The 50 Greatest Breakup Songs of All Time

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In honor of Valentine’s Day, The Ringer presents an inventory of probably the most iconic tearjerkers and empowerment anthems in music historical past

What makes a track a “breakup track”? Does it need to be empowering, à la “I Will Survive” or a lot of the songs on Lemonade? Should it's for the lonely, like Carole King’s “It’s Too Late” or Bob Dylan’s “If You See Her, Say Hiya”? Does it have to deal with the breakup within the lyrics? (Taylor Swift has many entrants on this class, and Marvin Gaye penned an entire album about his divorce.) What about songs with a famous backstory, like “Cry Me a River” or any monitor off of Rumours?

We right here at The Ringer consider that since heartache comes in many varieties, so ought to the breakup track. And in honor of Valentine’s Day, we decided to dig deep into the style. Under, you’ll find our rating of the 50 biggest breakup songs of all time, as voted on by our employees. The listing spans a number of many years and many various moods, however all are rooted in some sort of pain. There was only one rule for the final rating: only one music per artist was included to avoid Dolly Parton or even Drake from dominating.

So in case you’re lonely, hearth up our playlist and cry alongside as you learn our ideas on every entrant. In case you’re happily hooked up, you possibly can nonetheless dive in—these are a few of the biggest songs ever recorded, and that’s true whether you’re in your emotions or not. Perhaps you’ll achieve a higher appreciation in your current relationship. In any case, breakup songs resonate only when you understand what it’s wish to lose in love. —Justin Sayles


50. “We Are Never Ever Getting Back Together,” Taylor Swift

Most heartbreaking line: “You'd disguise away and discover your peace of thoughts / With some indie report that’s so much cooler than mine”

Some of the savage breakup songs in historical past, “We Are By no means Ever Getting Back Together” encapsulates the extreme “fuck that man!” power that follows a long-overdue parting of the way. We’ve all had that post-fight rant with our pals: “Ugh … so he calls me up and he’s like, ‘I still love you,’ and I’m like … ‘I simply … I mean this is exhausting, you recognize, like, we're never getting back collectively. Like, ever.’” Flippant, triumphant, and completely exhausted by All Men, Taylor Swift gave us the right soundtrack for breakup restoration. Kate Halliwell

49. “I Miss You,” Blink-182

Most heartbreaking line: “I want any person and all the time / This sick strange darkness / Comes creeping on so haunting every time”

“I Miss You” is like a minimalist/emo take on Meat Loaf. It guidelines. The 2 greatest things about this quantity are Travis Barker’s simple but persistent drumbeat and Tom DeLonge’s entrance on the second verse. It’s a part of the grand pop punk tradition of displaying you mean business by going up an octave, of which “I Miss You” (together with the Beginning Line’s “The Best of Me”) is the exemplar.

Don’t simply take my phrase for it, although. Contemplate Grammy-winning producer Finneas’s take: “Tom comes into that music like he was on a balcony and he jumped off the balcony onto the track.” —Michael Baumann

48. “It’s Too Late,” Carole King

Most heartbreaking line: “But we simply can’t keep collectively, don’t you are feeling it, too? / Still I’m glad for what we had and how I once beloved you”

“It’s Too Late” is a crushing ode to the most typical sort of breakup. The natural means of two individuals growing apart is as heartbreaking as it is commonplace, and King sings in a tone completely located between her sorrow and the shrugging admission that “we actually did attempt to make it.” Her conversational delivery early in the track brings us into the lounge, diner, or sidewalk the place “the speak” between her and her about-to-be-ex is occurring: “Certainly one of us is changing, or perhaps we simply stopped making an attempt,” she sings, plainly laying out the central, blameless causes for why most individuals find yourself separating. The track is outlined by its maturity and its conciliatory angle, but as with precise breakup conversations, that doesn’t make it any easier to listen to. —Cory McConnell

47. “Un-Break My Heart,” Toni Braxton

Most heartbreaking line: “I can’t overlook the day you left / Time is so unkind”

This can be a good example of the type of breakup track you hear on the radio (or, in the late ’90s, probably the membership—the Frankie Knuckles house remix nonetheless goes) and, on a traditional day, simply hear another pop music, however once you’re experiencing heartache, what initially seemed like songwriting clichés turn into the truest words you’ve ever heard. “I have cried a variety of nights,” you assume, getting away from bed for the primary time in days to grab a roll of toilet paper since you ran out of Kleenex. “Life is merciless with out you here beside me,” you murmur, staring into the awful chasm of loneliness you now know as life. “I might actually do something on God’s green earth to listen to you say you're keen on me once more,” you understand with the greatest readability you’ve ever experienced. Anyway, where are my altos at? This is our karaoke music. Kjerstin Johnson

46. “Mr. Brightside,” the Killers

Most heartbreaking line: “Now they’re going to bed and my stomach is sick / And it’s all in my head”

Perhaps it’s not exactly right to call “Mr. Brightside” a breakup track; perhaps it’s extra correct to name it a right-before-the-breakup track, an I-imagined-my-girlfriend-was-cheating-on-me-so-intensely-that-she-actually-started-cheating-on-me track. But that’s all actually clunky, so let’s accept being barely incorrect for the sake of cleanliness. Either method, “Mr. Brightside” is an iconic mid-aughts track that’s good for yell-karaoking and that pulls off the troublesome trick of just repeating one verse time and again. Also, Eric Roberts within the video. —Andrew Gruttadaro

45. “She’s Gone,” Hall & Oates

Most heartbreaking line: “Rise up within the morning, look in the mirror / One less toothbrush hanging within the stand”

The dynamic duo of Daryl Corridor and John Oates turned feather-haired, MTV-borne superstars within the ’80s, however their rise to greatness begins here, with the breakout hit from their second album, 1973’s oddly/heartbreakingly named Abandoned Luncheonette. “She’s Gone” is luscious and silky and deceptively mild, all Motown grandeur by means of blue-eyed Philly soul, but that lightness only underscores the beautiful heaviness of murmured verse strains like “Rise up within the morning, look within the mirror / Worn as the toothbrush hanging within the stand.” (Or in all probability it’s “One much less toothbrush,” which in fact is even heavier.) The refrain, against this, is gigantic and majestic and crushing, punctuated by cloudbursting lamentations of “She’s gone! / Oh why? / Oh why?” The boys solely acquired greater from right here, however they definitely by no means obtained sadder. —Rob Harvilla

44. “Tyrone,” Erykah Badu

Most heartbreaking line: “I simply want it to be, you and me, prefer it was, child / But ya don’t know how one can act”

The second-best moment on this viciously sultry sluggish jam, the crown jewel of Erykah Badu’s 1997 album Reside, is the stupendous opening line: “I’m gettin’ uninterested in your shit / You don’t ever buy me nothin’.” The primary-best moment is all the women within the crowd immediately shrieking with delight and, one fears, recognition. “Tyrone” is known as for certainly one of an unnamed deadbeat lover’s numerous deadbeat buddies: “Each time we go someplace,” Badu purrs with lethal authority, “I gotta attain down in my purse / To pay your method and your homeboy’s approach and typically your cousin’s method.” It's the gender-flipped riposte to Friday’s “Bye, Felicia,” and actually turned up as a joke in 2000’s Next Friday; it “followed me through my profession like an obsessed X boyfriend,” as Badu put it on Instagram in 2017, whereas shouting out her backup singers, whose sardonic and stylish “Call him!” chant is the third-best moment. —Harvilla

43. “Love Is a Battlefield,” Pat Benatar

Most heartbreaking line: “Do I stand in your means / Or am I the perfect thing you’ve had?”

The agonizingly propulsive signature hit from flamethrower-voiced ’80s pop queen Pat Benatar laments not so much a breakup as a near-breakup in progress, an acknowledgement that real love means virtually breaking up just about on a regular basis: “Consider me / Consider me / I can’t inform you why / But I’m trapped by your love / And I’m chained to your aspect.” It’s a karaoke basic you haven't any enterprise trying, a cheeseball Reagan-era smash of everlasting profundity, and a hanging declaration that typically the only factor worse than splitting up is not splitting up: “Do I stand in your method / Or am I one of the best factor you’ve had?” she wails with real desperation, and the reply, in fact, is both. —Harvilla

42. “Devil in a New Dress,” Kanye West

Most heartbreaking line: “Throwing shit around, the whole place screwed up / Perhaps I ought to call Mase so that he might pray for us”

We’re not even speaking about the whole music—we’re talking about 20 or so seconds of Bink production after Kanye’s second verse, however earlier than Rick Ross’s solely verse, arguably probably the greatest in his career. In it, he describes West’s near-fatal automotive crash in 2002 as an aborted climb “up the Lord’s ladder,” and truthfully, that’s precisely what the gathering of energy strings sound like on this bridge. A climb up the Lord’s ladder, a departure from Earth, a one-way journey to anyplace but here. —Micah Peters

41. “Suspicious Minds,” Elvis Presley

Most heartbreaking line: “We will’t go on collectively / With suspicious minds / And we will’t build our goals / On suspicious minds”

You'll be able to see the ripples of “Suspicious Minds” throughout the course of breakup track history, from “Practice in Vain” to “Dancing on My Own,” which, you already know, it’s Elvis. But beyond the juxtaposition of its relatively upbeat music and depressing-as-hell lyrics, I really like the structure of this track, with a peppy guitar intro and verses that build into a chorus that goes from G main to very, very E minor and simply doesn’t ever actually resolve. This won't be the one purpose the music fades out however there’s no actual appropriate ending level for the last notes of the chorus, so it all the time drops back into a verse or a bridge or one other refrain. “John Jacob Jingleheimer Schmidt” resolves extra easily. Identical to a damaged relationship. —Baumann

40. “The Tracks of My Tears,” Smokey Robinson & the Miracles

Most heartbreaking strains: “Though she may be cute, she’s just a substitute / Since you’re the everlasting one”

On this basic Motown tearjerker, Smokey embodies the thought of the sad clown better than any track ever has. He’s the life of the get together—utilizing jokes like a clown makes use of make-up—but inside, he’s wounded, pining for a previous lover. He’s courting someone new, but he’s not considering of her. (Aspect word: I don’t know who I’m sadder for here, Smokey or the rebound he’s strolling round city with.) He might have wiped away the tears, but they’ve left their mark. And the makeup solely makes the tear tracks that rather more obvious. —Justin Sayles

39. “Tears Dry on Their Own,” Amy Winehouse

Most heartbreaking line: “So that is inevitable withdrawal / Even if I cease wanting you / And perspective pushes by way of / I’ll be some subsequent man’s different lady quickly.”

On “Tears Dry on Their Own,” Amy Winehouse demanded that Amy Winehouse take her own advice. “I can't play myself again, I should simply be my very own greatest good friend,” she warns. “Not fuck myself within the head with stupid males.” These strains that pried the music open have been one in every of Winehouse’s hallmarks as a author—“Tears” begins within the dumps, within the aftermath. But during each emotional uncoupling comes the point the place you gaze into the mirror, stick your finger in your reflection’s chest, and inform them to stop being such a dumb, whiny baby. —Peters

38. “Needed Me,” Rihanna

Most heartbreaking strains: “Fuck your white horse and a carriage / Guess you by no means might imagine / By no means informed you you might have it / You wanted me”

This music is so petty and I love it. Rihanna principally made successful off the “Sike, you thought!” meme and DJ Mustard added an unforgettable beat behind it. That is a type of bangers that you simply and your women blast post-breakup, pre-going-out. Then, after you all sing in unison: “Don’t get it twisted / You was simply another nigga on the hit record / Tryna fix your inside points with a nasty bitch,” you all burst into laughter fascinated by the person who's now barely a reminiscence. Rihanna’s confidence and savageness is basically on an untouchable degree. (Keep in mind, this track is on the same album where she sings “intercourse with me is so superb time and again.) Lengthy might she reign. —Jordan Ligons

37. “So Sick,” Ne-Yo

Most heartbreaking line: “Gotta change my answering machine, now that I’m alone / ’Trigger proper now it says that we will’t come to the telephone”

The earworm of a era! Ne-Yo stated no to sappy ballads in more ways than one with “So Sick,” giving us an R&B smash hit for everyone sick of normal, schmegular love songs. Set to the world’s catchiest beat, Ne-Yo mourns a previous relationship and all the day-to-day modifications that include shifting on. “Gotta change my answering machine, now that I’m alone / ’Trigger right now it says that we will’t come to the telephone … Gotta fix that calendar I have that’s marked July 15 / Because since there’s no extra you, there’s no more anniversary.” Fifteen years later, we still can’t flip off the radio. —Halliwell

36. “We Belong Together,” Mariah Carey

Most heartbreaking line: “Once you left I misplaced part of me / It’s still so exhausting to consider / Come back baby, please / ‘Cause we belong collectively”

*Sighs.* That is simply probably the most played-out, sad breakup music of the early 2000s. Everyone considered someone who might’ve/should’ve been their soul mate when this dropped in 2005. However now if it comes on the radio and also you’re both fortunately single or in a strong relationship, your eyes will glaze over, guaranteed. When the primary two seconds of the notorious beat come via my speakers, I’m already altering the station. It’s simply so annoying, and so Mariah.

Chances are you'll assume that you simply gained’t find someone else to lean on when occasions get rough or someone to talk to you on the telephone until the sun comes up, but let me inform you, you'll and you’ll be high quality. Breakups suck, however please don’t torture your broken heart (or your ears) by listening to this music on repeat. —Ligons

35. “If You See Her, Say Hello,” Bob Dylan

Most heartbreaking line: “Say for me that I’m all right, although things get type of sluggish / She may assume that I’ve forgotten her, don’t inform her it isn’t so.”

The inspiration for Bob Dylan’s masterful Blood on the Tracks has all the time been debated. Critics have lengthy assumed that the album is about Dylan’s separation from his spouse, Sara. The couple’s son, Jakob, reportedly believes that Blood is about his parents. However Dylan himself has steadily denied that his masterpiece is autobiographical, even saying as an alternative that it’s based mostly on … Chekhov’s short stories. “I don’t write confessional songs,” Dylan told Cameron Crowe in the course of the release of the immersive (and, within the context of this quote, sarcastically named) Biograph. The reality is, it doesn’t matter. Blood strikes such a chord because the heartache it mines feels directly deeply personal and universal.

That’s most palpable on “If You See Her, Say Hey,” which brings us into a fractured relationship in a means that’s both effortlessly relatable (“We had a falling out, like lovers typically will”) and hyper-specific (“And to think about how she left that night time, it nonetheless brings me a chill”). It’s not Dylan’s flashiest or heaviest or greatest music, however it's my favourite, a mild, intimate portrait of misplaced love and lasting anguish. Like a lot of his greatest work, it’s propelled by its poetry, the uncooked insights about how it feels to be alive. The track cycles via the same phases that so many people do whereas processing heartbreak: denial, despair, anger, want. It floats on a current of regret (“Sundown, yellow moon, I replay the previous / I know each scene by coronary heart, they all went by so quick”) but manages to convey the sort of longing that leads, cautiously, back toward hope (“If she’s passing back this manner, I’m not that onerous to seek out / Tell her she will look me up, if she’s received the time”). After sufficient listens, and enough heartache of your personal, you understand that “If You See Her, Say Hey” isn’t really a breakup track. It’s a love letter. Mallory Rubin

34. “Don’t Look Back in Anger,” Oasis

Most heartbreaking line: “Rise up beside the fireside / Take that look from off your face / ’Trigger you ain’t ever gonna burn my coronary heart out”

The closest I’ve ever come to dwelling in an episode of Glee was when my high school French class spontaneously broke out singing “Don’t Look Back in Anger.” I don’t keep in mind why, however it cemented this music (at the least for me) as a ballad of communal weltschmerz, fairly than personal unhappiness or remorse, like a fin-de-siècle “You’ll By no means Stroll Alone.” (For example: “Don’t Look Back in Anger” turned a type of unofficial anthem after the Manchester bombing in 2017.) Oasis knows a factor or two about writing for the communal sing-along, the significance of the languid, memorable melody and the propulsive chord change—this track would carry about the same emotional weight if it have been only a title and a refrain. —Baumann

33. “Every Breath You Take,” the Police

Most heartbreaking line: “Since you’ve gone I’ve been lost with no hint / I dream at night time, I can solely see your face”

This spectacularly maudlin New Wave ballad, which anchored the Police’s 1983 goliath Synchronicity and reigned as one of the largest radio hits of the decade, is creepy as all hell, very much by design: an unrepentant stalker manifesto that doesn’t a lot describe spurned love when it comes to surveillance because it describes complete state surveillance when it comes to spurned love: “Each move you make / Each vow you break / Each smile you pretend / Every declare you stake.” And so forth. “I’ll be watching you,” Sting concludes a pair dozen occasions all through, nevertheless it’s the chest-pounding bridge where the trio’s creepy-soulful frontman does a few of his greatest belting, his greatest pleading, his greatest super-creepy emoting and enunciating: “I really feel so cold and I lengthy on your em-brace.” Fun reality: He started writing the track at Ian Fleming’s writing desk on the James Bond writer’s luxe Jamaican property, which might not be creepy, nevertheless it’s definitely weird. —Harvilla

32. “Don’t Speak,” No Doubt

Most heartbreaking line: “As we die, each you and I / With my head in my palms, I sit and cry”

I mean, truthfully, it takes a number of guts to drop a Spanish classical guitar solo in the midst of an angsty ’90s alt-rock music. It also takes numerous guts to put in writing a music about breaking apart with the bass player in your band after which make a music video for the music that has photographs in it just like the one under: Don’t converse, literally.

No Doubt’s first hit is a murals, filled with uncooked, youthful emotion and sophisticated arrangements. It’s lovely, brutal, painful, and incendiary, abruptly. —Gruttadaro

31. “Thinkin Bout You,” Frank Ocean

Most heartbreaking strains: “Do you not assume up to now ahead? / ‘Trigger I been thinkin’ bout ceaselessly”

Typically you need to misinform your self to get by means of heartache. They weren’t ok for me. I can do better. I didn’t love them, I just thought they have been cute. Frank Ocean’s “Thinkin Bout You” exposes that type of posturing for what it is: a facade. No, I wasn’t crying about you, and by the best way, I also own waterfront property in Idaho. Frank’s clearly still hung up on the previous even when his previous flame isn’t. And the only solution to work by way of the pain is to drop the lying and are available clean with himself. It’s tender, it’s candy, however most of all, it’s trustworthy. —Sayles

30. “I’m Goin’ Down,” Mary J. Blige

Most heartbreaking strains: “Why’d you need to say goodbye? / Look what you’ve executed to me / I can’t cease these tears from fallin’ from my eyes”

Regardless of your current relationship status, you'll for positive sing your heart out when this music comes on. I do not care, I am Mary J. when the chorus hits. By the top of the music—a canopy of Rose Royce’s 1976 single—you’ve “gone down” a lot that you simply’re on the ground, eyes closed, hoop earrings in, and belting, “My entire world’s up-[dramatic pause]-side down!” I can’t be the only one, right?

Also, keep in mind when Tamera sang this music for the talent show on Sister, Sister? Iconic. —Ligons

29. “Nothing Compares 2 U,” Sinéad O’Connor

Most heartbreaking strains: “I might put my arms round each boy I see / However they’d only remind me of you”

Breakups are liberating; breakups are imprisoning. If you come out of a yearslong relationship, you need to relearn tips on how to reside without that individual in your life. Elements of that course of are lovely—reconnecting with previous pals, choosing up a brand new interest, shaking off the shackles. However the breakup sticks with you. You run into your ex’s greatest good friend on the bar, otherwise you hear a track that you simply each beloved. Typically, it’s a minor annoyance. Other occasions, it’s an earth-shattering occasion. You’re relearning methods to reside, however dwelling is troublesome.

I can’t consider a music that higher captures that duality than “Nothing Compares 2 U,” the 1990 O’Connor hit initially penned by Prince in 1985. You can do no matter you want: You'll be able to get together all night time, you possibly can eat at a flowery restaurant, you possibly can put your arms round all of the girls and boys you’d like, however it doesn’t matter. It’s not them, and nothing shall be. Your greatest hope is simply giving in and dwelling for your self. —Sayles

28. “Marvin’s Room,” Drake

Most heartbreaking line: “The lady that I might attempt / Is proud of an excellent man”

Drake is at his greatest when he’s damaging because he masks the gaslighting with a softer unhappiness. “The lady that I might attempt / Is proud of a very good guy,” he sings. Is he pleased for her? The strains recommend that there’s a minimum of a chance. Drake pauses, then goes full Drizzy Deleterious: “However I’ve been drinkin’ a lot / That I’ma name her anyway.” He proceeds to inform her that the person she’s with isn’t ok to switch what that they had. It’s the basic overstep from an ex, but the longer he goes on, we understand it’s about his delight and conflicting feelings about his life decisions than her. Drake spirals, telling her he’s “had sex 4 occasions this week / I can explain,” that he’s sponsoring ladies, that he can’t cease partying and asking for bare footage. Precisely what your ex-girlfriend needs to hear, I’m positive. No less than there’s a voicemail interlude. —Haley O’Shaughnessy

27. “Just a Friend,” Biz Markie

Most heartbreaking line: “Oh, snap! Guess what I saw? / A fella tongue-kissin’ my woman in her mouth”

Seems this lady didn't have what Biz Markie needed. As he singsplains, he turned kitten smitten with a lady at one among his exhibits. You’d assume that this might have happened to him all the time, however it didn't. This was “the primary woman I ever talked to,” Biz told EW last year. “Every time I might call out to California, a dude would decide up and hand her the telephone. I’d be like, ‘Yo, what’s up [with him]?’ She’d say, ‘Oh, he’s just a pal. He’s no one.’” Not taking the hint, Biz flew out to California to surprise her every week earlier than planned. When he confirmed up, there was a guy “tongue-kissing my woman in her mouth.”

Biz. My Guy. Sit down. Let’s speak. First off, she was not your woman. You met her one time. Second, you did not catch her tongue-kissing a dude. You stalked her. Third, it was extremely apparent that this good friend was not simply her good friend. What Biz Markie needed was someone to take heed to his story and provides him trustworthy suggestions about his predicament. You understand, a good friend. —Danny Heifetz

26. “Burn,” Usher

Most heartbreaking line: “However you recognize, gotta let it go/ ’Cause the get together ain’t jumpin’ prefer it used to/ Although this may bruise you/ Let it burn”

I couldn’t imagine someone breaking apart with me with the lyrics to this music. Usher is everywhere. He says he loves me, but our relationship has to return to an finish; he says he’s hurting and he’s not joyful, but he’s breaking down and crying. Deep down he is aware of it’s greatest, however he hates the thought of me being with another person. Get your shit together, Usher!

Nonetheless, for all of its confusing back-and-forth, this can be a breakup basic. It preaches the ideology of forcing your self to let go even whenever you don’t know what you’re going to do without your boo. After a heartbreak, everybody has found themselves teetering the road of remorse and freedom. Usher’s “Burn” permits you to tap into that while concurrently yelling out, “It’s been fifty-eleven days, umpteen hours, and Imma be burnin’ till you come back!” —Ligons

25. “Piece of My Heart,” Massive Brother & the Holding Firm

Most heartbreaking line: “However every time I inform myself that I, properly I can’t stand the pain / However once you maintain me in your arms, I’ll sing it as soon as again”

When you’re ever at your wits’ end, tragically obsessed with somebody who treats you want shit, yow will discover some catharsis in the controlled chaos of Janis Joplin’s vocal performance on “Piece of My Coronary heart.” Go ahead and scream alongside. You gained’t sound nearly as good as Janis, but you’ll definitely really feel a hell of so much better afterwards.

As soon as your anger fades slightly, you possibly can change over to the unique recording of this music, launched a yr earlier in 1967 and sung by Erma Franklin (sure, that’s Aretha’s older sister). Or when you need some extra twang accompanying your despair, you'll be able to attempt the Faith Hill version. I also gained’t decide you if the only one that can ease your ache is Shaggy (or Beverley Knight, Melissa Etheridge, Steven Tyler, Kelly Clarkson, or considered one of countless different artists).

Written by Jerry Ragovoy and Bert Berns, “Piece of My Coronary heart” is among the most relatable and enduring songs about Some Fuckboi in the historical past of fuckbois. The call-and-response structure of the refrain builds those simmering resentments and releases them with a sharp, primal cry. Undoubtedly, there might be new variations of this track until the top of time⁠—as a result of it’s an absolute banger—but in addition as a result of … males. —Matt James

24. “Skinny Love,” Bon Iver

Most heartbreaking line: “And I informed you to be affected person / And I informed you to be fantastic”

An excellent rule for breakup songs is that there needs to be an element which you can yell alongside to, unencumbered by silly issues like constraint and self-awareness. The refrain of Bon Iver’s “Skinny Love” has an ideal one, especially for anyone who’s simply exited a relationship and feels compelled to heap all of the blame on the opposite social gathering.

You understand the story by now: In 2006, Justin Vernon broke up together with his girlfriend, packed up his automotive, and drove into the Wisconsin wilderness, rising solely after recording an album of weepy breakup songs. That origin tale has been repeated so typically that it’s develop into gentle mush, obscuring the actual fact: That For Emma, Ceaselessly In the past—and particularly “Skinny Love”—are profoundly reflective, intelligent, shifting documents concerning the breakdown of a relationship. —Gruttadaro

23. “Hold Up,” Beyoncé

Most heartbreaking line: “Can’t you see there’s no other man above you? / What a depraved solution to treat the woman that loves you”

It’s arduous to precise real harm over an uptempo beat and make the heartbreak convincing. But Beyoncé is plausible in “Maintain Up,” a painful accounting of the feelings that come after discovering that your companion has cheated. Lemonade was inspired by true events—i.e., it’s Beyoncé coming to terms with Jay-Z being untrue. Infidelity brings on a really specific sort of devastation: You’re mad; you’re miserable; you’re humiliated. You turn from one emotion to a different in a matter of minutes. She opens the track with confidence: No different lady may give what she will. “Maintain up, they don’t love you like I really like you.” In a breath, she’s much less positive of herself: “What’s worse, wanting jealous or crazy?” Beyoncé settles on crazy, then returns to anger. “You let this good love go to waste.” —O’Shaughnessy

22. “Cry Me a River,” Justin Timberlake

Most breaking lyric: “You didn’t know all the ways I beloved you, no / So you took a chance / And made other plans”

Getting into 2002, Justin Timberlake wasn’t considered rather more than a teeny bopper. His group ’NSync was one of many defining teams of the boy band period, and he was its charismatic face. (The cute one, if you'll.) He even had the right girlfriend for that sort of stardom: Britney Spears, with whom he pulled off this iconic denim fit. Then the couple broke up, JT cut up from ’NSync, and “Cry Me a River” happened.

In his first solo megahit, Justin insinuates his love has cheated on him (“You don’t should say what you did / I already know, I came upon from him”) and writes her off for good. He’s already cried about it, and now it’s her flip. But no quantity of her tears can undo the injury; he’s gone. You didn’t need to do a lot sleuthing to determine he was singing about Britney. That superstar intrigue, Timbaland’s sharp production, and an instantly memorable music video combined to make “Cry Me a River” probably the most iconic breakup track of the early 2000s, catapulting him to another degree of stardom. He had cut up with not solely Britney, but in addition his past, and he was ready for the world. —Sayles

21. “With or Without You,” U2

Most heartbreaking line: “She obtained me with nothing to win / And nothing left to lose”

Nothing modifications if nothing modifications, as they say, and “With or With out You” exists in that hopelessly recursive “I hate that I really like you” area. This music was U2’s first no. 1 hit within the U.S., regardless that, Bono has said, “it’s a really odd-sounding track … it type of whispers its method into the world.” However it’s not the whispers that resonate most, nevertheless, it’s all these wails, like the crescendo of Bono’s aching, eminently singalong-able ahhh-ahhh-ahh-ahhhhhs, or the painful, eternal notes from the Edge’s “infinite guitar,” engineered to hold a tone as if it have been a grudge. “Psychotic restraint” is how Bono characterized the Edge’s spare work on this monitor, a description that would double as breakup recommendation. —Katie Baker

20. “Jolene,” Dolly Parton

Most heartbreaking line: “And I can easily understand / How you can easily take my man / But you don’t know what he means to me, Jolene”

Whereas other feminine country singers may’ve handled their man’s newfound fascination with a wonderful redhead by, say, digging a key into the aspect of his pretty little souped-up four-wheel drive, or—just spitballing right here—threatening to ship her to Fist City, Parton merely pleads for mercy. The desperate pitch of her attraction, set towards a frantic Dorian-mode guitar riff, units the stakes far greater than these you may find in usually stern nation songs about cheatin’, lyin’, and being untrue. Any armchair scholar of Parton’s work can inform you she cloaks feminist manifestos inside marketable diddies about on a regular basis experiences. I’ve all the time taken the music’s urgency to suggest one thing that each lady learns ultimately: Relationships might be both romantically fulfilling, and, too typically, an economic lifeboat to a greater life. In “Jolene,” our narrator isn’t just grasping onto her man, she’s grasping for survival. —Alyssa Bereznak

19. “I Heard It Through the Grapevine,” Marvin Gaye

Most heartbreaking line: “Do you propose to let me go / For the opposite guy you liked before?”

This track was first released by Gladys Knight and the Pips in 1967. A yr later Marvin Gaye released a slower version of it on his album In the Groove. Perhaps the track resonated with Gaye as a result of he married a 41-year-old lady when he was solely 24, and their marriage was filled with infidelities. “I was in love with the thought of love,” Gaye as soon as stated. Or at the very least that’s what I heard by way of the grapevine. —Heifetz

18. “Ex-Factor,” Lauryn Hill

Most heartbreaking line: “The place have been you once I wanted you?”

“Ex-Issue” is more than a breakup music, it’s about recognizing a poisonous relationship earlier than you have got the phrases to name it a poisonous relationship. Each line, so trustworthy it hurts, is concerning the fruitless seek for cause in a state of affairs devoid of it. Hill’s lyrics seize the worst of the worst of a relationship on the rocks: the ache, the complicity, and the unwillingness to give up on a love you assume continues to be there, buried beneath the bullshit.

When it hit airwaves again in 2018 on Drake’s pandering yet irresistibleNice for What,” it was virtually like recognizing and reclaiming a past self—one who may need cried along to the unique. Now, as wiser, extra Empowered™ listeners, we heard the remixed, catchy hook devoid of its devastating verses and bopped our heads as Drake reminded us of how brief life is. Nonetheless, nobody can capture the raw, uncomfortable emotion that Lauryn originally did—and no one ever will. —Johnson

17. “You’re So Vain,” Carly Simon

Most heartbreaking line: “Properly, you stated that we made such a reasonably pair / And that you would never depart/ However you gave away the belongings you liked / And one among them was me”

Far before Taylor Swift sent her followers on subtweet scavenger hunts, Carly Simon penned a ballsy kissoff that, because of its self-referential refrain, left the world wondering whom it was about and what they might’ve probably completed to anger her. Greater than 40 years of hypothesis later, we now know that the singer was describing the actor Warren Beatty. (She added in a current, withering interview that, although the track describes three separate men, Beatty “thinks the entire thing is about him.”) We might by no means know what firm he stored (cough: Mick Jagger?), but the lasting power of Simon’s clear-eyed takedown stands as a referendum on the unchecked male ego, whether its contained in the body of a dashing actor or a moody fuckboy. —Bereznak

16. “Dancing on My Own,” Robyn

Most heartbreaking line: “Yeah, I do know it’s stupid, I just gotta see it for myself”

Last yr, following a Robyn present at Madison Square Garden, elated concertgoers continued the celebration on the A/C/E practice subway platform, breaking right into a giddy public performance of “Dancing on My Personal.” You wouldn’t sometimes anticipate a breakup music to be the one which leads New Yorkers to such shows of collective joy, however most breakup songs aren’t like this one: a music you'll be able to strut to, a club anthem, a scene-stealer, a story of lonesomeness that also finds its solace in a crowd. It’s a music about shifting on—I just got here to say goodbye—but in addition about, simply, shifting. The singer may be alone in the corner, and she or he may comprehend it’s silly, however she’s on the market dancing, no less than. —Baker

15. “Thank U, Next,” Ariana Grande

Most heartbreaking line: “Wish I might say, ‘Thank you’ to Malcolm / ‘Cause he was an angel”

This track is a choice to be completed with suffering over a relationship, to recommit to oneself, to concentrate on healing and establishing new patterns. To not solely rehearse past losses however to ascer