beagle heaven. Either way, it's a sick game of "would you rather." This closing track to The Antler's 2011 album Burst Apart actually concerns the former topic—breathe easy, Fido—and draws from fertile source to explore that morose thematic territory: classic soul records, for which frontman Peter Silberman has a noted predilection.—Rohan Samarth
Most heartbreaking lyric: “Well, prove to me / I'm not gonna die alone”

“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 OC. 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 OC, SNL, and Jason Derulo, they're sad enough to soundtrack your boring breakup.—Rohan Samarth
Most heartbreaking lyric: “Spin me around again and rub my eyes / This can't be happening”

“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.—Jonny Ensall
Most heartbreaking lyric: “Nothing that I do or feel, ever feels like I felt it with you”

“Apart” by The Cure

Sometimes, when nursing a broken heart, you need to stomp the poor thing into the pavement. For those moments when the only way up is down, there's no better vessel to ride into the depths of despair than the Cure's "Apart." The song appeared on the iconic British outfit's ninth and highest-charting album, Wish, and is a perfect storm of drifting synths, distant guitar echoes and unflinching lyrics. He waits to hear her say forgive/But she just drops her pearl-black eyes/And prays to hear him say I love you/But he tells no more lies. Go on, twist the knife.—Kristen Zwicker
Most heartbreaking lyric: “She waits all night to feel his kiss / But always wakes alone”

“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 and the 2008 genesis of "hipsterdom" ensues. 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.—Rohan Samarth
Most heartbreaking lyric: “I tell my love to wreck it all / Cut out all the ropes and let me fall”

“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.—Adam Feldman
Most heartbreaking lyric: “I love you even more than I did before, but darling what can I do / For you don't love me”

“Maps” by Yeah Yeah Yeahs

The enduring force of the Yeah Yeah Yeah's most classic single lies in its ability to tap into the inexpressible, as the pithy, repetitive lyrics ("Oh say, oh say, oh say... wait") capture that tongue-tied desperation which lives between between denial and acceptance. And as if Karen O's weepy performance in the music video wasn't already affecting enough—the alt-punk icon recently revealed that the tears were entirely genuine, motivated by her then-boyfriend Angus Andrew of Liars (for whom she wrote the song) showing up to the shoot.—Rohan Samarth
Most heartbreaking lyric: “My kind's your kind / I'll stay the same.”

“Heaven Knows I’m Miserable Now” by the Smiths

Morrissey is as endemic to the heartbroken as a pint of Ben & Jerry’s. You can’t list songs about being depressed and not include the Smiths, the wearing-your-pajamas-all-day of indie-rock bands. Well, certainly, on a shallow level the British quartet works on that level. Take this 1984 single at face value, judge it by its bleak black & white cover, and it’s a pit of despair. But the band is far too cynical for straightforward funk (er, of the mental kind). “I was looking for a job, and then I found a job, and heaven knows I’m miserable now,” Morrissey croons. That’s countered with barbs like, “Why do I smile at people I’d rather kick in the eye?” Marr matches the subtle bipolar shifts with chiming chords that roller-coaster from major to minor. Sometimes, the Smiths got depression better than big pharma.—Brent DiCrescenzo
Most heartbreaking lyric: “Why do I give valuable time to people who don't care if I live or die?”

“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.—Rohan Samarth
Most heartbreaking lyric: “I feel more like a stranger each time I come home”

“It Ain't Me Babe” by Johnny Cash and June Carter

Sometimes the hardest part of breaking up is admitting you're not right, or even good, for each other. Originally written by Bob Dylan in 1964, this sweet, sad song found its true voice with Johnny Cash and June Carter, who recorded a version together for Cash's 1965 album Orange Blossom Special. There's something about the two singing together in agreement that makes the song's realizations less sorrowful—it's always easier when it's mutual.—Kate Wertheimer
Most heartbreaking lyric: “I'm not the one you want, babe / I'll only let you down”

“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.—Adam Feldman
Most heartbreaking lyric: “Make believe that you don't see the tears / Just let me grieve in private”

“River” by Joni Mitchell

A broken heart isn't just for those who've been broken up with—as "River" attests, 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.—Sophie Harris
Most heartbreaking lyric: “I wish I had a river I could skate away on / But it don't snow here.”

“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.—Adam Feldman
Most heartbreaking lyric: “Give me one more chance to keep you satisfied”

“Roses” by Outkast

This admonishing ode to Caroline appeared on Andre 3000's half of Outkast's 2003 double album, Speakerboxxx/TheLoveBelow. 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.—Kristen Zwicker
Most heartbreaking lyric: “She needs a golden calculator to divide the time it takes to look inside”

“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?" answering multiple variations of "Never, we don't wanna be with each other." 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. Don't wallow in self-pity; listen to Wiley.—Vivienne van Vliet
Most heartbreaking lyric: “When are we gonna realise that it won't last if we both tell lies?”

“Since U Been Gone” by Kelly Clarkson

You may hate American Idol. You may hate power 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.—Kate Wertheimer
Most heartbreaking lyric: “How come I've never heard you say, I just want to be with you?”

“We Are Never Ever Getting Back Together” by Taylor Swift

Taylor Swift’s penchant for mining her own relationship drama to find songwriting gold is well documented; when the results are as catchy and downright fun as this kiss-off gem, we have no complaints. “We Are Never Ever Getting Back Together” finds the country-pop starlet and her ex (reportedly actor Jake Gyllenhaal) traipsing about in that awkward on-again, off-again state of limbo. The back and forth goes on, the ex’s transgressions pile up, but ultimately, “swift justice” wins out and we’re treated to one of the best breakup songs, like, ever.—Michael Chen
Most heartbreaking lyric: “You would hide away and find your peace of mind with some indie record that's much cooler than mine”

“Train in Vain” by the Clash

This song, tacked on to the end of 1979's London Calling, is not for wallowing. It's the song you play when you're emerging from that post-breakup anger and are ready to rock (and maybe even dance) again. It's for the moments when you feel simultaneously like the bigger person and also self-satisfied in your accusations against your former lover. It's absolutely necessary during breakups, and a pretty great tune the rest of the time as well.—Kate Wertheimer
Most heartbreaking lyric: “You don't understand my point of view / I suppose there's nothing I can do”

“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.—Kristen Zwicker
Most heartbreaking lyric: “I can't trust a relationship with no trust, and that's a fact”

“Somebody That I Used to Know” by Gotye featuring Kimbra

Wouter De Backer, a.k.a. Gotye, didn’t have a duet in mind when he first put pen to paper for “Somebody That I Used to Know,” but when he reached the end of the first verse, he knew it needed a little something more. Along came fast-rising New Zealand singer-songwriter Kimbra, whose impassioned delivery bolstered the tune with a new, fiery perspective. The result was a wildly successful crossover hit, which topped the charts in 18 countries and took home Record of the Year at the 2013 Grammys.—Kristen Zwicker
Most heartbreaking lyric: “You can get addicted to a certain kind of sadness”