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What makes a song a "breakdown song"? Does it accept to be empowering, à la "I Will Survive" or nearly of the songs on Lemonade? Should it be for the lonely, like Carole Male monarch'south "It'south Too Tardily" or Bob Dylan's "If Yous See Her, Say Hullo"? Does it have to address the breakdown in the lyrics? (Taylor Swift has many entrants in this category, and Marvin Gaye penned an entire album about his divorce.) What about songs with a famous backstory, like "Cry Me a River" or any track off of Rumours?

We hither at The Ringer believe that since heartache comes in many forms, so should the breakdown song. And in laurels of Valentine'southward Solar day, we decided to dig deep into the genre. Below, you'll notice our ranking of the 50 greatest breakup songs of all time, as voted on by our staff. The listing spans several decades and many unlike moods, but all are rooted in some type of pain. There was merely one rule for the final ranking: just ane song per artist was included to avoid Dolly Parton or even Drake from dominating.

So if you're lone, fire up our playlist and cry forth as yous read our thoughts on each aspirant. If y'all're happily fastened, you lot tin can still dive in—these are some of the greatest songs ever recorded, and that'south true whether yous're in your feelings or not. Maybe you'll gain a greater appreciation for your current human relationship. After all, breakup songs resonate only when you know what it's like to lose in love. —Justin Sayles

50. "We Are Never E'er Getting Dorsum Together," Taylor Swift

Most heartbreaking line: "You would hide away and find your peace of mind / With some indie record that's then much cooler than mine"

I of the most savage breakup songs in history, "We Are Never Always Getting Back Together" encapsulates the severe "fuck that guy!" energy that follows a long-overdue parting of means. We've all had that post-fight bluster with our friends: "Ugh … and so he calls me up and he'south like, 'I nevertheless love yous,' and I'm like … 'I just … I mean this is exhausting, you know, like, we are never getting back together. Like, always.'" Flippant, triumphant, and entirely wearied past All Men, Taylor Swift gave us the perfect soundtrack for breakdown recovery. — Kate Halliwell

49. "I Miss You lot," Blink-182

Most heartbreaking line: "I need somebody and ever / This sick strange darkness / Comes creeping on and so haunting every time"

"I Miss You" is like a minimalist/emo have on Meat Loaf. It rules. The ii best things about this number are Travis Barker's uncomplicated only persistent drumbeat and Tom DeLonge's entrance on the second verse. It's part of the 1000 pop punk tradition of showing you mean business by going up an octave, of which "I Miss You lot" (along with the Starting Line's "The Best of Me") is the exemplar.

Don't just take my discussion for information technology, though. Consider Grammy-winning producer Finneas's have: "Tom comes into that song similar he was on a balcony and he jumped off the balustrade onto the vocal." —Michael Baumann

48. "It'due south Too Late," Carole Male monarch

Nigh heartbreaking line: "Only we just can't stay together, don't you feel information technology, besides? / Nevertheless I'thousand glad for what nosotros had and how I once loved y'all"

"It'due south Too Late" is a crushing ode to the about mutual kind of breakup. The natural procedure of 2 people growing autonomously is equally heartbreaking equally it is commonplace, and King sings in a tone perfectly situated between her sorrow and the shrugging access that "we really did effort to get in." Her conversational delivery early in the song brings the states into the living room, diner, or sidewalk where "the talk" betwixt her and her about-to-exist-ex is happening: "One of us is changing, or possibly we just stopped trying," she sings, patently laying out the central, blameless reasons for why most people end up separating. The song is defined by its maturity and its conciliatory attitude, only equally with actual breakup conversations, that doesn't make it any easier to hear. —Cory McConnell

47. "Un-Interruption My Eye," Toni Braxton

Nigh heartbreaking line: "I tin can't forget the twenty-four hours y'all left / Fourth dimension is so unkind"

This is a perfect example of the kind of breakup song you hear on the radio (or, in the late '90s, mayhap the guild—the Frankie Knuckles house remix yet goes) and, on a normal mean solar day, only hear another pop song, simply when yous're experiencing heartache, what originally sounded like songwriting clichés become the truest words you've ever heard. "I have cried a lot of nights," you lot think, getting out of bed for the first time in days to catch a roll of toilet paper since you ran out of Kleenex. "Life is brutal without you here beside me," you murmur, staring into the bleak chasm of loneliness you now know as life. "I would literally exercise anything on God'south green globe to hear you lot say you beloved me once again," you realize with the greatest clarity you lot've always experienced. Anyway, where are my altos at? This is our karaoke song. — Kjerstin Johnson

46. "Mr. Brightside," the Killers

Nigh heartbreaking line: "Now they're going to bed and my stomach is sick / And it'southward all in my head"

Maybe it's not exactly right to call "Mr. Brightside" a breakdown song; peradventure information technology's more than accurate to call it a right-earlier-the-breakup song, an I-imagined-my-girlfriend-was-cheating-on-me-so-intensely-that-she-actually-started-adulterous-on-me song. But that's all really clunky, and so let's take being slightly wrong for the sake of cleanliness. Either way, "Mr. Brightside" is an iconic mid-aughts song that's perfect for yell-karaoking and that pulls off the difficult trick of just repeating one poesy over and over. Also, Eric Roberts in the video. —Andrew Gruttadaro

45. "She'due south Gone," Hall & Oates

Almost heartbreaking line: "Get up in the morn, wait in the mirror / 1 less toothbrush hanging in the stand"

The dynamic duo of Daryl Hall and John Oates became plumage-haired, MTV-borne superstars in the '80s, just their rise to greatness begins here, with the breakout hit from their second album, 1973's oddly/heartbreakingly named Abased Luncheonette. "She's Gone" is luscious and silky and deceptively light, all Motown grandeur by fashion of blue-eyed Philly soul, but that lightness only underscores the exquisite heaviness of murmured verse lines like "Get up in the forenoon, await in the mirror / Worn as the toothbrush hanging in the stand." (Or probably information technology'south "One less toothbrush," which of grade is fifty-fifty heavier.) The chorus, past contrast, is gigantic and majestic and crushing, punctuated past cloudbursting lamentations of "She's gone! / Oh why? / Oh why?" The boys only got bigger from here, merely they certainly never got sadder. —Rob Harvilla

44. "Tyrone," Erykah Badu

Most heartbreaking line: "I merely desire it to be, you lot and me, like it used to be, baby / But ya don't know how to act"

The second-all-time moment on this viciously sultry ho-hum jam, the crown jewel of Erykah Badu's 1997 album Alive, is the stupendous opening line: "I'm gettin' tired of your shit / You don't always purchase me nothin'." The first-all-time moment is all the women in the crowd immediately shrieking with please and, ane fears, recognition. "Tyrone" is named for one of an unnamed deadbeat lover's numerous deadbeat friends: "Every fourth dimension we go somewhere," Badu purrs with lethal authorisation, "I gotta achieve down in my bag / To pay your style and your homeboy'south way and sometimes your cousin's way." It is the gender-flipped riposte to Friday's "Farewell, Felicia," and in fact turned up as a joke in 2000's Adjacent Friday; information technology "followed me thru my career like an obsessed 10 fellow," as Badu put it on Instagram in 2017, while shouting out her backup singers, whose sardonic and sublime "Call him!" chant is the third-best moment. —Harvilla

43. "Love Is a Battlefield," Pat Benatar

Most heartbreaking line: "Do I stand in your way / Or am I the best affair you've had?"

The agonizingly propulsive signature hit from flamethrower-voiced '80s popular queen Pat Benatar laments not so much a breakup as a near-breakup in progress, an acknowledgement that truthful love means almost breaking up pretty much all the fourth dimension: "Believe me / Believe me / I can't tell you why / But I'grand trapped past your beloved / And I'm chained to your side." It's a karaoke classic you lot have no business attempting, a cheeseball Reagan-era blast of eternal profundity, and a striking annunciation that sometimes the only thing worse than splitting upwards is non splitting up: "Do I stand up in your way / Or am I the best thing you've had?" she wails with 18-carat desperation, and the answer, of course, is both. —Harvilla

42. "Devil in a New Dress," Kanye West

Almost heartbreaking line: "Throwing shit effectually, the whole place screwed up / Maybe I should call Mase and so that he could pray for us"

Nosotros're not fifty-fifty talking most the whole song—we're talking near 20 or so seconds of Bink product subsequently Kanye'south second poetry, just before Rick Ross'southward simply poesy, arguably one of the best in his career. In information technology, he describes West's near-fatal car crash in 2002 every bit an aborted climb "up the Lord's ladder," and honestly, that'southward exactly what the collection of power strings sound similar on this bridge. A climb up the Lord'southward ladder, a departure from Earth, a ane-manner trip to anywhere but here. —Micah Peters

41. "Suspicious Minds," Elvis Presley

Most heartbreaking line: "We tin't go along together / With suspicious minds / And we can't build our dreams / On suspicious minds"

You can meet the ripples of "Suspicious Minds" throughout the course of breakup song history, from "Railroad train in Vain" to "Dancing on My Ain," which, you know, information technology'south Elvis. Merely beyond the juxtaposition of its relatively upbeat music and depressing-as-hell lyrics, I love the construction of this song, with a peppy guitar intro and verses that build into a chorus that goes from G major to very, very Eastward minor and merely doesn't e'er actually resolve. This might not be the only reason the vocal fades out but there's no existent suitable catastrophe betoken for the last notes of the chorus, and then it always drops back into a verse or a bridge or some other chorus. "John Jacob Jingleheimer Schmidt" resolves more easily. Just like a cleaved relationship. —Baumann

xl. "The Tracks of My Tears," Smokey Robinson & the Miracles

Almost heartbreaking lines: "Although she may exist cute, she'south just a substitute / Because you're the permanent i"

On this classic Motown tearjerker, Smokey embodies the thought of the distressing clown improve than any song ever has. He'south the life of the political party—using jokes similar a clown uses makeup—just inside, he's wounded, pining for a past lover. He's dating someone new, but he's not thinking of her. (Side annotation: I don't know who I'm sadder for here, Smokey or the rebound he's walking around town with.) He may accept wiped away the tears, but they've left their mark. And the makeup only makes the tear tracks that much more apparent. —Justin Sayles

39. "Tears Dry on Their Own," Amy Winehouse

Most heartbreaking line: "Then this is inevitable withdrawal / Even if I finish wanting you / And perspective pushes through / I'll be some adjacent man'due south other adult female soon"

On "Tears Dry on Their Own," Amy Winehouse demanded that Amy Winehouse accept her ain advice. "I cannot play myself over again, I should simply be my ain all-time friend," she warns. "Non fuck myself in the head with stupid men." These lines that pried the vocal open were one of Winehouse's hallmarks as a writer—"Tears" begins in the dumps, in the aftermath. Simply during every emotional uncoupling comes the point where you gaze into the mirror, stick your finger in your reflection'southward breast, and tell them to terminate being such a dumb, whiny baby. —Peters

38. "Needed Me," Rihanna

Virtually heartbreaking lines: "Fuck your white horse and a wagon / Bet you never could imagine / Never told y'all yous could have information technology / You needed me"

This vocal is so piffling and I dear it. Rihanna basically made a striking off the "Sike, you lot thought!" meme and DJ Mustard added an unforgettable beat behind information technology. This is one of those bangers that you lot and your girls boom post-breakdown, pre-going-out. So, after you all sing in unison: "Don't get it twisted / Y'all was only some other nigga on the hit list / Tryna gear up your inner issues with a bad bowwow," y'all all burst into laughter thinking about the human who is now barely a retentiveness. Rihanna'due south confidence and savageness is really on an untouchable level. (Call back, this song is on the same album where she sings "sex with me is so amazing" over and over.) Long may she reign. —Jordan Ligons

37. "So Sick," Ne-Yo

Nearly heartbreaking line: "Gotta change my answering machine, now that I'yard solitary / 'Crusade right now it says that we can't come to the telephone"

The earworm of a generation! Ne-Yo said no to sappy ballads in more ways than 1 with "So Ill," giving us an R&B nail hitting for everyone sick of regular, schmegular dearest songs. Set to the world'due south catchiest trounce, Ne-Yo mourns a past relationship and all the solar day-to-day changes that come with moving on. "Gotta change my answering machine, now that I'm alone / 'Crusade right now it says that we can't come to the telephone … Gotta fix that agenda I have that'south marked July 15 / Considering since there'southward no more you, at that place's no more than anniversary." Fifteen years later, we withal can't turn off the radio. —Halliwell

36. "Nosotros Vest Together," Mariah Carey

Near heartbreaking line: "When you lot left I lost a role of me / Information technology'southward still and so difficult to believe / Come back baby, please / 'Cause we belong together"

*Sighs.* This is easily the most played-out, lamentable breakdown song of the early on 2000s. Everyone idea about someone who could've/should've been their soul mate when this dropped in 2005. But at present if it comes on the radio and y'all're either happily single or in a solid relationship, your eyes volition glaze over, guaranteed. When the first two seconds of the infamous shell come through my speakers, I'm already changing the station. Information technology'due south simply then abrasive, and then Mariah.

Yous may call up that you won't find someone else to lean on when times get rough or someone to talk to you lot on the telephone until the lord's day comes up, but allow me tell you lot, yous will and yous'll be fine. Breakups suck, but please don't torture your broken centre (or your ears) by listening to this song on echo. —Ligons

35. "If Y'all Run across Her, Say Hello," Bob Dylan

Most heartbreaking line: "Say for me that I'm all right, though things get kind of ho-hum / She might remember that I've forgotten her, don't tell her it isn't so"

The inspiration for Bob Dylan's masterful Blood on the Tracks has e'er been debated. Critics have long causeless that the anthology is virtually Dylan's separation from his wife, Sara. The couple'due south son, Jakob, reportedly believes that Blood is about his parents. Merely Dylan himself has steadily denied that his masterpiece is autobiographical, even maxim instead that it's based on … Chekhov's short stories. "I don't write confessional songs," Dylan told Cameron Crowe during the release of the immersive (and, in the context of this quote, ironically named) Biograph. The truth is, it doesn't matter. Claret strikes such a chord considering the heartache information technology mines feels at in one case securely personal and universal.

That'southward most palpable on "If Y'all See Her, Say How-do-you-do," which brings us into a fractured relationship in a way that'south both effortlessly relatable ("We had a falling out, like lovers often will") and hyper-specific ("And to think of how she left that nighttime, it even so brings me a chill"). Information technology'due south not Dylan'south flashiest or heaviest or best song, but it is my favorite, a gentle, intimate portrait of lost love and lasting ache. Like so much of his best work, it's propelled past its verse, the raw insights virtually how it feels to exist alive. The song cycles through the same phases that so many of u.s. do while processing heartbreak: denial, despair, anger, desire. It floats on a current of remorse ("Sundown, yellow moon, I replay the by / I know every scene by center, they all went by so fast") all the same manages to convey the kind of longing that leads, cautiously, back toward hope ("If she's passing dorsum this way, I'm non that difficult to find / Tell her she tin can look me up, if she'south got the time"). After plenty listens, and enough heartache of your own, you realize that "If You Meet Her, Say Hello" isn't really a breakup song. It's a love alphabetic character. — Mallory Rubin

34. "Don't Look Back in Anger," Haven

About heartbreaking line: "Stand up up beside the fireplace / Take that wait from off your face / 'Crusade you ain't ever gonna burn my eye out"

The closest I've ever come to living in an episode of Glee was when my high school French class spontaneously broke out singing "Don't Look Dorsum in Anger." I don't recall why, just it cemented this song (at least for me) every bit a ballad of communal weltschmerz, rather than personal sadness or regret, like a fin-de-siècle "Yous'll Never Walk Alone." (For instance: "Don't Look Back in Anger" became a kind of unofficial anthem after the Manchester bombing in 2017.) Haven knows a affair or two well-nigh writing for the communal sing-along, the importance of the languid, memorable tune and the propulsive chord modify—this vocal would bear about the same emotional weight if it were but a championship and a chorus. —Baumann

33. "Every Breath You Take," the Police

About heartbreaking line: "Since y'all've gone I've been lost without a trace / I dream at night, I can only meet your face"

This spectacularly maudlin New Wave ballad, which anchored the Police force's 1983 goliath Synchronicity and reigned every bit ane of the biggest radio hits of the decade, is creepy as all hell, very much by blueprint: an unrepentant stalker manifesto that doesn't and so much describe spurned love in terms of surveillance as it describes full state surveillance in terms of spurned love: "Every movement you make / Every vow you break / Every smile you faux / Every claim you stake." And and so on. "I'll be watching you," Sting concludes a couple dozen times throughout, but it's the chest-pounding bridge where the trio's creepy-soulful frontman does some of his best belting, his all-time pleading, his best super-creepy emoting and enunciating: "I feel then common cold and I long for your em-brace." Fun fact: He started writing the song at Ian Fleming's writing desk on the James Bond author's luxe Jamaican manor, which might not be creepy, but it's certainly weird. —Harvilla

32. "Don't Speak," No Dubiousness

Most heartbreaking line: "As nosotros die, both you and I / With my head in my easily, I sit and weep"

I mean, honestly, information technology takes a lot of guts to drop a Spanish classical guitar solo in the middle of an angsty '90s alt-stone song. Information technology also takes a lot of guts to write a vocal nigh breaking upward with the bass player in your ring and then make a music video for the song that has shots in it like the ane beneath: Don't speak, literally.

No Doubt's first striking is a work of art, full of raw, youthful emotion and complex arrangements. It'due south beautiful, brutal, painful, and incendiary, all at once. —Gruttadaro

31. "Thinkin Bout You," Frank Ocean

Almost heartbreaking lines: "Practice yous not think so far ahead? / 'Cause I been thinkin' tour forever"

Sometimes y'all have to lie to yourself to go through heartache. They weren't good enough for me. I tin do meliorate. I didn't beloved them, I only thought they were cute. Frank Sea's "Thinkin Tour You" exposes that kind of posturing for what it is: a facade. No, I wasn't crying well-nigh you, and past the way, I also own waterfront property in Idaho. Frank's conspicuously still hung upwards on the past even if his old flame isn't. And the but way to work through the pain is to drop the lying and come up clean with himself. Information technology's tender, it's sweet, but most of all, it's honest. —Sayles

30. "I'chiliad Goin' Downwards," Mary J. Blige

Most heartbreaking lines: "Why'd you accept to say goodbye? / Look what you've done to me / I can't end these tears from fallin' from my eyes"

No matter your electric current relationship status, yous will for sure sing your heart out when this song comes on. I do non intendance, I am Mary J. when the chorus hits. By the cease of the song—a embrace of Rose Royce's 1976 unmarried—you've "gone down" so much that you're on the floor, eyes closed, hoop earrings in, and belting, "My whole world's up-[dramatic pause]-side down!" I can't exist the just one, right?

Also, remember when Tamera sang this song for the talent evidence on Sister, Sis? Iconic. —Ligons

29. "Cypher Compares 2 U," Sinéad O'Connor

Most heartbreaking lines: "I could put my artillery around every boy I see / Only they'd only remind me of you"

Breakups are freeing; breakups are imprisoning. When you come up out of a yearslong human relationship, you accept to relearn how to live without that person in your life. Parts of that procedure are beautiful—reconnecting with quondam friends, picking up a new hobby, shaking off the shackles. But the breakdown sticks with you. You run into your ex'southward best friend at the bar, or you hear a song that you lot both loved. Sometimes, it's a minor annoyance. Other times, it's an globe-shattering event. Yous're relearning how to alive, but living is difficult.

I tin't call up of a song that ameliorate captures that duality than "Nada Compares 2 U," the 1990 O'Connor hit originally penned by Prince in 1985. You tin exercise whatever you lot want: You can political party all night, you tin can consume at a fancy restaurant, you can put your artillery around all the boys and girls y'all'd like, just it doesn't matter. Information technology's not them, and cypher will exist. Your best promise is just giving in and living for yourself. —Sayles

28. "Marvin'south Room," Drake

Near heartbreaking line: "The woman that I would try / Is happy with a skilful guy"

Drake is at his best when he'due south subversive considering he masks the gaslighting with a softer sadness. "The woman that I would try / Is happy with a good guy," he sings. Is he happy for her? The lines propose that there's at least a chance. Drake pauses, and so goes full Drizzy Deleterious: "But I've been drinkin' so much / That I'ma phone call her anyway." He gain to tell her that the homo she's with isn't good enough to replace what they had. Information technology's the archetype overstep from an ex, but the longer he goes on, nosotros realize it's more nigh his pride and alien emotions about his life choices than it is about her. Drake spirals, telling her he's "had sex four times this week / I can explain," that he'southward sponsoring women, that he can't terminate partying and asking for naked pictures. Exactly what your ex-girlfriend wants to hear, I'm sure. At to the lowest degree there'due south a voicemail interlude. —Haley O'Shaughnessy

27. "Just a Friend," Biz Markie

Most heartbreaking line: "Oh, snap! Guess what I saw? / A fella tongue-kissin' my girl in her oral cavity"

Turns out this woman did not have what Biz Markie needed. Equally he singsplains, he became kitten smitten with a woman at one of his shows. Y'all'd think that this would have happened to him all the time, just information technology did not. This was "the get-go girl I ever talked to," Biz told EW concluding yr. "Every time I would call out to California, a dude would pick upwards and hand her the telephone. I'd exist similar, 'Yo, what'southward upwards [with him]?' She'd say, 'Oh, he'southward only a friend. He's nobody.'" Not taking the hint, Biz flew out to California to surprise her a week earlier than planned. When he showed upward, at that place was a guy "tongue-kissing my girl in her mouth."

Biz. My guy. Sit downward. Let's talk. Starting time off, she was not your daughter. You met her one time. Second, you did not catch her tongue-kissing a dude. You stalked her. Third, it was extremely obvious that this friend was non just her friend. What Biz Markie needed was someone to listen to his story and give him honest feedback about his predicament. You know, a friend. —Danny Heifetz

26. "Burn," Usher

Most heartbreaking line: "But y'all know, gotta let it become / 'Cause the party ain't jumpin' like information technology used to / Even though this might bruise you lot / Let it burn"

I couldn't imagine someone breaking up with me with the lyrics to this song. Usher is all over the place. He says he loves me, but our relationship has to come to an end; he says he'south pain and he'south not happy, only he'southward breaking downward and crying. Deep down he knows information technology's best, but he hates the thought of me being with someone else. Go your shit together, Usher!

Yet, for all of its confusing dorsum-and-forth, this is a breakup classic. It preaches the ideology of forcing yourself to allow go even when you don't know what you're going to practise without your boo. After a heartbreak, anybody has found themselves teetering on the line betwixt regret and freedom. Conductor's "Burn" allows y'all to tap into that while simultaneously yelling out, "Information technology'south been fifty-eleven days, umpteen hours, and Imma exist burnin' till y'all return!" —Ligons

25. "Piece of My Heart," Big Brother & the Holding Company

Most heartbreaking line: "But each time I tell myself that I, well I can't stand the pain / But when you hold me in your arms, I'll sing it in one case once again"

If yous're always at your wits' end, tragically obsessed with someone who treats y'all like shit, you can find some catharsis in the controlled anarchy of Janis Joplin'southward vocal performance on "Piece of My Heart." Go ahead and scream along. You lot won't sound equally skilful as Janis, only yous'll certainly experience a hell of a lot better afterward.

Once your anger fades a picayune, yous tin switch over to the original recording of this song, released a year earlier in 1967 and sung by Erma Franklin (yes, that's Aretha's older sis). Or if you demand some more twang accompanying your despair, you can attempt the Religion Hill version. I likewise won't judge you if the only person who can ease your hurting is Shaggy (or Beverley Knight, Melissa Etheridge, Steven Tyler, Kelly Clarkson, or one of countless other artists).

Written by Jerry Ragovoy and Bert Berns, "Slice of My Middle" is one of the most relatable and enduring songs virtually Some Fuckboi in the history of fuckbois. The call-and-response construction of the chorus builds those simmering resentments and releases them with a precipitous, primal cry. Undoubtedly, at that place will exist new versions of this vocal until the finish of time⁠—because it's an accented banger—but likewise considering … men. —Matt James

24. "Skinny Honey," Bon Iver

Most heartbreaking line: "And I told you to be patient / And I told yous to exist fine"

A skillful dominion for breakup songs is that at that place has to be a function that you can yell along to, unencumbered by giddy things like constraint and self-sensation. The chorus of Bon Iver's "Skinny Love" has a peachy one, especially for anyone who's but exited a relationship and feels compelled to heap all the blame on the other political party.

You know the story by now: In 2006, Justin Vernon broke up with his girlfriend, packed up his car, and collection into the Wisconsin wilderness, emerging only later on recording an album of weepy breakup songs. That origin tale has been repeated so frequently that it's get soft mush, obscuring the real truth: That For Emma, Forever Ago—and particularly "Skinny Dearest"—are profoundly reflective, intelligent, moving documents well-nigh the breakdown of a relationship. —Gruttadaro

23. "Hold Up," Beyoncé

Almost heartbreaking line: "Can't you see in that location'south no other man above you lot? / What a wicked manner to treat the daughter that loves you"

It'southward hard to express real injure over an uptempo beat and brand the heartbreak convincing. Yet Beyoncé is believable in "Concur Up," a painful bookkeeping of the emotions that come after discovering that your partner has cheated. Lemonade was inspired by truthful events—i.e., it'southward Beyoncé coming to terms with Jay-Z being unfaithful. Infidelity brings on a very specific type of devastation: You lot're mad; you're miserable; you're humiliated. You switch from one emotion to another in a matter of minutes. She opens the vocal with confidence: No other woman can give what she can. "Concord up, they don't love you similar I beloved y'all." In a breath, she'due south less sure of herself: "What's worse, looking jealous or crazy?" Beyoncé settles on crazy, then returns to anger. "You lot permit this good love become to waste." —O'Shaughnessy

22. "Cry Me a River," Justin Timberlake

Near breaking lyric: "You lot didn't know all the means I loved y'all, no / So you lot took a chance / And made other plans"

Entering 2002, Justin Timberlake wasn't regarded as much more a teeny bopper. His group 'NSync was one of the defining groups of the boy band era, and he was its charismatic face. (The beautiful i, if you will.) He even had the perfect girlfriend for that type of stardom: Britney Spears, with whom he pulled off this iconic denim fit. So the couple broke up, JT dissever from 'NSync, and "Cry Me a River" happened.

In his commencement solo megahit, Justin insinuates his love has cheated on him ("You lot don't have to say what you did / I already know, I found out from him") and writes her off for good. He's already cried about it, and now it's her plough. But no amount of her tears tin can undo the harm; he'south gone. You didn't have to do much sleuthing to effigy out he was singing about Britney. That celebrity intrigue, Timbaland'due south sharp production, and an instantly memorable music video combined to make "Weep Me a River" the most iconic breakup song of the early 2000s, catapulting him to some other level of stardom. He had divide with not only Britney, but also his past, and he was ready for the earth. —Sayles

21. "With or Without Y'all," U2

Nigh heartbreaking line: "She got me with nothing to win / And zip left to lose"

Nil changes if nothing changes, every bit they say, and "With or Without Y'all" exists in that hopelessly recursive "I hate that I dear you" space. This song was U2's first no. 1 hitting in the U.South., even though, Bono has said, "it's a very odd-sounding vocal … it kind of whispers its way into the world." But information technology's not the whispers that resonate virtually, nonetheless, information technology's all those wails, similar the crescendo of Bono'southward aching, eminently singalong-able ahhh-ahhh-ahh-ahhhhhs, or the painful, everlasting notes from the Edge's "space guitar," engineered to hold a tone equally if information technology were a grudge. "Psychotic restraint" is how Bono characterized the Edge's spare work on this runway, a description that could double as breakup communication. —Katie Baker

xx. "Jolene," Dolly Parton

Most heartbreaking line: "And I can easily understand / How yous could easily take my man / Simply yous don't know what he means to me, Jolene"

While other female person country singers might've handled their man's newfound fascination with a beautiful redhead by, say, digging a key into the side of his pretty trivial souped-upwardly 4-bicycle drive, or—just spitballing here—threatening to send her to Fist City, Parton simply pleads for mercy. The desperate pitch of her appeal, set against a frantic Dorian-mode guitar riff, sets the stakes far higher than those you might find in more often than not stern country songs about cheatin', lyin', and being untrue. Whatever armchair scholar of Parton's work can tell you she cloaks feminist manifestos within marketable diddies most everyday experiences. I've always taken the song's urgency to imply something that every woman learns eventually: Relationships tin be both romantically fulfilling, and, too often, an economic lifeboat to a improve life. In "Jolene," our narrator isn't merely grasping onto her man, she's grasping for survival. —Alyssa Bereznak

19. "I Heard Information technology Through the Grapevine," Marvin Gaye

Most heartbreaking line: "Do you lot program to let me get / For the other guy you loved before?"

This song was first released by Gladys Knight and the Pips in 1967. A yr later on Marvin Gaye released a slower version of it on his album In the Groove. Perhaps the song resonated with Gaye because he married a 41-year-former woman when he was only 24, and their marriage was total of infidelities. "I was in love with the idea of dearest," Gaye one time said. Or at to the lowest degree that's what I heard through the grapevine. —Heifetz

eighteen. "Ex-Gene," Lauryn Loma

Almost heartbreaking line: "Where were you when I needed you?"

"Ex-Factor" is more a breakup song, it's near recognizing a toxic relationship before you accept the words to call it a toxic relationship. Each line, so honest it hurts, is about the fruitless search for reason in a scenario devoid of it. Hill's lyrics capture the worst of the worst of a relationship on the rocks: the hurting, the complicity, and the unwillingness to give up on a love you call up is withal at that place, cached beneath the bullshit.

When information technology hitting airwaves again in 2018 on Drake'due south pandering notwithstanding irresistible "Overnice for What," it was virtually similar recognizing and reclaiming a past self—one who might take cried along to the original. Now, equally wiser, more than Empowered™ listeners, we heard the remixed, catchy hook devoid of its devastating verses and bopped our heads as Drake reminded us of how brusque life is. Still, no one can capture the raw, uncomfortable emotion that Lauryn originally did—and no one ever will. —Johnson

17. "You're So Vain," Carly Simon

Most heartbreaking line: "Well, yous said that we fabricated such a pretty pair / And that y'all would never leave / Only yous gave away the things you loved / And one of them was me"

Far earlier Taylor Swift sent her fans on subtweet scavenger hunts, Carly Simon penned a epic kissoff that, cheers to its cocky-referential chorus, left the world wondering whom it was nearly and what they could've possibly washed to acrimony her. More twoscore years of speculation afterward, nosotros now know that the vocaliser was describing the role player Warren Beatty. (She added in a recent, withering interview that, although the song describes three divide men, Beatty "thinks the whole matter is about him.") We may never know what company he kept (cough: Mick Jagger?), but the lasting power of Simon's articulate-eyed takedown stands equally a referendum on the unchecked male ego, whether its contained in the torso of a dashing role player or a moody fuckboy. —Bereznak

16. "Dancing on My Own," Robyn

Most heartbreaking line: "Yeah, I know information technology's stupid, I just gotta encounter information technology for myself"

Final year, following a Robyn evidence at Madison Square Garden, elated concertgoers continued the party on the A/C/E train subway platform, breaking into a silly public performance of "Dancing on My Own." You wouldn't typically look a breakup song to be the one that leads New Yorkers to such displays of commonage joy, but nigh breakdown songs aren't like this i: a song you can strut to, a club anthem, a scene-stealer, a story of lonesomeness that yet finds its solace in a oversupply. It's a song nigh moving on—I just came to say goodbye—but as well about, just, moving. The vocaliser might be alone in the corner, and she might know information technology's stupid, only she's out there dancing, at least. —Bakery

fifteen. "Thank U, Next," Ariana Grande

Most heartbreaking line: "Wish I could say, 'Cheers' to Malcolm / 'Cause he was an angel"

This vocal is a conclusion to exist done with suffering over a relationship, to recommit to oneself, to focus on healing and establishing new patterns. To not merely rehearse past losses just to envision future victories, and besides to alive in the moment, to exist hither now.

This to exercise the bodily, day-in, day-out work of being happy. —Peters

14. "End of the Route," Boyz Ii Men

Near heartbreaking line: "Information technology's unnatural"

Both the joyous genesis and abject expiry knell for billions of '90s junior-high-gymnasium-dance relationships that only lasted the length of the song itself, "Terminate of the Route," which rose to power on 1992'due south Boomerang soundtrack, is one of the biggest hits in pop-music history. Like, "13 straight weeks atop the Hot 100" large. Like, "The 'Quondam Town Route' of Its Day" big, a tearjerking shout-along anthem for lovelorn belters too devastated to even accept their horses and get out the house. The concluding a capella chorus is a signature moment in American cultural history, at once exhilarating and devastating: "It's unnatural / Y'all vest to me / I vest to y'all." The word unnatural has never sounded so natural, and so miserable. —Harvilla

xiii. "Dreams," Fleetwood Mac

Nearly heartbreaking line: "Now hither you go again, y'all say yous want your freedom / Well, who am I to continue yous downwardly?"

Even xl-plus years on, to hear Stevie Nicks softly moaning, "What you lot had ... and what you lost / And what you had ... and what you lost" to the guy playing guitar is to live forever, and to imagine that guitar actor dropping dead from remorse on the spot. (Lindsey Buckingham, of class, has been known to chugalug out a sweetly caustic breakdown anthem or 2 himself.) Equally the second (and best!) runway on 1977'south zillions-selling Rumours, "Dreams" is both radically overexposed and nonetheless somehow criminally underrated, fixed to its iconic identify, time, and circumstances but also shockingly timeless. (Zoë Kravitz rhapsodizes it in the pilot of Hulu's new High Fidelity remake series to prove her stone-nerd bona fides.) Pair information technology with "Silver Springs" for maximum effect. —Harvilla

12. "How Can You Mend a Cleaved Heart," Al Green

Most heartbreaking line: "Permit me live once again"

There'south heartbreak, then in that location'due south Al Dark-green heartbreak. (Not to slight the original Bee Gees version—Green is all I know when I'm going through it.) He's exasperated from the get-go, wondering whether he'll e'er recover from the love that went away. The agony is plenty to contemplate nature itself in the chorus: "How can you mend a broken heart? / How can y'all finish the rain from falling down? / How tin you stop the dominicus from shining? / What makes the world get round?" Green is begging for answers, for "somebody, please" to come up ready him. He pleads, "Let me live again." Life as he knew it is over without this person, and equally long equally the vocal is on, it feels over for united states, too. —O'Shaughnessy

11. "Torn," Natalie Imbruglia

Most heartbreaking line: "I'1000 all out of faith / This is how I experience, I'm cold and I am shamed / Lying naked on the floor"

There's a bad breakdown, at that place's rock bottom, and then at that place'south being "cold and shamed, lying naked on the floor." Natalie Imbruglia'south 1997 one-hit wonder (and sneaky cover) doesn't mince words in describing exactly how shitty it feels to put your faith in the wrong homo. (Or any human being, depending on how hard you vibe with this song.) "Torn" has taken a turn for the over-covered and over-memed these days, only you're lying if y'all say y'all don't notwithstanding hitting that chorus every fourth dimension. —Halliwell

10. "I Volition Survive," Gloria Gaynor

Most heartbreaking line: "And so you felt like dropping in and simply expect me to be free / Well at present I'm saving all my lovin' for someone who's lovin' me"

This 1978 disco colossus is then singular, then monolithic, so wedding-dancefloor-ingrained that it inappreciably scans equally a breakup song at all: As ecstatic and empowering fuck-y'all anthems get, it is the glamorous grandmother to Lizzo's "Truth Hurts" and Ariana Grande's "Thank U, Adjacent" and Beyoncé's "Irreplaceable" and roughly fifty,000 other cocky-affirming pop hits. What truly elevates New Jersey diva Gloria Gaynor's all-timer, though, is its sociopolitical import: "I Will Survive" has long been a stirring battle hymn for the LGBTQ community, for survivors of domestic violence, for anyone who can relate in any way, frivolously or otherwise, to the bluntly iconic line "I'm saving all my lovin' for someone who's lovin' me," which of course is everybody. She knows y'all're afraid; she knows yous're petrified. But she also knows you lot won't stay that manner for long. —Harvilla

nine. "Ain't No Sunshine," Neb Withers

Most heartbreaking line: "Wonder this time where she's gone / Wonder if she's gone to stay"

To make a song from 1971 about a video game from 2010: Dante'south Inferno is an RPG based loosely on the first anthem of the Divine Comedy. I say loosely because EA Dante has rippling muscles and a massive scythe, his only protections against the legions of the night, who've stolen his honey Beatrice. I never played it, but a friend who did described his frustration with the game: It'south as if its conclusion got farther abroad the more fourth dimension he devoted to information technology. A Super Bowl commercial showed Dante sprinting toward Hell's gaping mouth determined only, yous know, definitely doomed. As he descends you hear the low croak of Pecker Withers'southward voice, pining afterward a lost lover: "Ain't no sunshine when she's gone, only darkness everyday." My last breakup didn't involve a giant flaming devil monster, but it did feel like a similarly hopeless uphill battle. —Peters

8. "Someone Like You," Adele

About heartbreaking line: "Sometimes it lasts in love, merely sometimes it hurts instead"

The queen of heartbreak has never been better than on sophomore album 21, and 21 doesn't go much better than "Someone Similar You." Adele'due south ode to the 1 who got away is maybe the most universally adored tearjerker of the past decade; starting with that elementary piano line and catastrophe in that burdensome hook: "Sometimes it lasts in love, but sometimes it hurts instead." And of class, that voice! Watching the elementary black and white music video now, it's striking how babe-faced Adele was at 21, despite her delivery of a vocal that displays and then much emotional maturity. She wishes the best for her ex ("Old friend, why are you and then shy?"), but damn, she's still hurting. Aren't we all! —Halliwell

7. "I Desire You Back," The Jackson v

Most heartbreaking lyrics: "Someone picked you from the bunch, i glance was all it took / Now it'southward much too late for me to take a second look"

Perchance the most outwardly joyous song in this unabridged ranking, "I Want You Back" spins a tale that anyone who's always taken someone for granted volition understand. An 11-year-old Michael Jackson is at his nigh precocious hither, singing almost the girl whom he didn't fully appreciate until someone else stole her heart. Now he just wants another chance to prove that he knows how to care for her right. Michael, of grade, didn't write the vocal—it was penned by Berry Gordy and Co.—but he sells it in a fashion that someone two or three times his historic period never could. A leopard can't change its spots, but if it sounds this good trying to convince you it can, why non give it ane more chance? —Sayles

6. "Since U Been Gone," Kelly Clarkson

Most heartbreaking line: "How come I'd never hear you say / 'I just wanna be with y'all' (be with you) / I judge you lot never felt that way"

There is a moment in every breakup where, after a few weeks of self-pity, you shed your sweatpant cocoon, stride outside, and, with the instantaneity of a prophylactic band snap, suddenly know deep within your heart that your ex was an insufferable blowhard. Kelly Clarkson'due south mosh-adjacent power pop carol embodies the newfound cocky-balls that comes with that realization. Information technology too happens to be enshrined in a pop culture moment that I will forever acquaintance with being a melodramatic 16-twelvemonth-one-time millennial: "Since U Been Gone" was written by pop lords Max Martin and Dr. Luke, who ripped its entire musical construction from the far more poetic Yep Yeah Yeahs striking, "Maps," and so—after being passed upwards past both Pinkish and Hilary Duff—was sung by the very outset winner of the then-fledgling reality Television bear witness American Idol. The AIM-friendly "U" in the title is just the icing on the block. —Bereznak

5. "Ms. Jackson," Outkast

Nigh heartbreaking lyric: "Forever never seems that long until you're grown / And notice that the day-by-twenty-four hours ruler can't be besides incorrect"

Sometimes breaking up with your significant other'south family is merely as hard as breaking up with them. Big Boi and André 3000 understood that on "Ms. Jackson," a song dedicated to Kolleen Maria Wright, the mother of Erykah Badu, with whom André had a child. Three Stacks's poesy is especially poignant—his intentions were good, simply things took a turn for the worse. It'south a harsh reality: Most relationships are born with an expiration date, no matter how bright the flame burned at the showtime. As far as apology songs go, it's pretty nuanced and sincere. And Wright seems to have bought it: Erykah said in 2016 that her mother even has a "MSJACKSON" license plate. —Sayles

4. "I Will Always Love Yous," Whitney Houston

Nearly heartbreaking line: "Please don't weep / We both know I'm not what you, you need"

Dolly Parton wrote i of the most dynamic love songs ever with "I Will Always Love Yous." Whitney Houston, who sang a embrace for the film The Bodyguard, made a worldwide hit with her astounding range. Both versions are wonderful for different reasons, though Parton'due south honeyed, wobbly original is best for heartbreak. For one, it's authentic: She wrote the song for her former manager and professional partner, Porter Wagoner, after she decided to get out him. Parton is sympathetic, yet determined to become. Equally she sings in the bridge, it'southward bittersweet. They are both better off this way, she argues, only wishes him nothing just "joy and happiness." Ane of the hardest relationship lessons is that two people can dearest each other and information technology still not be right for either—thanks to Dolly and Whitney, information technology was one learned early. —O'Shaughnessy

three. "I Tin't Make You lot Dear Me," Bonnie Raitt

Almost heartbreaking line: "I'll close my eyes / So I won't see / The honey you don't feel when you're property me"

You lot might be a girlfriend, a hubby, a partner, or even a friend with benefits. Whatsoever office you play in service of love, information technology comes with a label that sets expectations. There is clarity and comfort in knowing where you stand up with someone. But despite all of our semantics and promises, the terrifying reality of our love lives is that love itself can be a ruthlessly nonbinding agreement, an at-will arrangement. Fifty-fifty more frightening is that it's ofttimes our hearts—not us—calling the shots.

What sets "I Can't Make You Honey Me" apart from almost breakup songs is that information technology takes identify at the most painful point of a breakup: acceptance. It'due south not a post-breakup anthem of empowerment or a drastic plea to stay together. Information technology'southward the total strength of the disorienting one-two dial of loss and loneliness. It'south the world-shattering moment when you lot surrender the fight.

Bonnie Raitt's arresting functioning of this song (written by Mike Reid and Allen Shamblin) carries the weight of a lifetime in and out of love. She sets downward her slide guitar, sits Bruce Hornsby down at the piano, and sings the absolute fuck out of this song with confidence and grace. The vocal used on the Luck of the Draw album recording was Bonnie's start accept. "I Tin't Brand You Beloved Me" has been covered by endless artists, included on several Greatest Songs Of All Fourth dimension lists, and inducted into the Grammy Hall of Fame.

The songs that touch on us most deeply are the ones that unite us through the most human of shared experiences. Eventually, nosotros all acquire that you can't brand someone'south heart feel "something it won't." But should you one twenty-four hour period find yourself at rock bottom, suddenly lonely in darkness—whether it's your outset time or your 14th—you lot can feel a little bit less solitary knowing that Bonnie'due south been there, as well. —James

2. "You Oughta Know," Alanis Morissette

Nigh heartbreaking line: "Does she know how you told me you'd agree me until you lot died, till you died / But you're yet live"

Alanis Morrisette was 19 years old when she recorded that ballad of bitterness "You Oughta Know" in one accept at 11 p.m. "All those vocals are but her at the end of the dark," said her cowriter Glen Ballard in an oral history of the album Jagged Footling Pill, "singing something she just wrote." The result was a revelation in its ragged emotion, all fingernail scratches and fellatio, a piece of work of art centering the seething spirals of rage. (That it was possibly inspired by Uncle Joey remains both iconic and deeply weird, merely also makes sick sense: You oasis't truly been jilted until you lot've been jilted by someone who'south non even that cool, you lot know?) "Yous Oughta Know" totally scandalized my mom every time it came on the radio in the '90s, and what's more, it features both Flea on bass and Dave Navarro on the guitar. What more than could you want—other than sweet, sugariness vengeance? —Baker

i. "Royal Rain," Prince

Virtually heartbreaking line: "I never meant to cause you any sorrow / I never meant to crusade yous whatever pain"

Purple rain, according to an unsourced quote that'south widely attributed to Prince Rogers Nelson, is the result of blood mixing with the sky, which is a sort of apocalyptic drama that only Prince could conjure. But you don't even need to sympathize what imperial rain is to feel "Royal Rain," a power ballad to end all power ballads.

Some breakup songs are hateful, some are mournful, others are empowering. Only "Purple Rain" has the power to experience like everything all at once, a near-religious feel of a vocal that has the ability to heal like no other. In times of trouble, put "Purple Pelting" on, and let him guide you. —Gruttadaro

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Source: https://www.theringer.com/music/2020/2/14/21137264/50-greatest-breakup-songs-ever-ranking

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