U Know When You See Someone and U Hear That Heart Snap

What makes a song a "breakup song"? Does it have to be empowering, à la "I Will Survive" or about of the songs on Lemonade? Should information technology exist for the lonely, like Carole King's "It'southward Too Belatedly" or Bob Dylan's "If Yous Meet Her, Say Hello"? Does information technology accept 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, similar "Cry Me a River" or any track off of Rumours?

We here at The Ringer believe that since heartache comes in many forms, so should the breakdown song. And in honor of Valentine's Day, we decided to dig deep into the genre. Below, you lot'll detect our ranking of the fifty greatest breakdown songs of all time, every bit voted on by our staff. The list spans several decades and many different moods, but all are rooted in some type of pain. There was only one rule for the last ranking: just one song per artist was included to avoid Dolly Parton or even Drake from dominating.

So if you're solitary, burn down up our playlist and cry forth as you read our thoughts on each entrant. If you're happily fastened, you tin nevertheless dive in—these are some of the greatest songs ever recorded, and that's true whether you're in your feelings or non. Perhaps yous'll gain a greater appreciation for your current human relationship. Afterwards all, breakdown songs resonate but when you know what it's like to lose in love. —Justin Sayles

50. "We Are Never Ever Getting Dorsum Together," Taylor Swift

Most heartbreaking line: "Y'all would hide away and find your peace of heed / With some indie tape that's and so much cooler than mine"

One of the well-nigh savage breakup songs in history, "We Are Never Ever Getting Dorsum Together" encapsulates the severe "fuck that guy!" free energy that follows a long-overdue parting of ways. We've all had that post-fight rant with our friends: "Ugh … and then he calls me up and he's similar, 'I still love you,' and I'thou like … 'I but … I hateful this is exhausting, you know, like, we are never getting back together. Like, ever.'" Flippant, triumphant, and entirely exhausted by All Men, Taylor Swift gave us the perfect soundtrack for breakdown recovery. — Kate Halliwell

49. "I Miss You," Glimmer-182

Most heartbreaking line: "I need somebody and e'er / This sick strange darkness / Comes creeping on and then haunting every fourth dimension"

"I Miss You" is like a minimalist/emo have on Meat Loaf. It rules. The two best things about this number are Travis Barker'due south simple but persistent drumbeat and Tom DeLonge'southward entrance on the second poesy. It's part of the grand pop punk tradition of showing y'all hateful business by going up an octave, of which "I Miss You" (along with the Starting Line's "The All-time of Me") is the exemplar.

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

48. "It's Likewise Late," Carole King

Virtually heartbreaking line: "Only we just can't stay together, don't you feel it, also? / Nonetheless I'1000 glad for what nosotros had and how I once loved you"

"It's Too Tardily" is a crushing ode to the almost common kind of breakup. The natural procedure of ii people growing apart is every bit heartbreaking as it is commonplace, and King sings in a tone perfectly situated betwixt her sorrow and the shrugging access that "we really did try to arrive." Her conversational delivery early on in the song brings united states into the living room, diner, or sidewalk where "the talk" between her and her well-nigh-to-be-ex is happening: "I of us is changing, or maybe we just stopped trying," she sings, apparently laying out the cardinal, clean-living reasons for why virtually people end upward separating. The song is defined by its maturity and its conciliatory mental attitude, but as with actual breakup conversations, that doesn't arrive any easier to hear. —Cory McConnell

47. "United nations-Interruption My Heart," Toni Braxton

Most heartbreaking line: "I can't forget the twenty-four hours you left / Time is so unkind"

This is a perfect example of the kind of breakup song y'all hear on the radio (or, in the late '90s, possibly the club—the Frankie Knuckles house remix nevertheless goes) and, on a normal day, just hear another pop vocal, but when you're experiencing heartache, what originally sounded like songwriting clichés get the truest words you lot've e'er heard. "I accept cried a lot of nights," you think, getting out of bed for the first time in days to grab a curl of toilet paper since you lot ran out of Kleenex. "Life is cruel without you here abreast me," you murmur, staring into the dour chasm of loneliness y'all now know as life. "I would literally do anything on God's green earth to hear you say yous love me once more," you realize with the greatest clarity you've ever experienced. Anyway, where are my altos at? This is our karaoke vocal. — Kjerstin Johnson

46. "Mr. Brightside," the Killers

Most heartbreaking line: "Now they're going to bed and my breadbasket is sick / And it'southward all in my caput"

Perhaps it's not exactly right to call "Mr. Brightside" a breakup song; maybe information technology'due south more than accurate to telephone call it a right-before-the-breakdown song, an I-imagined-my-girlfriend-was-cheating-on-me-so-intensely-that-she-actually-started-cheating-on-me song. But that's all really clunky, then let'southward accept being slightly incorrect for the sake of cleanliness. Either way, "Mr. Brightside" is an iconic mid-aughts vocal that's perfect for yell-karaoking and that pulls off the difficult trick of just repeating ane verse over and over. Too, Eric Roberts in the video. —Andrew Gruttadaro

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

Well-nigh heartbreaking line: "Get upward in the morning time, look in the mirror / One less toothbrush hanging in the stand"

The dynamic duo of Daryl Hall and John Oates became plume-haired, MTV-borne superstars in the '80s, just their ascension to greatness begins here, with the breakout hit from their second album, 1973'south oddly/heartbreakingly named Abased Luncheonette. "She's Gone" is luscious and silky and deceptively light, all Motown grandeur past fashion of blue-eyed Philly soul, but that lightness but underscores the exquisite heaviness of murmured verse lines like "Go up in the morning, look in the mirror / Worn every bit the toothbrush hanging in the stand up." (Or probably it's "1 less toothbrush," which of course is even heavier.) The chorus, by contrast, is gigantic and majestic and burdensome, punctuated by 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

About heartbreaking line: "I but want it to exist, you and me, like it used to exist, baby / But ya don't know how to act"

The second-best moment on this viciously sultry deadening jam, the crown jewel of Erykah Badu's 1997 anthology Live, is the stupendous opening line: "I'grand gettin' tired of your shit / You don't ever purchase me nothin'." The commencement-best moment is all the women in the oversupply immediately shrieking with delight and, one fears, recognition. "Tyrone" is named for one of an unnamed deadbeat lover'southward numerous deadbeat friends: "Every time we go somewhere," Badu purrs with lethal authorization, "I gotta attain downwards in my purse / To pay your mode and your homeboy's style and sometimes your cousin'south way." It is the gender-flipped riposte to Friday'south "Bye, Felicia," and in fact turned upwardly as a joke in 2000's Side by side Fri; it "followed me thru my career similar an obsessed 10 young man," equally Badu put it on Instagram in 2017, while shouting out her backup singers, whose sardonic and sublime "Call him!" chant is the 3rd-best moment. —Harvilla

43. "Beloved Is a Battlefield," Pat Benatar

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

The agonizingly propulsive signature hit from flamethrower-voiced '80s pop queen Pat Benatar laments not then much a breakup as a near-breakup in progress, an acknowledgement that true dear means almost breaking up pretty much all the time: "Believe me / Believe me / I can't tell you lot why / Merely I'yard trapped past your love / And I'g chained to your side." Information technology's a karaoke classic you have no business attempting, a cheeseball Reagan-era boom of eternal profundity, and a striking declaration that sometimes the but thing worse than splitting up is not splitting upward: "Do I stand in your fashion / Or am I the best thing you lot've had?" she wails with genuine desperation, and the answer, of course, is both. —Harvilla

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

Most heartbreaking line: "Throwing shit around, the whole place screwed upwardly / Peradventure I should call Mase so that he could pray for united states of america"

We're non even talking about the whole song—we're talking nigh 20 or and so seconds of Bink production later Kanye'south 2d verse, but before Rick Ross's only verse, arguably one of the all-time in his career. In it, he describes Due west'southward near-fatal car crash in 2002 as an aborted climb "upwards the Lord'south ladder," and honestly, that's exactly what the collection of power strings sound like on this bridge. A climb upwardly the Lord's ladder, a departure from Earth, a one-style trip to anywhere but hither. —Micah Peters

41. "Suspicious Minds," Elvis Presley

Virtually heartbreaking line: "Nosotros can't go on together / With suspicious minds / And nosotros can't build our dreams / On suspicious minds"

You tin can encounter the ripples of "Suspicious Minds" throughout the form of breakup vocal history, from "Train in Vain" to "Dancing on My Own," which, you lot know, it'due south Elvis. But beyond the juxtaposition of its relatively upbeat music and depressing-every bit-hell lyrics, I love the structure of this vocal, with a peppy guitar intro and verses that build into a chorus that goes from One thousand major to very, very Due east small-scale and just doesn't ever really resolve. This might not be the only reason the song fades out only there'southward no real suitable ending betoken for the concluding notes of the chorus, so information technology ever drops dorsum into a verse or a bridge or another chorus. "John Jacob Jingleheimer Schmidt" resolves more easily. Just like a broken human relationship. —Baumann

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

Nigh heartbreaking lines: "Although she may exist cute, she'southward just a substitute / Because yous're the permanent one"

On this classic Motown tearjerker, Smokey embodies the thought of the sad clown better than whatever song ever has. He's the life of the party—using jokes like a clown uses makeup—simply within, he'southward wounded, pining for a past lover. He's dating someone new, but he'southward non thinking of her. (Side note: I don't know who I'g sadder for here, Smokey or the rebound he's walking around boondocks with.) He may have wiped away the tears, merely they've left their mark. And the makeup only makes the tear tracks that much more credible. —Justin Sayles

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

Most heartbreaking line: "So this is inevitable withdrawal / Even if I terminate wanting y'all / And perspective pushes through / I'll exist some side by side man'southward other woman soon"

On "Tears Dry on Their Own," Amy Winehouse demanded that Amy Winehouse take her ain advice. "I cannot play myself again, I should just be my own best friend," she warns. "Not fuck myself in the head with stupid men." These lines that pried the vocal open were i of Winehouse's hallmarks as a writer—"Tears" begins in the dumps, in the aftermath. But during every emotional uncoupling comes the point where y'all gaze into the mirror, stick your finger in your reflection's breast, and tell them to end being such a impaired, whiny baby. —Peters

38. "Needed Me," Rihanna

Most heartbreaking lines: "Fuck your white horse and a carriage / Bet you never could imagine / Never told you lot you could have information technology / You needed me"

This song is and then petty and I honey it. Rihanna basically fabricated a hit off the "Sike, you thought!" meme and DJ Mustard added an unforgettable beat behind it. This is i of those bangers that y'all and your girls blast post-breakup, pre-going-out. Then, after you all sing in unison: "Don't become it twisted / You was merely another nigga on the hit listing / Tryna fix your inner issues with a bad bowwow," you all burst into laughter thinking about the man who is now barely a memory. Rihanna's confidence and savageness is actually on an untouchable level. (Retrieve, this vocal is on the same album where she sings "sexual practice with me is then amazing" over and over.) Long may she reign. —Jordan Ligons

37. "Then Sick," Ne-Yo

Most heartbreaking line: "Gotta change my answering machine, now that I'1000 lonely / 'Cause correct at present it says that we can't come to the phone"

The earworm of a generation! Ne-Yo said no to sappy ballads in more than ways than 1 with "So Sick," giving usa an R&B blast hitting for everyone sick of regular, schmegular love songs. Set to the world's catchiest beat out, Ne-Yo mourns a past relationship and all the day-to-twenty-four hours changes that come with moving on. "Gotta change my answering machine, now that I'm alone / 'Cause right at present it says that nosotros tin can't come up to the phone … Gotta fix that agenda I have that's marked July 15 / Because since in that location'southward no more you, there's no more anniversary." Fifteen years after, we even so can't turn off the radio. —Halliwell

36. "We Vest Together," Mariah Carey

Most heartbreaking line: "When you left I lost a part of me / It's still then hard to believe / Come back baby, please / 'Cause we vest together"

*Sighs.* This is hands the most played-out, sad breakup song of the early 2000s. Anybody 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 will glaze over, guaranteed. When the first 2 seconds of the infamous vanquish come through my speakers, I'm already changing the station. It's just so abrasive, and so Mariah.

You may think that yous won't find someone else to lean on when times become rough or someone to talk to you on the telephone until the sun comes upwardly, but let me tell you, y'all will and you'll be fine. Breakups suck, only delight don't torture your broken heart (or your ears) by listening to this vocal on echo. —Ligons

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

Near heartbreaking line: "Say for me that I'm all right, though things get kind of slow / She might think that I've forgotten her, don't tell her information technology isn't so"

The inspiration for Bob Dylan's masterful Blood on the Tracks has always been debated. Critics take long assumed that the album is near Dylan'southward separation from his wife, Sara. The couple's son, Jakob, reportedly believes that Blood is about his parents. But Dylan himself has steadily denied that his masterpiece is autobiographical, even proverb 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 thing. Claret strikes such a chord because the heartache information technology mines feels at one time deeply personal and universal.

That'southward near palpable on "If You lot See Her, Say Hello," which brings us into a fractured relationship in a style that'southward both effortlessly relatable ("We had a falling out, like lovers often will") and hyper-specific ("And to remember of how she left that nighttime, information technology still brings me a chill"). Information technology's not Dylan'due south flashiest or heaviest or all-time vocal, merely it is my favorite, a gentle, intimate portrait of lost love and lasting anguish. Like so much of his best work, it's propelled by its poesy, the raw insights most how it feels to be alive. The song cycles through the same phases that so many of u.s.a. do while processing heartbreak: denial, despair, anger, desire. Information technology floats on a electric current of remorse ("Sundown, yellowish moon, I replay the by / I know every scene by center, they all went past so fast") yet manages to convey the kind of longing that leads, charily, back toward hope ("If she'southward passing dorsum this manner, I'm not that hard to find / Tell her she tin can wait me upwards, if she's got the fourth dimension"). After enough listens, and enough heartache of your own, you lot realize that "If Y'all See Her, Say Hi" isn't really a breakup song. Information technology's a beloved letter. — Mallory Rubin

34. "Don't Wait Back in Acrimony," Oasis

Most heartbreaking line: "Stand up abreast the fireplace / Take that look from off your face / 'Crusade you ain't ever gonna burn my centre 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 Wait Back in Acrimony." I don't call up why, but it cemented this vocal (at least for me) as a ballad of communal weltschmerz, rather than personal sadness or regret, similar a fin-de-siècle "You'll Never Walk Alone." (For instance: "Don't Look Back in Anger" became a kind of unofficial anthem after the Manchester bombing in 2017.) Oasis knows a matter or ii well-nigh writing for the communal sing-along, the importance of the languid, memorable melody and the propulsive chord modify—this song would carry about the same emotional weight if information technology were just a title and a chorus. —Baumann

33. "Every Breath You Accept," the Law

Most heartbreaking line: "Since you've gone I've been lost without a trace / I dream at night, I can simply see your face"

This spectacularly maudlin New Moving ridge ballad, which anchored the Police'southward 1983 goliath Synchronicity and reigned as one of the biggest radio hits of the decade, is creepy as all hell, very much past pattern: an unrepentant stalker manifesto that doesn't so much draw spurned dear in terms of surveillance equally it describes full state surveillance in terms of spurned love: "Every move you make / Every vow you break / Every smile you fake / Every merits y'all 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 so cold and I long for your em-brace." Fun fact: He started writing the song at Ian Fleming'southward writing desk on the James Bond author'southward luxe Jamaican estate, which might not be creepy, but it'due south certainly weird. —Harvilla

32. "Don't Speak," No Doubt

Nearly heartbreaking line: "As we die, both you and I / With my head in my easily, I sit down and cry"

I mean, honestly, it takes a lot of guts to drop a Spanish classical guitar solo in the middle of an angsty '90s alt-stone song. It also takes a lot of guts to write a song about breaking upwards with the bass player in your band and then make a music video for the song that has shots in information technology like the 1 beneath: Don't speak, literally.

No Doubt'southward first striking is a work of art, total of raw, youthful emotion and circuitous arrangements. Information technology'southward cute, fell, painful, and incendiary, all at once. —Gruttadaro

31. "Thinkin Bout You lot," Frank Ocean

Most heartbreaking lines: "Do you not call up so far ahead? / 'Cause I been thinkin' bout forever"

Sometimes you have to lie to yourself to get through heartache. They weren't good enough for me. I can do ameliorate. I didn't love them, I simply idea they were cute. Frank Ocean'due south "Thinkin Bout You" exposes that kind of posturing for what information technology is: a facade. No, I wasn't crying about you, and past the way, I also own waterfront holding in Idaho. Frank'southward clearly still hung upwards on the past fifty-fifty if his onetime flame isn't. And the only style to work through the pain is to drop the lying and come up make clean with himself. Information technology's tender, information technology'southward sweet, only most of all, it's honest. —Sayles

30. "I'1000 Goin' Down," Mary J. Blige

Most heartbreaking lines: "Why'd yous accept to say bye? / Wait what you've washed to me / I can't cease these tears from fallin' from my eyes"

No matter your current relationship status, y'all will for certain sing your center out when this song comes on. I do not intendance, I am Mary J. when the chorus hits. By the cease of the song—a cover of Rose Royce's 1976 unmarried—yous've "gone down" so much that you lot're on the floor, eyes closed, hoop earrings in, and belting, "My whole world's up-[dramatic pause]-side downward!" I can't exist the only i, correct?

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

29. "Nothing Compares 2 U," Sinéad O'Connor

Nigh heartbreaking lines: "I could put my arms around every boy I see / But they'd merely remind me of y'all"

Breakups are freeing; breakups are imprisoning. When yous come out of a yearslong relationship, you have to relearn how to live without that person in your life. Parts of that process are beautiful—reconnecting with old friends, picking upwardly a new hobby, shaking off the shackles. But the breakup sticks with you. You run into your ex's best friend at the bar, or y'all hear a vocal that you both loved. Sometimes, it'due south a minor annoyance. Other times, it'due south an earth-shattering event. You're relearning how to live, but living is hard.

I can't recollect of a song that better captures that duality than "Nothing Compares 2 U," the 1990 O'Connor striking originally penned by Prince in 1985. You can exercise any you want: You can party all night, y'all can eat at a fancy restaurant, you can put your arms around all the boys and girls y'all'd like, simply it doesn't matter. It'south not them, and nothing will be. Your best hope is simply giving in and living for yourself. —Sayles

28. "Marvin's Room," Drake

Most heartbreaking line: "The woman that I would attempt / Is happy with a adept guy"

Drake is at his all-time when he'southward subversive because 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 risk. Drake pauses, so goes full Drizzy Deleterious: "Merely I've been drinkin' so much / That I'ma call her anyway." He gain to tell her that the human she's with isn't good enough to supplant what they had. It'due south the archetype overstep from an ex, simply the longer he goes on, we realize it's more near his pride and conflicting emotions about his life choices than it is about her. Drake spirals, telling her he's "had sexual practice four times this week / I can explain," that he's sponsoring women, that he tin't stop partying and request for naked pictures. Exactly what your ex-girlfriend wants to hear, I'grand sure. At least at that place'due south a voicemail interlude. —Haley O'Shaughnessy

27. "Simply a Friend," Biz Markie

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

Turns out this woman did non have what Biz Markie needed. Every bit he singsplains, he became kitten smitten with a adult female at one of his shows. Yous'd think that this would take happened to him all the fourth dimension, but information technology did not. This was "the first girl I ever talked to," Biz told EW concluding year. "Every fourth dimension I would call out to California, a dude would choice upward and paw her the telephone. I'd be like, 'Yo, what's up [with him]?' She'd say, 'Oh, he'southward simply a friend. He'due south nobody.'" Non taking the hint, Biz flew out to California to surprise her a week earlier than planned. When he showed up, at that place was a guy "tongue-kissing my girl in her mouth."

Biz. My guy. Sit downwards. Allow'south talk. First off, she was not your daughter. You met her ane time. Second, you lot 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 well-nigh his predicament. Yous know, a friend. —Danny Heifetz

26. "Burn," Usher

Most heartbreaking line: "But yous know, gotta allow information technology get / 'Cause the party ain't jumpin' like it used to / Even though this might trample you / Permit it burn down"

I couldn't imagine someone breaking upward with me with the lyrics to this song. Usher is all over the identify. He says he loves me, only our relationship has to come to an terminate; he says he's hurting and he's not happy, but he's breaking down and crying. Deep down he knows it'south best, but he hates the idea of me existence with someone else. Get your shit together, Usher!

Withal, for all of its confusing dorsum-and-along, this is a breakup classic. It preaches the ideology of forcing yourself to let go even when you don't know what you're going to do without your boo. After a heartbreak, anybody has constitute themselves teetering on the line between regret and freedom. Usher's "Burn" allows you to tap into that while simultaneously yelling out, "It'due south been fifty-eleven days, umpteen hours, and Imma be burnin' till you render!" —Ligons

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

Most heartbreaking line: "Simply each time I tell myself that I, well I tin't stand up the hurting / But when you hold me in your arms, I'll sing it one time again"

If yous're ever at your wits' end, tragically obsessed with someone who treats you like shit, you can notice some catharsis in the controlled chaos of Janis Joplin's song performance on "Piece of My Middle." Go ahead and scream along. You won't sound as good as Janis, simply you'll certainly experience a hell of a lot better afterward.

Once your acrimony fades a little, you lot can switch over to the original recording of this vocal, released a year earlier in 1967 and sung past Erma Franklin (yes, that's Aretha'south older sister). Or if yous need some more twang accompanying your despair, you can try the Religion Hill version. I likewise won't approximate y'all if the only person who can ease your pain is Shaggy (or Beverley Knight, Melissa Etheridge, Steven Tyler, Kelly Clarkson, or one of countless other artists).

Written by Jerry Ragovoy and Bert Berns, "Piece of My Heart" is one of the nearly relatable and enduring songs about Some Fuckboi in the history of fuckbois. The phone call-and-response structure of the chorus builds those simmering resentments and releases them with a abrupt, primal cry. Undoubtedly, there will be new versions of this song until the finish of time⁠—considering it'southward an absolute banger—but also because … men. —Matt James

24. "Skinny Love," Bon Iver

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

A good rule for breakup songs is that there has to exist a part that you lot can yell along to, unencumbered by lightheaded things similar constraint and self-awareness. The chorus of Bon Iver's "Skinny Dear" has a great 1, especially for anyone who'due south just exited a human relationship and feels compelled to heap all the blame on the other party.

You know the story past now: In 2006, Justin Vernon broke upwards with his girlfriend, packed up his car, and drove into the Wisconsin wilderness, emerging only afterwards recording an album of weepy breakup songs. That origin tale has been repeated then oft that it's go soft mush, obscuring the real truth: That For Emma, Forever Ago—and especially "Skinny Dear"—are profoundly cogitating, intelligent, moving documents about the breakdown of a relationship. —Gruttadaro

23. "Concur Up," Beyoncé

Nigh heartbreaking line: "Can't you run across at that place's no other homo above you? / What a wicked style to care for the girl that loves you"

It'southward difficult to express real hurt over an uptempo beat and make the heartbreak disarming. Yet Beyoncé is believable in "Hold Up," a painful bookkeeping of the emotions that come after discovering that your partner has cheated. Lemonade was inspired past truthful events—i.e., it's Beyoncé coming to terms with Jay-Z existence unfaithful. Adultery brings on a very specific type of devastation: Y'all're mad; you're miserable; y'all're humiliated. Y'all switch from ane emotion to another in a matter of minutes. She opens the song with confidence: No other adult female can give what she can. "Agree up, they don't love you like I love you." In a jiff, she'due south less certain of herself: "What'south worse, looking jealous or crazy?" Beyoncé settles on crazy, then returns to anger. "You let this good love become to waste." —O'Shaughnessy

22. "Cry Me a River," Justin Timberlake

Nearly breaking lyric: "Y'all didn't know all the ways I loved you, no / So you took a chance / And made other plans"

Entering 2002, Justin Timberlake wasn't regarded as much more than a teeny bopper. His group 'NSync was 1 of the defining groups of the boy band era, and he was its charismatic face. (The beautiful one, 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. And so the couple broke up, JT split from 'NSync, and "Cry Me a River" happened.

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

21. "With or Without You," U2

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

Nothing changes if nothing changes, as they say, and "With or Without Y'all" exists in that hopelessly recursive "I hate that I beloved yous" space. This song was U2's first no. 1 striking in the U.S., fifty-fifty though, Bono has said, "information technology's a very odd-sounding song … information technology kind of whispers its way into the globe." But information technology's non the whispers that resonate most, however, it'due south all those wails, like the crescendo of Bono's aching, eminently singalong-able ahhh-ahhh-ahh-ahhhhhs, or the painful, everlasting notes from the Border'southward "infinite guitar," engineered to agree a tone as if information technology were a grudge. "Psychotic restraint" is how Bono characterized the Edge's spare work on this track, a description that could double as breakdown advice. —Katie Baker

20. "Jolene," Dolly Parton

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

While other female country singers might've handled their man's newfound fascination with a beautiful redhead by, say, excavation a cardinal into the side of his pretty lilliputian souped-upwardly four-cycle drive, or—just spitballing hither—threatening to ship her to Fist Urban center, Parton simply pleads for mercy. The desperate pitch of her appeal, set against a frantic Dorian-style guitar riff, sets the stakes far higher than those you might detect in generally stern country songs well-nigh cheatin', lyin', and being untrue. Any armchair scholar of Parton's work can tell yous she cloaks feminist manifestos inside marketable diddies nigh everyday experiences. I've always taken the vocal's urgency to imply something that every woman learns eventually: Relationships can exist both romantically fulfilling, and, too frequently, an economic lifeboat to a amend life. In "Jolene," our narrator isn't just grasping onto her homo, she's grasping for survival. —Alyssa Bereznak

xix. "I Heard It Through the Grapevine," Marvin Gaye

Most heartbreaking line: "Do you plan to permit me go / For the other guy you loved before?"

This song was first released by Gladys Knight and the Pips in 1967. A year later Marvin Gaye released a slower version of it on his album In the Groove. Mayhap the song resonated with Gaye considering he married a 41-year-old woman when he was but 24, and their marriage was total of infidelities. "I was in honey with the thought of love," Gaye once said. Or at least that's what I heard through the grapevine. —Heifetz

18. "Ex-Factor," Lauryn Hill

Most heartbreaking line: "Where were you when I needed y'all?"

"Ex-Gene" is more than a breakdown song, it's near recognizing a toxic relationship earlier you have the words to phone call it a toxic relationship. Each line, so honest information technology hurts, is about the fruitless search for reason in a scenario devoid of information technology. Hill's lyrics capture the worst of the worst of a human relationship on the rocks: the pain, the complicity, and the unwillingness to give up on a dear you lot recollect is still there, buried below the bullshit.

When it hit airwaves once again in 2018 on Drake'south pandering notwithstanding irresistible "Nice for What," information technology was almost like recognizing and reclaiming a by self—one who might have cried forth to the original. Now, equally wiser, more than Empowered™ listeners, we heard the remixed, tricky claw devoid of its devastating verses and bopped our heads as Drake reminded the states of how short life is. Still, no 1 can capture the raw, uncomfortable emotion that Lauryn originally did—and no ane ever volition. —Johnson

17. "Yous're And then Vain," Carly Simon

Most heartbreaking line: "Well, you said that we made such a pretty pair / And that you lot would never leave / Simply you gave away the things you loved / And one of them was me"

Far before Taylor Swift sent her fans on subtweet scavenger hunts, Carly Simon penned a ballsy kissoff that, thanks to its self-referential chorus, left the world wondering whom information technology was nigh and what they could've possibly done to anger her. More than 40 years of speculation afterward, we now know that the vocalist was describing the actor Warren Beatty. (She added in a contempo, withering interview that, although the song describes iii carve up men, Beatty "thinks the whole affair is well-nigh him.") We may never know what visitor he kept (cough: Mick Jagger?), but the lasting power of Simon's clear-eyed takedown stands equally a referendum on the unchecked male ego, whether its independent in the trunk of a dashing actor or a moody fuckboy. —Bereznak

16. "Dancing on My Own," Robyn

Nigh heartbreaking line: "Yeah, I know information technology's stupid, I merely gotta see it for myself"

Last year, following a Robyn show at Madison Square Garden, elated concertgoers continued the party on the A/C/E train subway platform, breaking into a giddy public performance of "Dancing on My Own." You wouldn't typically await a breakup song to be the 1 that leads New Yorkers to such displays of collective joy, merely most breakup songs aren't like this one: a song you can strut to, a club canticle, a scene-stealer, a story of lonesomeness that still finds its solace in a oversupply. It's a song near moving on—I just came to say good day—but also about, just, moving. The singer might exist alone in the corner, and she might know information technology's stupid, but she'south out in that location dancing, at least. —Bakery

15. "Thank U, Side by side," Ariana Grande

Almost heartbreaking line: "Wish I could say, 'Thank you' to Malcolm / 'Cause he was an affections"

This song is a decision to be done with suffering over a human relationship, to recommit to oneself, to focus on healing and establishing new patterns. To not only rehearse past losses just to envision futurity victories, and besides to live in the moment, to be here now.

This to do the actual, 24-hour interval-in, day-out work of being happy. —Peters

14. "Terminate of the Road," Boyz II Men

Well-nigh heartbreaking line: "Information technology'due south unnatural"

Both the joyous genesis and abject death knell for billions of '90s junior-loftier-gymnasium-dance relationships that only lasted the length of the song itself, "End of the Road," which rose to power on 1992'due south Boomerang soundtrack, is one of the biggest hits in popular-music history. Like, "thirteen straight weeks atop the Hot 100" big. Like, "The 'Old Town Road' of Its Day" big, a tearjerking shout-forth canticle for lovelorn belters likewise devastated to even take their horses and leave the business firm. The final a capella chorus is a signature moment in American cultural history, at once exhilarating and devastating: "Information technology'due south unnatural / You lot belong to me / I vest to you." The word unnatural has never sounded and so natural, and so miserable. —Harvilla

13. "Dreams," Fleetwood Mac

Near heartbreaking line: "Now here you go once again, you say you desire your freedom / Well, who am I to keep you down?"

Even 40-plus years on, to hear Stevie Nicks softly moaning, "What yous had ... and what you lost / And what y'all had ... and what you lost" to the guy playing guitar is to live forever, and to imagine that guitar player dropping dead from remorse on the spot. (Lindsey Buckingham, of class, has been known to belt out a sweetly caustic breakdown anthem or 2 himself.) Equally the second (and best!) runway on 1977's zillions-selling Rumours, "Dreams" is both radically overexposed and however somehow criminally underrated, fixed to its iconic place, time, and circumstances just besides shockingly timeless. (Zoë Kravitz rhapsodizes information technology in the airplane pilot of Hulu's new High Fidelity remake series to evidence her rock-nerd bona fides.) Pair information technology with "Silvery Springs" for maximum effect. —Harvilla

12. "How Can Yous Mend a Broken Middle," Al Green

Most heartbreaking line: "Let me live over again"

At that place's heartbreak, and then there's Al Greenish heartbreak. (Not to slight the original Bee Gees version—Green is all I know when I'm going through it.) He'due south exasperated from the beginning, 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 y'all mend a cleaved heart? / How can you cease the rain from falling downwardly? / How tin can you cease the sun from shining? / What makes the world go round?" Green is begging for answers, for "somebody, please" to come up set him. He pleads, "Permit me live over again." Life as he knew information technology is over without this person, and every bit long as the song is on, it feels over for us, likewise. —O'Shaughnessy

11. "Torn," Natalie Imbruglia

Near heartbreaking line: "I'1000 all out of faith / This is how I feel, I'k common cold and I am shamed / Lying naked on the floor"

There'southward a bad breakup, at that place's stone bottom, and so at that place's existence "cold and shamed, lying naked on the floor." Natalie Imbruglia'south 1997 1-hit wonder (and sneaky comprehend) doesn't mince words in describing exactly how shitty it feels to put your faith in the incorrect man. (Or whatsoever man, depending on how hard you vibe with this vocal.) "Torn" has taken a turn for the over-covered and over-memed these days, but you're lying if you say you don't still hit that chorus every time. —Halliwell

10. "I Will Survive," Gloria Gaynor

Most heartbreaking line: "And so you felt like dropping in and just wait me to exist gratis / Well now I'm saving all my lovin' for someone who's lovin' me"

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

nine. "Own't No Sunshine," Bill Withers

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

To make a vocal from 1971 about a video game from 2010: Dante's Inferno is an RPG based loosely on the outset canticle of the Divine One-act. I say loosely because EA Dante has rippling muscles and a massive scythe, his only protections confronting the legions of the night, who've stolen his dearest Beatrice. I never played it, but a friend who did described his frustration with the game: It's as if its decision got further abroad the more time he devoted to it. A Super Bowl commercial showed Dante sprinting toward Hell's gaping mouth determined but, yous know, definitely doomed. As he descends you hear the low croak of Beak Withers'southward voice, pining after a lost lover: "Ain't no sunshine when she's gone, only darkness everyday." My last breakup didn't involve a behemothic flaming devil monster, but it did feel like a similarly hopeless uphill boxing. —Peters

8. "Someone Similar Yous," 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 get much better than "Someone Similar Yous." Adele's ode to the one who got away is perhaps the near universally adored tearjerker of the by decade; starting with that uncomplicated pianoforte line and catastrophe in that crushing hook: "Sometimes it lasts in love, merely sometimes it hurts instead." And of course, that voice! Watching the unproblematic blackness and white music video now, it's hit how baby-faced Adele was at 21, despite her delivery of a song that displays so much emotional maturity. She wishes the best for her ex ("Old friend, why are y'all so shy?"), just damn, she'due south still hurting. Aren't nosotros all! —Halliwell

vii. "I Desire Y'all Dorsum," The Jackson 5

Most heartbreaking lyrics: "Someone picked you from the bunch, i glance was all it took / Now it's much besides belatedly for me to have a second await"

Perhaps the nearly outwardly joyous song in this entire ranking, "I Want Yous Back" spins a tale that anyone who's e'er taken someone for granted will understand. An 11-year-old Michael Jackson is at his nearly precocious here, singing about the girl whom he didn't fully appreciate until someone else stole her heart. At present he just wants another adventure to bear witness that he knows how to treat her right. Michael, of course, didn't write the song—it was penned by Berry Gordy and Co.—but he sells it in a way that someone 2 or three times his age never could. A leopard can't change its spots, but if it sounds this expert trying to convince you it tin, why not give it i more chance? —Sayles

6. "Since U Been Gone," Kelly Clarkson

Most heartbreaking line: "How come I'd never hear you say / 'I simply wanna be with you' (be with you) / I gauge you never felt that way"

At that place is a moment in every breakdown where, after a few weeks of self-pity, you shed your sweatpant cocoon, step outside, and, with the instantaneity of a rubber band snap, suddenly know deep within your eye that your ex was an insufferable blowhard. Kelly Clarkson'southward mosh-adjacent ability pop ballad embodies the newfound self-assurance that comes with that realization. It also happens to exist enshrined in a popular culture moment that I will forever associate with existence a melodramatic 16-year-sometime millennial: "Since U Been Gone" was written by pop lords Max Martin and Dr. Luke, who ripped its entire musical structure from the far more than poetic Yeah Yeah Yeahs hit, "Maps," and so—after being passed upwards by both Pink and Hilary Duff—was sung by the very outset winner of the then-fledgling reality TV show American Idol. The AIM-friendly "U" in the title is simply the icing on the cake. —Bereznak

v. "Ms. Jackson," Outkast

Nigh heartbreaking lyric: "Forever never seems that long until y'all're grown / And discover that the day-by-day ruler can't be besides incorrect"

Sometimes breaking upwardly with your pregnant other's family is just as difficult every bit breaking upwards with them. Big Boi and André 3000 understood that on "Ms. Jackson," a vocal defended to Kolleen Maria Wright, the mother of Erykah Badu, with whom André had a child. Three Stacks's verse is specially poignant—his intentions were proficient, but things took a turn for the worse. It'south a harsh reality: Most relationships are born with an expiration engagement, no matter how vivid the flame burned at the get-go. Equally far equally 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 Ever Love You," Whitney Houston

Most heartbreaking line: "Delight don't cry / We both know I'm not what you, you need"

Dolly Parton wrote one of the near dynamic dear songs ever with "I Will Always Love You." Whitney Houston, who sang a comprehend for the movie The Bodyguard, made a worldwide hit with her phenomenal range. Both versions are wonderful for unlike reasons, though Parton's honeyed, wobbly original is all-time for heartbreak. For i, information technology'southward accurate: She wrote the song for her former manager and professional partner, Porter Wagoner, afterward she decided to go out him. Parton is sympathetic, notwithstanding determined to go. Every bit she sings in the bridge, it's bittersweet. They are both better off this way, she argues, simply wishes him nothing but "joy and happiness." One of the hardest relationship lessons is that two people can love each other and it withal non be right for either—thanks to Dolly and Whitney, it was one learned early on. —O'Shaughnessy

3. "I Can't Make You Love Me," Bonnie Raitt

Virtually heartbreaking line: "I'll close my eyes / Then I won't encounter / The dearest yous don't feel when yous're belongings me"

You might be a girlfriend, a husband, a partner, or even a friend with benefits. Whatever role yous play in service of love, it comes with a characterization that sets expectations. There is clarity and comfort in knowing where yous stand with someone. But despite all of our semantics and promises, the terrifying reality of our dearest lives is that love itself tin can be a ruthlessly nonbinding understanding, an at-will arrangement. Even more frightening is that it's often our hearts—non united states of america—calling the shots.

What sets "I Can't Make You Love Me" autonomously from most breakdown songs is that it takes place at the about painful signal of a breakup: acceptance. It's non a post-breakdown anthem of empowerment or a desperate plea to stay together. It's the total forcefulness of the disorienting 1-two punch of loss and loneliness. It'southward the globe-shattering moment when you give upwardly the fight.

Bonnie Raitt'southward absorbing performance of this song (written by Mike Reid and Allen Shamblin) carries the weight of a lifetime in and out of love. She sets down her slide guitar, sits Bruce Hornsby downwards at the pianoforte, 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 first take. "I Tin can't Make You Love Me" has been covered past countless artists, included on several Greatest Songs Of All Time lists, and inducted into the Grammy Hall of Fame.

The songs that affect usa nigh deeply are the ones that unite united states through the most man of shared experiences. Somewhen, we all learn that you can't make someone'due south heart feel "something information technology won't." But should you one day notice yourself at rock bottom, suddenly alone in darkness—whether it's your offset time or your 14th—yous can feel a little bit less lonely knowing that Bonnie's been there, too. —James

2. "You Oughta Know," Alanis Morissette

About heartbreaking line: "Does she know how yous told me yous'd concord me until you lot died, till you died / Merely you're still alive"

Alanis Morrisette was 19 years old when she recorded that ballad of bitterness "Yous Oughta Know" in one accept at 11 p.m. "All those vocals are just her at the end of the night," said her cowriter Glen Ballard in an oral history of the album Jagged Little Pill, "singing something she but wrote." The result was a revelation in its ragged emotion, all fingernail scratches and fellatio, a work of art centering the seething spirals of rage. (That it was mayhap inspired by Uncle Joey remains both iconic and deeply weird, but also makes ill sense: You lot haven't truly been jilted until you've been jilted by someone who's not even that absurd, you know?) "You 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 could you want—other than sugariness, sugariness vengeance? —Baker

1. "Majestic Rain," Prince

Most heartbreaking line: "I never meant to cause y'all whatsoever sorrow / I never meant to cause you any pain"

Purple rain, according to an unsourced quote that'southward widely attributed to Prince Rogers Nelson, is the effect of blood mixing with the sky, which is a sort of apocalyptic drama that only Prince could conjure. But you don't even demand to understand what purple rain is to feel "Purple Rain," a power ballad to cease all ability ballads.

Some breakup songs are mean, some are mournful, others are empowering. Merely "Purple Rain" has the power to experience like everything all at one time, a near-religious experience of a song that has the ability to heal like no other. In times of problem, put "Purple Rain" on, and let him guide you lot. —Gruttadaro

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