Hes Doing It to Me Again

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 it be for the lone, like Carole King'south "Information technology's Too Late" or Bob Dylan'southward "If You See Her, Say Hello"? Does it have to address the breakup 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 "Weep Me a River" or any track off of Rumours?

Nosotros here at The Ringer believe that since heartache comes in many forms, so should the breakdown song. And in accolade of Valentine's Mean solar day, we decided to dig deep into the genre. Below, you lot'll discover our ranking of the 50 greatest breakup songs of all time, as voted on by our staff. The list spans several decades and many unlike moods, only all are rooted in some type of pain. In that location was only one rule for the final ranking: just one song per creative person was included to avoid Dolly Parton or fifty-fifty Drake from dominating.

So if you're lonely, fire upward our playlist and cry along every bit you read our thoughts on each entrant. If you're happily attached, you can still dive in—these are some of the greatest songs e'er recorded, and that'southward true whether you're in your feelings or not. Maybe y'all'll gain a greater appreciation for your current relationship. Subsequently all, breakup songs resonate only when you know what it'south like to lose in love. —Justin Sayles

l. "Nosotros Are Never Ever Getting Back Together," Taylor Swift

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

One of the most savage breakup songs in history, "We Are Never Ever Getting Back Together" encapsulates the severe "fuck that guy!" energy that follows a long-overdue parting of ways. Nosotros've all had that post-fight rant with our friends: "Ugh … so he calls me upward and he's similar, 'I all the same beloved you,' and I'm like … 'I simply … I mean this is exhausting, y'all know, like, we are never getting back together. Similar, e'er.'" Flippant, triumphant, and entirely wearied by All Men, Taylor Swift gave us the perfect soundtrack for breakup recovery. — Kate Halliwell

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

Nearly heartbreaking line: "I demand somebody and always / This ill strange darkness / Comes creeping on so haunting every time"

"I Miss You" is similar a minimalist/emo take on Meat Loaf. It rules. The two best things well-nigh this number are Travis Barker'southward simple simply persistent drumbeat and Tom DeLonge's entrance on the 2nd poesy. It'south part of the grand pop punk tradition of showing y'all mean business organization by going upwardly an octave, of which "I Miss You lot" (along with the Starting Line'due south "The Best of Me") is the exemplar.

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

48. "It's Too Belatedly," Carole Rex

Nearly heartbreaking line: "Simply nosotros but tin't stay together, don't you feel it, too? / Still I'1000 glad for what we had and how I once loved you"

"It's Too Late" is a crushing ode to the virtually mutual kind of breakup. The natural procedure of two people growing apart is every bit heartbreaking equally it is commonplace, and King sings in a tone perfectly situated between her sorrow and the shrugging admission that "we actually did effort to brand it." Her conversational delivery early on in the song brings usa into the living room, diner, or sidewalk where "the talk" between her and her virtuallyhoped-for-ex is happening: "One of united states of america is changing, or peradventure nosotros just stopped trying," she sings, plainly laying out the central, blameless reasons for why most people end up separating. The vocal is defined by its maturity and its conciliatory attitude, just equally with actual breakup conversations, that doesn't make information technology any easier to hear. —Cory McConnell

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

Near heartbreaking line: "I can't forget the mean solar day you left / Time is then unkind"

This is a perfect instance of the kind of breakup song you hear on the radio (or, in the tardily '90s, perchance the club—the Frankie Knuckles business firm remix still goes) and, on a normal mean solar day, just hear some other pop song, but when you're experiencing heartache, what originally sounded similar songwriting clichés go the truest words you lot've ever heard. "I have cried a lot of nights," you think, getting out of bed for the starting time time in days to grab a coil of toilet newspaper since you ran out of Kleenex. "Life is savage without you here abreast me," you murmur, staring into the dour chasm of loneliness you at present know every bit life. "I would literally do anything on God'southward green earth to hear you lot say you dearest me again," yous realize with the greatest clarity you've ever experienced. Anyway, where are my altos at? This is our karaoke song. — Kjerstin Johnson

46. "Mr. Brightside," the Killers

Near heartbreaking line: "Now they're going to bed and my stomach is ill / And it's all in my caput"

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

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

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

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

44. "Tyrone," Erykah Badu

Most heartbreaking line: "I just want it to be, you and me, like it used to be, infant / But ya don't know how to act"

The second-all-time moment on this viciously sultry slow jam, the crown gem of Erykah Badu'southward 1997 album Live, is the stupendous opening line: "I'grand gettin' tired of your shit / You lot don't ever buy me nothin'." The first-best moment is all the women in the crowd immediately shrieking with please and, one fears, recognition. "Tyrone" is named for one of an unnamed deadbeat lover'due south numerous deadbeat friends: "Every fourth dimension nosotros become somewhere," Badu purrs with lethal authority, "I gotta reach down in my purse / To pay your way and your homeboy's mode and sometimes your cousin'southward way." Information technology is the gender-flipped riposte to Friday'south "Adieu, Felicia," and in fact turned up as a joke in 2000's Next Friday; it "followed me thru my career like an obsessed X boyfriend," equally 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. "Beloved Is a Battlefield," Pat Benatar

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

The agonizingly propulsive signature hitting from flamethrower-voiced '80s pop queen Pat Benatar laments non then much a breakup equally a near-breakup in progress, an acknowledgement that truthful beloved ways near breaking up pretty much all the fourth dimension: "Believe me / Believe me / I tin't tell you why / Just I'chiliad trapped past your beloved / And I'one thousand chained to your side." Information technology'due south a karaoke classic you have no business attempting, a cheeseball Reagan-era smash of eternal profundity, and a hit annunciation that sometimes the only thing worse than splitting upwardly is not splitting up: "Do I stand in your way / Or am I the best thing yous've had?" she wails with genuine desperation, and the reply, of course, is both. —Harvilla

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

Most heartbreaking line: "Throwing shit around, the whole identify screwed up / Maybe I should call Mase then that he could pray for us"

We're not even talking near the whole song—we're talking about 20 or and so seconds of Bink production after Kanye's 2nd verse, but earlier Rick Ross'due south only poesy, arguably 1 of the all-time in his career. In it, he describes West's near-fatal auto crash in 2002 every bit an aborted climb "up the Lord'due south ladder," and honestly, that'southward exactly what the collection of power strings audio like on this bridge. A climb upward the Lord's ladder, a departure from World, a one-way trip to anywhere but hither. —Micah Peters

41. "Suspicious Minds," Elvis Presley

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

You tin see the ripples of "Suspicious Minds" throughout the course of breakdown song history, from "Railroad train in Vain" to "Dancing on My Ain," which, yous know, information technology's Elvis. But across the juxtaposition of its relatively upbeat music and depressing-as-hell lyrics, I love the structure of this song, with a peppy guitar intro and verses that build into a chorus that goes from G major to very, very E minor and just doesn't ever really resolve. This might not be the only reason the song fades out simply there'southward no real suitable catastrophe signal for the terminal notes of the chorus, so it e'er drops back into a verse or a bridge or another chorus. "John Jacob Jingleheimer Schmidt" resolves more easily. Just like a broken relationship. —Baumann

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

Most heartbreaking lines: "Although she may be cute, she's just a substitute / Considering you're the permanent one"

On this classic Motown tearjerker, Smokey embodies the thought of the sad clown better than any vocal ever has. He'south the life of the political party—using jokes like a clown uses makeup—but inside, he's wounded, pining for a by lover. He's dating someone new, but he's not thinking of her. (Side notation: I don't know who I'g sadder for hither, Smokey or the rebound he's walking around boondocks with.) He may have wiped away the tears, but they've left their mark. And the makeup only makes the tear tracks that much more than apparent. —Justin Sayles

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

Most heartbreaking line: "And so this is inevitable withdrawal / Even if I stop wanting you / And perspective pushes through / I'll be some next man'southward other woman soon"

On "Tears Dry on Their Ain," Amy Winehouse demanded that Amy Winehouse take her own advice. "I cannot play myself over again, I should simply be my own best friend," she warns. "Not fuck myself in the head with stupid men." These lines that pried the song open were one of Winehouse's hallmarks every bit a writer—"Tears" begins in the dumps, in the aftermath. But during every emotional uncoupling comes the point where you lot gaze into the mirror, stick your finger in your reflection'due south chest, and tell them to stop being such a dumb, whiny baby. —Peters

38. "Needed Me," Rihanna

Near heartbreaking lines: "Fuck your white equus caballus and a carriage / Bet yous never could imagine / Never told you you could have it / Y'all needed me"

This song is so picayune and I dearest it. Rihanna basically made a striking off the "Sike, you thought!" meme and DJ Mustard added an unforgettable beat backside it. This is 1 of those bangers that yous and your girls blast mail service-breakup, pre-going-out. And so, later on you lot all sing in unison: "Don't get it twisted / You lot was but some other nigga on the hit list / Tryna fix your inner problems with a bad bitch," you all burst into laughter thinking about the homo who is now barely a memory. Rihanna's confidence and savageness is really on an untouchable level. (Remember, this song is on the same album where she sings "sex with me is so astonishing" over and over.) Long may she reign. —Hashemite kingdom of jordan Ligons

37. "So Ill," Ne-Yo

Virtually heartbreaking line: "Gotta change my answering machine, now that I'm alone / 'Cause right now it says that we can't come up to the phone"

The earworm of a generation! Ne-Yo said no to sappy ballads in more ways than one with "Then Sick," giving united states of america an R&B smash hit for everyone sick of regular, schmegular beloved songs. Fix to the globe's catchiest beat, Ne-Yo mourns a past relationship and all the twenty-four hours-to-twenty-four hours changes that come with moving on. "Gotta modify my answering machine, now that I'm solitary / 'Cause correct now it says that we can't come to the telephone … Gotta fix that agenda I have that'south marked July 15 / Because since there'due south no more y'all, there'due south no more than ceremony." Fifteen years subsequently, nosotros withal tin can't turn off the radio. —Halliwell

36. "We Belong Together," Mariah Carey

Near heartbreaking line: "When yous left I lost a function of me / It's all the same so difficult to believe / Come up back baby, delight / 'Cause we belong together"

*Sighs.* This is easily the most played-out, sorry breakup song of the early 2000s. Everyone idea about someone who could've/should've been their soul mate when this dropped in 2005. But now if information technology comes on the radio and you're either happily single or in a solid relationship, your optics will glaze over, guaranteed. When the starting time ii seconds of the infamous crush come through my speakers, I'm already changing the station. Information technology's just then annoying, and so Mariah.

Y'all may think that you lot won't find someone else to lean on when times go rough or someone to talk to you on the phone until the sun comes up, only let me tell yous, yous volition and yous'll exist fine. Breakups suck, simply please don't torture your broken center (or your ears) by listening to this song on repeat. —Ligons

35. "If You Come across Her, Say Hi," Bob Dylan

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

The inspiration for Bob Dylan'due south masterful Blood on the Tracks has always been debated. Critics have long assumed that the album is near Dylan'southward separation from his wife, Sara. The couple's son, Jakob, reportedly believes that Blood is well-nigh his parents. Merely Dylan himself has steadily denied that his masterpiece is autobiographical, even proverb instead that it's based on … Chekhov'southward 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. Blood strikes such a chord because the heartache it mines feels at once deeply personal and universal.

That's most palpable on "If You Run into Her, Say Hi," which brings united states into a fractured relationship in a way that's both effortlessly relatable ("We had a falling out, like lovers often volition") and hyper-specific ("And to think of how she left that night, it still brings me a chill"). It's not Dylan's flashiest or heaviest or best song, merely it is my favorite, a gentle, intimate portrait of lost love and lasting anguish. Like and so much of his best work, information technology'south propelled past its verse, the raw insights nigh how it feels to be alive. The song cycles through the same phases that so many of us do while processing heartbreak: deprival, despair, anger, desire. It floats on a current of remorse ("Sundown, yellow moon, I replay the by / I know every scene by heart, they all went by so fast") notwithstanding manages to convey the kind of longing that leads, cautiously, dorsum toward promise ("If she's passing back this fashion, I'm non that hard to find / Tell her she can look me up, if she'due south got the time"). Later enough listens, and enough heartache of your own, y'all realize that "If You Run across Her, Say Hello" isn't really a breakup song. It'south a love letter. — Mallory Rubin

34. "Don't Look Dorsum in Anger," Oasis

Well-nigh heartbreaking line: "Stand upward beside the fireplace / Have that await from off your face up / 'Cause yous ain't ever gonna burn my heart out"

The closest I've e'er come to living in an episode of Glee was when my loftier school French class spontaneously bankrupt out singing "Don't Look Dorsum in Anger." I don't call up why, only information technology cemented this song (at least for me) as a ballad of communal weltschmerz, rather than personal sadness or regret, like a fin-de-siècle "Y'all'll Never Walk Alone." (For example: "Don't Wait Back in Anger" became a kind of unofficial anthem later the Manchester bombing in 2017.) Oasis knows a thing or 2 about writing for the communal sing-along, the importance of the languid, memorable tune and the propulsive chord modify—this vocal would behave about the same emotional weight if information technology were just a championship and a chorus. —Baumann

33. "Every Breath Yous Take," the Constabulary

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

This spectacularly maudlin New Wave carol, which anchored the Police'due south 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 love in terms of surveillance as information technology describes full state surveillance in terms of spurned love: "Every move you make / Every vow y'all break / Every smile you fake / Every claim you lot pale." And so on. "I'll be watching you," Sting concludes a couple dozen times throughout, merely it'southward the chest-pounding bridge where the trio'south creepy-soulful frontman does some of his all-time belting, his all-time pleading, his best super-creepy emoting and enunciating: "I experience and 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 writer'south luxe Jamaican estate, which might non be creepy, but it's certainly weird. —Harvilla

32. "Don't Speak," No Doubt

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

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

No Doubt'south kickoff hitting is a work of fine art, full of raw, youthful emotion and complex arrangements. It's beautiful, cruel, painful, and incendiary, all at once. —Gruttadaro

31. "Thinkin Tour You," Frank Ocean

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

Sometimes you have to prevarication to yourself to become through heartache. They weren't proficient enough for me. I tin do amend. I didn't love them, I just thought they were cute. Frank Ocean's "Thinkin Bout You" exposes that kind of posturing for what information technology is: a facade. No, I wasn't crying well-nigh you, and by the way, I too own waterfront property in Idaho. Frank's clearly nevertheless hung upwards on the past even if his former flame isn't. And the only way to work through the hurting is to drib the lying and come up make clean with himself. It'due south tender, it's sweet, but most of all, it's honest. —Sayles

30. "I'k Goin' Downwardly," Mary J. Blige

Most heartbreaking lines: "Why'd y'all have to say goodbye? / Expect what yous've done to me / I can't cease these tears from fallin' from my optics"

No affair your current relationship status, you volition for sure sing your center out when this vocal comes on. I exercise non care, I am Mary J. when the chorus hits. Past the end of the song—a encompass of Rose Royce's 1976 single—you've "gone downwards" so much that you're on the floor, eyes closed, hoop earrings in, and belting, "My whole world'south upwards-[dramatic pause]-side down!" I can't exist the only one, correct?

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

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

Most heartbreaking lines: "I could put my artillery effectually every boy I run across / But they'd only remind me of you"

Breakups are freeing; breakups are imprisoning. When you come out of a yearslong relationship, you lot have to relearn how to alive without that person in your life. Parts of that process are cute—reconnecting with old friends, picking upwards a new hobby, shaking off the shackles. But the breakup sticks with yous. You run into your ex'due south all-time friend at the bar, or you hear a song that yous both loved. Sometimes, it's a small-scale annoyance. Other times, it's an earth-shattering event. Yous're relearning how to alive, simply living is difficult.

I can't think of a vocal that amend captures that duality than "Zilch Compares 2 U," the 1990 O'Connor hitting originally penned by Prince in 1985. You tin do whatever you want: You can party all night, yous tin swallow at a fancy restaurant, y'all can put your arms effectually all the boys and girls you'd like, merely it doesn't matter. It's non them, and nothing will be. Your best hope is just giving in and living for yourself. —Sayles

28. "Marvin's Room," Drake

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

Drake is at his best when he'due south destructive considering he masks the gaslighting with a softer sadness. "The woman that I would try / Is happy with a skillful guy," he sings. Is he happy for her? The lines suggest that there'due south at least a take chances. Drake pauses, then goes full Drizzy Deleterious: "Only I've been drinkin' then much / That I'ma call her anyhow." He proceeds to tell her that the homo she'southward with isn't expert enough to replace what they had. Information technology'southward the classic overstep from an ex, but the longer he goes on, we realize information technology's more virtually his pride and conflicting emotions about his life choices than it is about her. Drake spirals, telling her he's "had sex four times this calendar week / I can explicate," that he's sponsoring women, that he can't stop partying and asking for naked pictures. Exactly what your ex-girlfriend wants to hear, I'grand sure. At to the lowest degree there's a voicemail interlude. —Haley O'Shaughnessy

27. "Just a Friend," Biz Markie

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

Turns out this woman did not have what Biz Markie needed. As he singsplains, he became kitten smitten with a woman at one of his shows. You'd think that this would have happened to him all the fourth dimension, but it did not. This was "the first girl I e'er talked to," Biz told EW last year. "Every time I would call out to California, a dude would pick upward and hand her the telephone. I'd exist like, 'Yo, what'southward up [with him]?' She'd say, 'Oh, he's only a friend. He's nobody.'" Not taking the hint, Biz flew out to California to surprise her a calendar week before than planned. When he showed upwardly, there was a guy "tongue-kissing my daughter in her oral cavity."

Biz. My guy. Sit downward. Allow's talk. First off, she was not your daughter. You met her ane fourth dimension. Second, y'all did non take hold of her tongue-kissing a dude. You stalked her. Third, it was extremely obvious that this friend was not merely her friend. What Biz Markie needed was someone to listen to his story and requite him honest feedback nigh his predicament. You know, a friend. —Danny Heifetz

26. "Burn down," Usher

Most heartbreaking line: "Only y'all know, gotta let it go / 'Cause the party own't jumpin' similar it used to / Even though this might bruise you / Let it burn"

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

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

25. "Slice of My Heart," Big Blood brother & the Holding Company

Nigh heartbreaking line: "Merely each fourth dimension I tell myself that I, well I tin't stand the pain / Simply when y'all hold me in your artillery, I'll sing information technology once again"

If you're e'er at your wits' end, tragically obsessed with someone who treats you like shit, yous can find some catharsis in the controlled chaos of Janis Joplin'due south vocal performance on "Piece of My Middle." Go ahead and scream along. Yous won't audio as good as Janis, simply you'll certainly experience a hell of a lot better later on.

One time your anger fades a little, you tin switch over to the original recording of this vocal, released a yr earlier in 1967 and sung by Erma Franklin (yep, that'southward Aretha's older sister). Or if you demand some more twang accompanying your despair, you tin can try the Faith Hill version. I also won't guess you lot if the just person who can ease your pain is Shaggy (or Beverley Knight, Melissa Etheridge, Steven Tyler, Kelly Clarkson, or ane of countless other artists).

Written by Jerry Ragovoy and Bert Berns, "Piece of My Eye" is one of the most relatable and enduring songs about Some Fuckboi in the history of fuckbois. The call-and-response structure of the chorus builds those simmering resentments and releases them with a abrupt, fundamental cry. Undoubtedly, in that location volition be new versions of this song until the end of time⁠—considering it's an absolute banger—just also because … men. —Matt James

24. "Skinny Dearest," Bon Iver

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

A proficient dominion for breakdown songs is that there has to be a role that yous tin yell along to, unencumbered by silly things like constraint and self-awareness. The chorus of Bon Iver's "Skinny Honey" has a bang-up i, specially for anyone who's merely exited a relationship and feels compelled to heap all the blame on the other party.

You lot know the story past now: In 2006, Justin Vernon broke up with his girlfriend, packed up his motorcar, and drove into the Wisconsin wilderness, emerging just later recording an album of weepy breakup songs. That origin tale has been repeated so often that it's get soft mush, obscuring the real truth: That For Emma, Forever Ago—and especially "Skinny Love"—are profoundly reflective, intelligent, moving documents about the breakdown of a relationship. —Gruttadaro

23. "Hold Up," Beyoncé

About heartbreaking line: "Can't you see there's no other human to a higher place you? / What a wicked style to treat the daughter that loves you"

It's difficult to express real hurt over an uptempo trounce and make the heartbreak convincing. Yet Beyoncé is believable in "Agree Upwardly," a painful accounting of the emotions that come after discovering that your partner has cheated. Lemonade was inspired by true events—i.e., it's Beyoncé coming to terms with Jay-Z being unfaithful. Adultery brings on a very specific type of devastation: You're mad; you're miserable; you're humiliated. You switch from one emotion to another in a affair of minutes. She opens the vocal with confidence: No other adult female tin can give what she can. "Concord up, they don't dearest you like I beloved you." In a jiff, she's less sure of herself: "What's worse, looking jealous or crazy?" Beyoncé settles on crazy, then returns to anger. "You let this good love get to waste." —O'Shaughnessy

22. "Cry Me a River," Justin Timberlake

Most breaking lyric: "You lot didn't know all the ways I loved yous, no / And then you took a chance / And fabricated other plans"

Entering 2002, Justin Timberlake wasn't regarded equally much more a teeny bopper. His grouping 'NSync was 1 of the defining groups of the boy band era, and he was its charismatic face. (The cute one, if you will.) He fifty-fifty had the perfect girlfriend for that blazon of stardom: Britney Spears, with whom he pulled off this iconic denim fit. Then the couple broke up, JT split from 'NSync, and "Cry Me a River" happened.

In his first solo megahit, Justin insinuates his dearest 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 adept. He's already cried about it, and now it'due south her turn. But no corporeality of her tears tin can undo the impairment; he's gone. You didn't have to do much sleuthing to figure out he was singing nigh Britney. That celebrity intrigue, Timbaland's sharp production, and an instantly memorable music video combined to make "Cry Me a River" the most iconic breakdown song of the early 2000s, catapulting him to another level of distinction. He had split with not only Britney, only also his past, and he was ready for the world. —Sayles

21. "With or Without You," U2

Near heartbreaking line: "She got me with nothing to win / And goose egg left to lose"

Cipher changes if nothing changes, as they say, and "With or Without You" exists in that hopelessly recursive "I hate that I dearest you" space. This song was U2'south first no. 1 hit in the U.S., fifty-fifty though, Bono has said, "information technology's a very odd-sounding song … it kind of whispers its way into the world." But it's not the whispers that resonate nearly, however, it's all those wails, like the crescendo of Bono'due south aching, eminently singalong-able ahhh-ahhh-ahh-ahhhhhs, or the painful, everlasting notes from the Edge'southward "infinite guitar," engineered to hold a tone as if it were a grudge. "Psychotic restraint" is how Bono characterized the Border's spare work on this rail, a description that could double as breakup communication. —Katie Baker

xx. "Jolene," Dolly Parton

Almost heartbreaking line: "And I can easily understand / How you could hands 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 cute redhead past, say, digging a key into the side of his pretty little souped-upwardly 4-bike bulldoze, or—only spitballing here—threatening to transport her to Fist City, Parton simply pleads for mercy. The desperate pitch of her appeal, set confronting a frantic Dorian-mode guitar riff, sets the stakes far higher than those you might discover in more often than not stern state songs about cheatin', lyin', and existence untrue. Any armchair scholar of Parton's work can tell you lot she cloaks feminist manifestos within marketable diddies about everyday experiences. I've e'er taken the song's urgency to imply something that every woman learns somewhen: Relationships tin be both romantically fulfilling, and, too often, an economic lifeboat to a better life. In "Jolene," our narrator isn't only grasping onto her man, she'due south grasping for survival. —Alyssa Bereznak

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

Most heartbreaking line: "Practice you programme to let me go / For the other guy you loved before?"

This song was commencement released by Gladys Knight and the Pips in 1967. A twelvemonth afterward 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-old adult female when he was only 24, and their wedlock was full of infidelities. "I was in dear with the idea of beloved," 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 you?"

"Ex-Gene" is more than a breakup song, it's about recognizing a toxic relationship earlier yous take the words to call it a toxic relationship. Each line, then honest information technology hurts, is most the fruitless search for reason in a scenario devoid of information technology. Colina'southward lyrics capture the worst of the worst of a relationship on the rocks: the hurting, the complicity, and the unwillingness to give upwardly on a love you lot think is all the same there, buried below the bullshit.

When it striking airwaves again in 2018 on Drake'south pandering still irresistible "Nice for What," information technology was virtually like recognizing and reclaiming a past cocky—i who might have cried along to the original. At present, equally wiser, more Empowered™ listeners, we heard the remixed, catchy hook devoid of its devastating verses and bopped our heads equally Drake reminded us of how short life is. Still, no one can capture the raw, uncomfortable emotion that Lauryn originally did—and no 1 ever will. —Johnson

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

Well-nigh heartbreaking line: "Well, you said that we made such a pretty pair / And that you would never leave / Merely you gave away the things you loved / And ane of them was me"

Far before Taylor Swift sent her fans on subtweet scavenger hunts, Carly Simon penned a epic kissoff that, thanks to its self-referential chorus, left the globe wondering whom it was about and what they could've mayhap done to anger her. More than twoscore years of speculation subsequently, we now know that the singer was describing the histrion Warren Beatty. (She added in a recent, withering interview that, although the song describes iii separate men, Beatty "thinks the whole matter is about him.") Nosotros may never know what visitor he kept (cough: Mick Jagger?), but the lasting ability of Simon's clear-eyed takedown stands every bit 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

Most heartbreaking line: "Yes, I know information technology's stupid, I but gotta see information technology for myself"

Last year, post-obit a Robyn show at Madison Square Garden, elated concertgoers connected the party on the A/C/East railroad train subway platform, breaking into a dizzy public operation of "Dancing on My Own." You wouldn't typically look a breakdown song to exist the one that leads New Yorkers to such displays of collective joy, but most breakup songs aren't like this one: a song you tin can strut to, a club anthem, a scene-stealer, a story of lonesomeness that even so finds its solace in a crowd. Information technology'due south a song almost moving on—I just came to say cheerio—just as well nigh, merely, moving. The singer might be alone in the corner, and she might know it'south stupid, merely she's out there dancing, at least. —Bakery

xv. "Thank U, Next," Ariana Grande

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

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

This to do the actual, day-in, solar day-out work of existence happy. —Peters

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

Most heartbreaking line: "It's unnatural"

Both the joyous genesis and apple-polishing death knell for billions of '90s junior-high-gymnasium-dance relationships that but lasted the length of the song itself, "End of the Road," which rose to power on 1992's Boomerang soundtrack, is one of the biggest hits in pop-music history. Like, "13 directly weeks atop the Hot 100" big. Similar, "The 'One-time Town Road' of Its Twenty-four hours" large, a tearjerking shout-along anthem for lovelorn belters too 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: "It'due south unnatural / You vest to me / I belong to y'all." The word unnatural has never sounded and then natural, and so miserable. —Harvilla

thirteen. "Dreams," Fleetwood Mac

Most heartbreaking line: "Now here yous become again, you say you want your freedom / Well, who am I to continue you down?"

Even 40-plus years on, to hear Stevie Nicks softly moaning, "What you had ... and what you lost / And what yous had ... and what y'all 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 form, has been known to chugalug out a sweetly caustic breakup anthem or two himself.) As the second (and best!) track on 1977's zillions-selling Rumours, "Dreams" is both radically overexposed and still somehow criminally underrated, fixed to its iconic place, fourth dimension, and circumstances but also shockingly timeless. (Zoë Kravitz rhapsodizes it in the pilot of Hulu's new Loftier Fidelity remake serial to prove her rock-nerd bona fides.) Pair information technology with "Argent Springs" for maximum effect. —Harvilla

12. "How Can You lot Mend a Broken Eye," Al Green

Most heartbreaking line: "Let me alive again"

There'southward heartbreak, and then in that location's Al Dark-green heartbreak. (Not to slight the original Bee Gees version—Light-green is all I know when I'm going through it.) He'due south exasperated from the outset, wondering whether he'll ever recover from the dearest that went away. The agony is enough to contemplate nature itself in the chorus: "How can you lot mend a broken center? / How tin can you finish the rain from falling down? / How tin you end the lord's day from shining? / What makes the world go round?" Greenish is begging for answers, for "somebody, please" to come fix him. He pleads, "Let me alive again." Life as he knew it is over without this person, and equally long every bit the song is on, it feels over for the states, likewise. —O'Shaughnessy

xi. "Torn," Natalie Imbruglia

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

In that location's a bad breakup, there'due south rock bottom, and so there'southward being "cold and shamed, lying naked on the floor." Natalie Imbruglia's 1997 one-hit wonder (and sneaky cover) doesn't mince words in describing exactly how shitty it feels to put your religion in the wrong human being. (Or any human, depending on how hard y'all vibe with this vocal.) "Torn" has taken a turn for the over-covered and over-memed these days, just you're lying if y'all say you lot don't however hit that chorus every time. —Halliwell

10. "I Will Survive," Gloria Gaynor

Most heartbreaking line: "And and then you felt like dropping in and merely expect me to exist free / Well now I'thousand saving all my lovin' for someone who's lovin' me"

This 1978 disco colossus is so singular, so monolithic, so wedding-dancefloor-ingrained that it hardly scans as a breakup song at all: As ecstatic and empowering fuck-y'all anthems become, it is the glamorous grandmother to Lizzo's "Truth Hurts" and Ariana Grande's "Give thanks U, Side by side" and Beyoncé's "Irreplaceable" and roughly l,000 other self-affirming pop hits. What truly elevates New Jersey diva Gloria Gaynor'south 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 relate in whatsoever way, frivolously or otherwise, to the bluntly iconic line "I'k saving all my lovin' for someone who'southward lovin' me," which of course is everybody. She knows you're afraid; she knows you're petrified. Merely she also knows yous won't stay that way for long. —Harvilla

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

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

To make a vocal from 1971 virtually a video game from 2010: Dante'south Inferno is an RPG based loosely on the kickoff canticle 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 nighttime, who've stolen his beloved Beatrice. I never played information technology, but a friend who did described his frustration with the game: Information technology's every bit if its conclusion got further abroad the more time he devoted to it. A Super Bowl commercial showed Dante sprinting toward Hell'due south gaping mouth determined only, you know, definitely doomed. Every bit he descends you hear the low croak of Neb Withers'south vocalism, pining after a lost lover: "Ain't no sunshine when she's gone, simply 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 Similar You lot," Adele

Most heartbreaking line: "Sometimes information technology lasts in love, but sometimes it hurts instead"

The queen of heartbreak has never been meliorate than on sophomore album 21, and 21 doesn't get much better than "Someone Similar You." Adele'south ode to the one who got away is perhaps 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 course, that voice! Watching the unproblematic black and white music video now, it'due south hit how babe-faced Adele was at 21, despite her delivery of a song that displays so much emotional maturity. She wishes the all-time for her ex ("Old friend, why are you so shy?"), just damn, she'south nonetheless pain. Aren't we all! —Halliwell

7. "I Want You Back," The Jackson 5

Nigh heartbreaking lyrics: "Someone picked you lot from the bunch, one glance was all information technology took / At present it'due south much too tardily for me to have a second expect"

Maybe the most outwardly joyous vocal in this entire ranking, "I Want You lot Back" spins a tale that anyone who'southward always taken someone for granted will empathise. An eleven-year-sometime Michael Jackson is at his most precocious here, singing about the girl whom he didn't fully appreciate until someone else stole her heart. At present he just wants another chance to testify that he knows how to care for her right. Michael, of form, didn't write the song—it was penned by Berry Gordy and Co.—simply he sells it in a way that someone two or three times his age never could. A leopard can't change its spots, but if it sounds this expert trying to convince yous it can, why not requite it one more chance? —Sayles

six. "Since U Been Gone," Kelly Clarkson

Most heartbreaking line: "How come I'd never hear yous say / 'I just wanna be with you' (be with you lot) / I guess you never felt that style"

At that place is a moment in every breakup where, afterwards a few weeks of self-pity, you lot shed your sweatpant cocoon, step outside, and, with the instantaneity of a rubber band snap, suddenly know deep inside your middle that your ex was an insufferable blowhard. Kelly Clarkson's mosh-adjacent power popular ballad embodies the newfound cocky-assurance that comes with that realization. Information technology besides happens to be enshrined in a pop culture moment that I will forever associate with being a melodramatic xvi-year-old millennial: "Since U Been Gone" was written past popular lords Max Martin and Dr. Luke, who ripped its entire musical construction from the far more than poetic Yeah Yeah Yeahs hit, "Maps," and so—after being passed up by both Pink and Hilary Duff—was sung by the very offset winner of the so-fledgling reality Goggle box bear witness American Idol. The AIM-friendly "U" in the championship is but the icing on the cake. —Bereznak

5. "Ms. Jackson," Outkast

Nigh heartbreaking lyric: "Forever never seems that long until y'all're grown / And notice that the day-by-day ruler tin can't be too wrong"

Sometimes breaking up with your significant other's family is just 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 verse is especially poignant—his intentions were adept, simply things took a turn for the worse. It's a harsh reality: Nigh relationships are born with an expiration appointment, no matter how bright the flame burned at the commencement. Every bit far as apology songs get, it'south 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

iv. "I Will Always Dear You," Whitney Houston

Virtually heartbreaking line: "Please don't cry / We both know I'm not what you lot, yous demand"

Dolly Parton wrote 1 of the well-nigh dynamic love songs ever with "I Will Always Dear Yous." Whitney Houston, who sang a encompass for the pic The Bodyguard, made a worldwide hit with her phenomenal range. Both versions are wonderful for different reasons, though Parton's honeyed, wobbly original is best for heartbreak. For one, information technology's authentic: She wrote the song for her former manager and professional person partner, Porter Wagoner, later she decided to leave him. Parton is sympathetic, yet determined to go. As she sings in the bridge, it'southward bittersweet. They are both improve off this way, she argues, but wishes him zero simply "joy and happiness." I of the hardest relationship lessons is that 2 people can beloved each other and it still not be right for either—thanks to Dolly and Whitney, it was one learned early. —O'Shaughnessy

three. "I Can't Make Yous Love Me," Bonnie Raitt

Nigh heartbreaking line: "I'll close my eyes / And then I won't see / The love you lot don't feel when you're holding me"

You might be a girlfriend, a husband, a partner, or even a friend with benefits. Whatever role you play in service of dear, it comes with a characterization that sets expectations. There is clarity and condolement in knowing where you stand with someone. Only despite all of our semantics and promises, the terrifying reality of our love lives is that dear itself tin can exist a ruthlessly nonbinding agreement, an at-volition organization. Even more frightening is that information technology's oft our hearts—not us—calling the shots.

What sets "I Can't Brand You Dearest Me" apart from most breakup songs is that it takes place at the nigh painful point of a breakup: acceptance. Information technology's not a post-breakdown canticle of empowerment or a desperate plea to stay together. It's the full force of the disorienting one-2 punch of loss and loneliness. It'south the world-shattering moment when you give up the fight.

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

The songs that touch us virtually deeply are the ones that unite u.s.a. through the nearly human being of shared experiences. Somewhen, we all learn that y'all can't make someone's middle feel "something it won't." But should y'all one day observe yourself at rock lesser, suddenly lone in darkness—whether it's your first time or your 14th—y'all can feel a little flake less lonely knowing that Bonnie's been at that place, too. —James

2. "You Oughta Know," Alanis Morissette

About heartbreaking line: "Does she know how you lot told me y'all'd hold me until you died, till you died / Simply yous're all the same alive"

Alanis Morrisette was 19 years former when she recorded that carol of bitterness "You Oughta Know" in i take at 11 p.g. "All those vocals are just her at the end of the nighttime," said her cowriter Glen Ballard in an oral history of the album Jagged Petty Pill, "singing something she only wrote." The issue 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 perchance inspired by Uncle Joey remains both iconic and deeply weird, but besides makes sick sense: Y'all haven't truly been jilted until y'all've been jilted by someone who's not fifty-fifty 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 sweet, sweetness vengeance? —Baker

1. "Purple Rain," Prince

Most heartbreaking line: "I never meant to crusade you any 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 result of blood mixing with the heaven, which is a sort of apocalyptic drama that only Prince could conjure. Merely you don't even need to understand what purple rain is to feel "Purple Rain," a ability ballad to end all power ballads.

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

evansmookedis.blogspot.com

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