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What makes a song a "breakup vocal"? Does it take to be empowering, à la "I Will Survive" or virtually of the songs on Lemonade? Should it be for the lonely, like Carole Rex's "Information technology'due south Too Late" or Bob Dylan's "If You See Her, Say Hullo"? Does information technology have to address the breakup in the lyrics? (Taylor Swift has many entrants in this category, and Marvin Gaye penned an unabridged anthology about his divorce.) What almost songs with a famous backstory, like "Cry Me a River" or whatever track off of Rumours?

We here at The Ringer believe that since heartache comes in many forms, so should the breakup vocal. And in laurels of Valentine's Twenty-four hours, we decided to dig deep into the genre. Below, you'll find our ranking of the 50 greatest breakdown songs of all time, as voted on by our staff. The list spans several decades and many dissimilar moods, but all are rooted in some type of hurting. In that location was just one dominion for the terminal ranking: just one vocal per artist was included to avoid Dolly Parton or even Drake from dominating.

So if you're lonely, fire up our playlist and cry along equally you read our thoughts on each entrant. If you lot're happily attached, you can still swoop in—these are some of the greatest songs ever recorded, and that's true whether you're in your feelings or not. Maybe y'all'll gain a greater appreciation for your electric current relationship. Later all, breakup songs resonate but when you know what it's like to lose in honey. —Justin Sayles

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

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

1 of the most savage breakup songs in history, "Nosotros Are Never Always Getting Back Together" encapsulates the severe "fuck that guy!" free energy that follows a long-overdue departing of ways. Nosotros've all had that post-fight rant with our friends: "Ugh … and so he calls me up and he'south like, 'I however honey y'all,' and I'1000 like … 'I just … I mean this is exhausting, you know, like, we are never getting back together. Like, e'er.'" Flippant, triumphant, and entirely exhausted by All Men, Taylor Swift gave us the perfect soundtrack for breakup recovery. — Kate Halliwell

49. "I Miss You," Blink-182

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

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

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

48. "Information technology'south Too Late," Carole King

Most heartbreaking line: "Just we but can't stay together, don't you feel it, also? / Still I'thousand glad for what we had and how I once loved yous"

"Information technology's Too Late" is a burdensome ode to the nigh common kind of breakup. The natural process of 2 people growing apart is as heartbreaking as it is commonplace, and Rex sings in a tone perfectly situated between her sorrow and the shrugging admission that "we really did try to make it." Her conversational delivery early on in the vocal brings us into the living room, diner, or sidewalk where "the talk" between her and her virtually-to-be-ex is happening: "One of u.s.a. is changing, or maybe nosotros simply stopped trying," she sings, plainly laying out the central, clean-living reasons for why most people end upwards separating. The vocal is defined by its maturity and its conciliatory mental attitude, but as with actual breakup conversations, that doesn't make it whatever easier to hear. —Cory McConnell

47. "Un-Break My Heart," Toni Braxton

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

This is a perfect example of the kind of breakup song you lot hear on the radio (or, in the late '90s, perchance the club—the Frankie Knuckles business firm remix still goes) and, on a normal day, just hear another pop song, but when you're experiencing heartache, what originally sounded similar songwriting clichés become the truest words yous've e'er heard. "I have 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 ran out of Kleenex. "Life is cruel without you hither beside me," yous murmur, staring into the bleak chasm of loneliness you lot at present know every bit life. "I would literally do anything on God's greenish earth to hear you say you dearest me once again," you realize with the greatest clarity you've always experienced. Anyway, where are my altos at? This is our karaoke song. — Kjerstin Johnson

46. "Mr. Brightside," the Killers

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

Perchance it's not exactly correct to call "Mr. Brightside" a breakdown song; maybe it's more accurate to phone call it a right-before-the-breakup song, an I-imagined-my-girlfriend-was-cheating-on-me-so-intensely-that-she-really-started-adulterous-on-me vocal. Just that'southward all actually clunky, and so let'south accept existence slightly wrong for the sake of cleanliness. Either manner, "Mr. Brightside" is an iconic mid-aughts song that's perfect for yell-karaoking and that pulls off the difficult fox of only repeating i verse over and over. Also, Eric Roberts in the video. —Andrew Gruttadaro

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

Well-nigh heartbreaking line: "Get up in the morning, wait 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, simply their rise to greatness begins hither, with the breakout hitting from their second album, 1973's oddly/heartbreakingly named Abandoned Luncheonette. "She's Gone" is luscious and silky and deceptively light, all Motown grandeur by way of blue-eyed Philly soul, but that lightness just underscores the exquisite heaviness of murmured verse lines similar "Go up in the morning, wait in the mirror / Worn as the toothbrush hanging in the stand." (Or probably it'south "One less toothbrush," which of form is even heavier.) The chorus, by contrast, is gigantic and purple and crushing, punctuated by cloudbursting lamentations of "She's gone! / Oh why? / Oh why?" The boys only got bigger from hither, simply they certainly never got sadder. —Rob Harvilla

44. "Tyrone," Erykah Badu

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

The second-best moment on this viciously sultry slow jam, the crown jewel of Erykah Badu'south 1997 anthology Live, is the stupendous opening line: "I'grand gettin' tired of your shit / You lot don't ever buy me nothin'." The showtime-best moment is all the women in the oversupply immediately shrieking with delight and, 1 fears, recognition. "Tyrone" is named for 1 of an unnamed deadbeat lover'due south numerous deadbeat friends: "Every time nosotros go somewhere," Badu purrs with lethal authority, "I gotta achieve down in my purse / To pay your way and your homeboy'due south way and sometimes your cousin's way." It is the gender-flipped riposte to Fri's "Farewell, Felicia," and in fact turned up as a joke in 2000's Adjacent Fri; it "followed me thru my career similar an obsessed Ten boyfriend," equally Badu put information technology on Instagram in 2017, while shouting out her backup singers, whose sardonic and sublime "Call him!" dirge is the tertiary-best moment. —Harvilla

43. "Love Is a Battlefield," Pat Benatar

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

The agonizingly propulsive signature striking from flamethrower-voiced '80s pop queen Pat Benatar laments not then much a breakdown as a near-breakup in progress, an acknowledgement that true beloved means almost breaking upwards pretty much all the time: "Believe me / Believe me / I tin can't tell you why / But I'thou trapped by your honey / And I'm chained to your side." It's a karaoke archetype you have no business organisation attempting, a cheeseball Reagan-era nail of eternal profundity, and a striking declaration that sometimes the only affair worse than splitting upward is not splitting up: "Do I stand in your way / 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

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

We're not fifty-fifty talking near the whole vocal—we're talking about 20 or so seconds of Bink production afterward Kanye'due south second verse, only before Rick Ross's only verse, arguably one of the all-time in his career. In it, he describes Westward's near-fatal motorcar crash in 2002 as an aborted climb "upwardly the Lord'southward ladder," and honestly, that'due south exactly what the collection of power strings audio like on this bridge. A climb upwards the Lord's ladder, a divergence from Earth, a one-manner trip to anywhere but here. —Micah Peters

41. "Suspicious Minds," Elvis Presley

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

Yous can run into the ripples of "Suspicious Minds" throughout the course of breakup song history, from "Train in Vain" to "Dancing on My Own," which, you know, it's Elvis. But beyond the juxtaposition of its relatively upbeat music and depressing-as-hell lyrics, I love the construction of this vocal, with a peppy guitar intro and verses that build into a chorus that goes from Thou major to very, very Due east minor and just doesn't e'er actually resolve. This might not be the but reason the vocal fades out but there's no real suitable ending betoken for the last notes of the chorus, so it always drops back into a poetry or a bridge or some other chorus. "John Jacob Jingleheimer Schmidt" resolves more easily. Just like a broken relationship. —Baumann

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

Most heartbreaking lines: "Although she may be cute, she's merely a substitute / Because y'all're the permanent one"

On this classic Motown tearjerker, Smokey embodies the idea of the lamentable clown meliorate than any song always has. He's the life of the political party—using jokes like a clown uses makeup—just inside, he'south wounded, pining for a past lover. He's dating someone new, but he's non thinking of her. (Side note: I don't know who I'm sadder for hither, Smokey or the rebound he's walking around town with.) He may accept wiped away the tears, only they've left their marker. And the makeup merely makes the tear tracks that much more credible. —Justin Sayles

39. "Tears Dry 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 be some side by side homo's other adult female presently"

On "Tears Dry on Their Own," Amy Winehouse demanded that Amy Winehouse have her ain advice. "I cannot play myself once again, I should just be my own best friend," she warns. "Not fuck myself in the caput with stupid men." These lines that pried the song open were i of Winehouse's hallmarks as a writer—"Tears" begins in the dumps, in the backwash. But during every emotional uncoupling comes the signal where you gaze into the mirror, stick your finger in your reflection's breast, and tell them to stop beingness such a dumb, whiny baby. —Peters

38. "Needed Me," Rihanna

Almost heartbreaking lines: "Fuck your white horse and a carriage / Bet y'all never could imagine / Never told you you lot could have it / You needed me"

This song is so little and I love it. Rihanna basically made a hit off the "Sike, y'all thought!" meme and DJ Mustard added an unforgettable beat backside it. This is one of those bangers that you and your girls blast mail-breakup, pre-going-out. So, after yous all sing in unison: "Don't get it twisted / Y'all was just another nigga on the hit list / Tryna fix your inner issues with a bad bitch," you all flare-up into laughter thinking about the homo who is now barely a retentivity. Rihanna'south confidence and savageness is really on an untouchable level. (Remember, this vocal is on the aforementioned album where she sings "sexual activity with me is so amazing" over and over.) Long may she reign. —Jordan Ligons

37. "So Sick," Ne-Yo

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

The earworm of a generation! Ne-Yo said no to sappy ballads in more than ways than one with "Then Sick," giving the states an R&B smash hit for everyone sick of regular, schmegular dear songs. Set to the world's catchiest beat, Ne-Yo mourns a past relationship and all the day-to-twenty-four hours changes that come with moving on. "Gotta alter my answering machine, now that I'm alone / 'Cause correct now it says that nosotros tin can't come to the telephone … Gotta set that agenda I have that's marked July 15 / Because since at that place's no more you, at that place's no more anniversary." Fifteen years subsequently, we yet can't turn off the radio. —Halliwell

36. "We Vest Together," Mariah Carey

Nigh heartbreaking line: "When you lot left I lost a part of me / Information technology's even so so hard to believe / Come back baby, please / 'Cause we belong together"

*Sighs.* This is hands 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. Only now if it comes on the radio and y'all're either happily single or in a solid relationship, your optics volition glaze over, guaranteed. When the starting time two seconds of the infamous beat come through my speakers, I'g already changing the station. Information technology'due south but and then annoying, and then Mariah.

You may remember that you lot won't observe someone else to lean on when times get rough or someone to talk to yous on the phone until the dominicus comes up, only let me tell you, you will and you'll be fine. Breakups suck, but please don't torture your broken heart (or your ears) past listening to this song on repeat. —Ligons

35. "If You See Her, Say Hello," Bob Dylan

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

The inspiration for Bob Dylan's masterful Blood on the Tracks has always been debated. Critics have long assumed that the album is near Dylan's separation from his wife, Sara. The couple's son, Jakob, reportedly believes that Blood is virtually his parents. Only Dylan himself has steadily denied that his masterpiece is autobiographical, even saying instead that it's based on … Chekhov'southward brusk 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 almost palpable on "If You See Her, Say Hi," which brings us into a fractured relationship in a fashion that's both effortlessly relatable ("We had a falling out, like lovers often will") and hyper-specific ("And to recall of how she left that dark, information technology still brings me a chill"). It's not Dylan's flashiest or heaviest or best vocal, but it is my favorite, a gentle, intimate portrait of lost dear and lasting ache. Like so much of his best work, it'south propelled by its poesy, the raw insights virtually how it feels to be alive. The song cycles through the same phases that then many of us do while processing heartbreak: denial, despair, acrimony, desire. It floats on a current of remorse ("Sundown, yellow moon, I replay the by / I know every scene by eye, they all went past so fast") yet manages to convey the kind of longing that leads, cautiously, back toward hope ("If she's passing back this way, I'one thousand not that hard to notice / Tell her she can look me upwardly, if she'south got the time"). After enough listens, and enough heartache of your own, you realize that "If You lot See Her, Say Hello" isn't really a breakup song. It'due south a dearest letter. — Mallory Rubin

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

Virtually heartbreaking line: "Stand up beside the fireplace / Have that look from off your face up / 'Cause you ain't ever gonna burn my heart out"

The closest I've ever come to living in an episode of Glee was when my high school French course spontaneously broke out singing "Don't Wait Back in Anger." I don't remember why, only it cemented this vocal (at least for me) as a ballad of communal weltschmerz, rather than personal sadness or regret, like a fin-de-siècle "You'll Never Walk Solitary." (For instance: "Don't Look Back in Anger" became a kind of unofficial canticle afterward the Manchester bombing in 2017.) Oasis knows a affair or two about writing for the communal sing-forth, the importance of the languid, memorable melody and the propulsive chord change—this song would conduct about the aforementioned emotional weight if information technology were but a title and a chorus. —Baumann

33. "Every Breath You Take," the Constabulary

Nearly 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 Moving ridge ballad, which anchored the Law's 1983 goliath Synchronicity and reigned every bit one of the biggest radio hits of the decade, is creepy every bit all hell, very much past design: an unrepentant stalker manifesto that doesn't and then much describe spurned dearest in terms of surveillance as it describes full state surveillance in terms of spurned love: "Every move y'all make / Every vow y'all suspension / Every smile you lot faux / Every claim you stake." And so on. "I'll be watching you," Sting concludes a couple dozen times throughout, but it'southward the chest-pounding bridge where the trio'due south creepy-soulful frontman does some of his best belting, his all-time pleading, his all-time 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, simply 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 hands, 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-rock song. It also takes a lot of guts to write a song nearly breaking up with the bass player in your band and and then make a music video for the song that has shots in information technology like the one below: Don't speak, literally.

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

31. "Thinkin Bout You," Frank Bounding main

Nearly heartbreaking lines: "Do you not retrieve 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 tin can practise better. I didn't love them, I only idea they were cute. Frank Ocean's "Thinkin Bout You" exposes that kind of posturing for what it is: a facade. No, I wasn't crying nigh you lot, and by the mode, I besides own waterfront belongings in Idaho. Frank's clearly nonetheless hung up on the past fifty-fifty if his former flame isn't. And the simply way to piece of work through the pain is to drop the lying and come clean with himself. It's tender, it's sugariness, but nearly of all, it's honest. —Sayles

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

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

No matter your current relationship status, yous will for sure sing your heart out when this song comes on. I do not care, I am Mary J. when the chorus hits. By the terminate of the song—a cover of Rose Royce's 1976 single—you've "gone down" and then much that y'all're on the floor, eyes closed, hoop earrings in, and belting, "My whole world's up-[dramatic intermission]-side down!" I can't be the only one, right?

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

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

Most heartbreaking lines: "I could put my arms around every boy I come across / Simply they'd only remind me of you"

Breakups are freeing; breakups are imprisoning. When you come out of a yearslong human relationship, you take to relearn how to live without that person in your life. Parts of that procedure are beautiful—reconnecting with old friends, picking upwards a new hobby, shaking off the shackles. But the breakup sticks with you. You run into your ex's all-time friend at the bar, or you hear a song that you both loved. Sometimes, information technology's a pocket-sized badgerer. Other times, it'southward an earth-shattering event. You lot're relearning how to live, but living is difficult.

I can't think of a song that better captures that duality than "Nothing Compares 2 U," the 1990 O'Connor striking originally penned past Prince in 1985. Y'all can do any y'all want: Yous can party all night, you can eat at a fancy eatery, yous can put your arms around all the boys and girls you'd like, but it doesn't matter. Information technology'southward not them, and aught will be. Your best promise is just giving in and living for yourself. —Sayles

28. "Marvin's Room," Drake

Near heartbreaking line: "The adult female that I would try / Is happy with a skillful guy"

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

27. "Just a Friend," Biz Markie

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

Turns out this woman did not have what Biz Markie needed. As he singsplains, he became kitten smitten with a woman at 1 of his shows. You lot'd call up that this would have happened to him all the time, but it did not. This was "the first girl I always talked to," Biz told EW last year. "Every time I would call out to California, a dude would selection upward and paw her the phone. I'd be like, 'Yo, what's up [with him]?' She'd say, 'Oh, he'southward merely a friend. He's nobody.'" Not taking the hint, Biz flew out to California to surprise her a week earlier than planned. When he showed up, there was a guy "tongue-kissing my daughter in her mouth."

Biz. My guy. Sit down down. Let's talk. Showtime off, she was not your girl. Yous met her one time. 2d, you did not take hold of her natural language-kissing a dude. Y'all stalked her. 3rd, 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 about his predicament. You know, a friend. —Danny Heifetz

26. "Burn," Usher

Most heartbreaking line: "Simply yous know, gotta let it become / 'Crusade the party ain't jumpin' like it used to / Even though this might bruise you / Permit it burn"

I couldn't imagine someone breaking up with me with the lyrics to this song. Usher is all over the place. He says he loves me, only our human relationship has to come to an cease; he says he's hurting and he'due south not happy, but he'south breaking down and crying. Deep down he knows it'southward best, but he hates the thought of me beingness with someone else. Become your shit together, Usher!

Still, for all of its confusing back-and-forth, this is a breakdown archetype. It preaches the credo of forcing yourself to let go even when y'all don't know what you're going to do without your boo. Later on a heartbreak, everyone has establish themselves teetering on the line betwixt regret and liberty. Usher's "Burn" allows you to tap into that while simultaneously yelling out, "It'south been fifty-xi days, umpteen hours, and Imma be burnin' till you return!" —Ligons

25. "Slice of My Heart," Large Blood brother & the Holding Visitor

Most heartbreaking line: "But each fourth dimension I tell myself that I, well I tin't stand up the pain / Merely when you hold me in your artillery, I'll sing it once again"

If yous're ever at your wits' cease, tragically obsessed with someone who treats you like shit, you can discover some catharsis in the controlled anarchy of Janis Joplin'southward vocal functioning on "Slice of My Middle." Get alee and scream along. Yous won't sound equally adept as Janis, simply y'all'll certainly feel a hell of a lot better subsequently.

In one case your acrimony fades a little, you can switch over to the original recording of this song, released a year before in 1967 and sung by Erma Franklin (yep, that's Aretha's older sister). Or if y'all demand some more twang accompanying your despair, you can endeavor the Faith Loma version. I also won't approximate you if the only person who tin ease your pain is Shaggy (or Beverley Knight, Melissa Etheridge, Steven Tyler, Kelly Clarkson, or one of endless other artists).

Written past Jerry Ragovoy and Bert Berns, "Piece of My Heart" is 1 of the most relatable and enduring songs nearly Some Fuckboi in the history of fuckbois. The call-and-response structure of the chorus builds those simmering resentments and releases them with a precipitous, primal cry. Undoubtedly, there will be new versions of this song until the end of time⁠—because it's an absolute banger—simply also because … men. —Matt James

24. "Skinny Love," Bon Iver

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

A good rule for breakdown songs is that there has to exist a office that you tin can yell forth to, unencumbered by silly things like constraint and cocky-awareness. The chorus of Bon Iver'south "Skinny Love" has a smashing one, specially for anyone who'south only exited a relationship and feels compelled to heap all the blame on the other party.

You know the story by at present: In 2006, Justin Vernon broke upwards with his girlfriend, packed up his car, and drove into the Wisconsin wilderness, emerging only afterward recording an album of weepy breakdown songs. That origin tale has been repeated so ofttimes that it's go soft mush, obscuring the real truth: That For Emma, Forever Ago—and especially "Skinny Love"—are profoundly reflective, intelligent, moving documents nigh the breakdown of a relationship. —Gruttadaro

23. "Hold Upward," Beyoncé

Virtually heartbreaking line: "Can't you see in that location's no other man above you? / What a wicked way to treat the daughter that loves you"

It's hard to express real hurt over an uptempo shell and brand the heartbreak disarming. Yet Beyoncé is believable in "Concord Up," a painful accounting of the emotions that come afterwards discovering that your partner has cheated. Lemonade was inspired past truthful events—i.e., it'southward Beyoncé coming to terms with Jay-Z being unfaithful. Infidelity brings on a very specific type of destruction: You're mad; y'all're miserable; yous're humiliated. You switch from one emotion to another in a affair of minutes. She opens the song with confidence: No other woman can give what she can. "Concord up, they don't love yous like I love you." In a breath, she's less sure of herself: "What'south worse, looking jealous or crazy?" Beyoncé settles on crazy, then returns to anger. "Y'all allow this good love become to waste product." —O'Shaughnessy

22. "Cry Me a River," Justin Timberlake

Most breaking lyric: "You didn't know all the ways I loved you, no / So you lot took a adventure / And made other plans"

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

In his beginning solo megahit, Justin insinuates his love has cheated on him ("You don't accept to say what you did / I already know, I institute out from him") and writes her off for good. He'due south already cried almost it, and now it'due south her plough. But no corporeality of her tears can undo the impairment; he'southward gone. You didn't have to practice much sleuthing to effigy out he was singing about Britney. That celebrity intrigue, Timbaland's abrupt product, and an instantly memorable music video combined to make "Cry Me a River" the most iconic breakup song of the early 2000s, catapulting him to some other level of distinction. He had split with not only Britney, merely also his by, and he was ready for the globe. —Sayles

21. "With or Without You," U2

Near heartbreaking line: "She got me with nil to win / And zilch left to lose"

Nothing changes if nothing changes, as they say, and "With or Without You" exists in that hopelessly recursive "I detest that I honey you lot" space. This vocal was U2's commencement no. ane hitting in the U.S., even though, Bono has said, "information technology'southward a very odd-sounding vocal … it kind of whispers its way into the world." But information technology's not the whispers that resonate nigh, however, it'southward all those wails, similar the crescendo of Bono's aching, eminently singalong-able ahhh-ahhh-ahh-ahhhhhs, or the painful, everlasting notes from the Border's "infinite guitar," engineered to agree a tone equally if it were a grudge. "Psychotic restraint" is how Bono characterized the Edge's spare piece of work on this track, a description that could double every bit breakup advice. —Katie Baker

20. "Jolene," Dolly Parton

Most heartbreaking line: "And I can hands sympathise / How you could easily accept my human being / But you don't know what he means to me, Jolene"

While other female person country singers might've handled their man's newfound fascination with a beautiful redhead by, say, earthworks a key into the side of his pretty little souped-up iv-cycle drive, or—just spitballing here—threatening to send her to Fist City, Parton simply pleads for mercy. The desperate pitch of her appeal, set against a frantic Dorian-mode guitar riff, sets the stakes far higher than those you might find in mostly stern state songs most cheatin', lyin', and being untrue. Whatever armchair scholar of Parton'south work can tell you lot she cloaks feminist manifestos within marketable diddies well-nigh everyday experiences. I've always taken the song'south urgency to imply something that every woman learns somewhen: Relationships can exist both romantically fulfilling, and, likewise ofttimes, an economic lifeboat to a better 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 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 anthology In the Groove. Mayhap the song resonated with Gaye because he married a 41-year-one-time adult female when he was only 24, and their union was total of infidelities. "I was in beloved with the thought of dearest," Gaye in one case said. Or at least that'due south what I heard through the grapevine. —Heifetz

xviii. "Ex-Factor," Lauryn Hill

About heartbreaking line: "Where were you when I needed you lot?"

"Ex-Gene" is more than than a breakup song, information technology's about recognizing a toxic relationship before you lot have the words to telephone call it a toxic relationship. Each line, so honest it hurts, is about the fruitless search for reason in a scenario devoid of it. Hill's lyrics capture the worst of the worst of a relationship on the rocks: the pain, the complicity, and the unwillingness to give upwardly on a dearest you recall is still there, cached beneath the bullshit.

When it striking airwaves again in 2018 on Drake's pandering yet irresistible "Overnice for What," it was almost like recognizing and reclaiming a past self—one who might have cried along to the original. At present, as wiser, more Empowered™ listeners, we heard the remixed, tricky hook devoid of its devastating verses and bopped our heads every bit Drake reminded us of how short life is. However, no one can capture the raw, uncomfortable emotion that Lauryn originally did—and no one ever will. —Johnson

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

Nigh heartbreaking line: "Well, you said that we made such a pretty pair / And that you would never get out / But you gave away the things y'all loved / And 1 of them was me"

Far earlier Taylor Swift sent her fans on subtweet scavenger hunts, Carly Simon penned a ballsy kissoff that, thanks to its cocky-referential chorus, left the world wondering whom it was about and what they could've peradventure done to anger her. More than forty years of speculation afterwards, nosotros at present know that the vocalist was describing the thespian Warren Beatty. (She added in a recent, withering interview that, although the song describes 3 separate men, Beatty "thinks the whole thing is about him.") We may never know what company he kept (cough: Mick Jagger?), but the lasting power of Simon's articulate-eyed takedown stands every bit a referendum on the unchecked male ego, whether its contained in the body of a dashing thespian or a moody fuckboy. —Bereznak

16. "Dancing on My Own," Robyn

Most heartbreaking line: "Yeah, I know information technology'southward stupid, I but gotta see it for myself"

Concluding year, post-obit a Robyn show at Madison Foursquare Garden, elated concertgoers continued the party on the A/C/E train subway platform, breaking into a lightheaded public operation of "Dancing on My Own." You wouldn't typically expect a breakdown song to exist the i that leads New Yorkers to such displays of collective joy, only well-nigh breakup songs aren't like this one: a song yous tin can strut to, a gild canticle, a scene-stealer, a story of lonesomeness that still finds its solace in a oversupply. It'south a song near moving on—I just came to say goodbye—but also most, merely, moving. The vocalist might exist alone in the corner, and she might know it'due south stupid, but she's out at that place dancing, at least. —Baker

fifteen. "Thank U, Next," Ariana Grande

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

This song is a determination to exist done with suffering over a human relationship, to recommit to oneself, to focus on healing and establishing new patterns. To non only rehearse past losses but to envision future victories, and also to alive in the moment, to be here now.

This to practice the actual, day-in, twenty-four hour period-out piece of work of being happy. —Peters

fourteen. "End of the Route," Boyz 2 Men

About heartbreaking line: "It's unnatural"

Both the joyous genesis and abject death knell for billions of '90s junior-high-gymnasium-dance relationships that only lasted the length of the song itself, "Finish 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" large. Like, "The 'Former Town Road' of Its Day" big, a tearjerking shout-along anthem for lovelorn belters too devastated to even take their horses and leave the house. The final a capella chorus is a signature moment in American cultural history, at in one case exhilarating and devastating: "It's unnatural / Yous belong to me / I belong to you." The give-and-take unnatural has never sounded so natural, and and then miserable. —Harvilla

xiii. "Dreams," Fleetwood Mac

Nearly heartbreaking line: "Now here you lot go over again, you say yous want your freedom / Well, who am I to go along you lot down?"

Fifty-fifty 40-plus years on, to hear Stevie Nicks softly moaning, "What you had ... and what you lost / And what you had ... and what you lost" to the guy playing guitar is to live forever, and to imagine that guitar player dropping dead from remorse on the spot. (Lindsey Buckingham, of course, has been known to belt out a sweetly caustic breakup canticle or two himself.) As the second (and all-time!) rails on 1977'due south zillions-selling Rumours, "Dreams" is both radically overexposed and even so somehow criminally underrated, fixed to its iconic place, time, and circumstances merely also shockingly timeless. (Zoë Kravitz rhapsodizes it in the pilot of Hulu's new High Fidelity remake series to bear witness her stone-nerd bona fides.) Pair it with "Silver Springs" for maximum effect. —Harvilla

12. "How Tin can Yous Mend a Cleaved Middle," Al Green

Most heartbreaking line: "Permit me alive again"

There's heartbreak, so there's Al Green heartbreak. (Not to slight the original Bee Gees version—Green is all I know when I'm going through it.) He'southward exasperated from the start, wondering whether he'll e'er recover from the dear that went away. The agony is enough to contemplate nature itself in the chorus: "How can y'all mend a broken eye? / How can you stop the pelting from falling down? / How tin yous end the sun from shining? / What makes the world go round?" Green is begging for answers, for "somebody, please" to come set up him. He pleads, "Let me live over again." Life equally he knew it is over without this person, and every bit long as the vocal is on, it feels over for us, too. —O'Shaughnessy

xi. "Torn," Natalie Imbruglia

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

There's a bad breakup, there'southward rock bottom, and then there'southward being "cold and shamed, lying naked on the floor." Natalie Imbruglia's 1997 1-hitting wonder (and sneaky embrace) doesn't mince words in describing exactly how shitty it feels to put your faith in the wrong human being. (Or whatever human, depending on how hard you vibe with this song.) "Torn" has taken a turn for the over-covered and over-memed these days, only you're lying if you say you don't still hit that chorus every time. —Halliwell

10. "I Volition Survive," Gloria Gaynor

Well-nigh heartbreaking line: "So you felt like dropping in and just expect me to exist gratuitous / Well now I'm saving all my lovin' for someone who's lovin' me"

This 1978 disco colossus is and so atypical, then monolithic, so hymeneals-dancefloor-ingrained that information technology hardly scans equally a breakup vocal at all: Equally ecstatic and empowering fuck-you anthems go, it is the glamorous grandmother to Lizzo's "Truth Hurts" and Ariana Grande'southward "Thank U, Adjacent" and Beyoncé's "Irreplaceable" and roughly l,000 other self-affirming pop hits. What truly elevates New Jersey diva Gloria Gaynor'due south all-timer, though, is its sociopolitical import: "I Will Survive" has long been a stirring battle hymn for the LGBTQ community, for survivors of domestic violence, for anyone who can relate in any way, frivolously or otherwise, to the frankly iconic line "I'thousand saving all my lovin' for someone who's lovin' me," which of course is everybody. She knows you're afraid; she knows you're petrified. Only she also knows you won't stay that way for long. —Harvilla

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

Nearly heartbreaking line: "Wonder this fourth dimension where she'south gone / Wonder if she's gone to stay"

To brand a song from 1971 about a video game from 2010: Dante'due south Inferno is an RPG based loosely on the first canticle of the Divine One-act. I say loosely because EA Dante has rippling muscles and a massive scythe, his only protections against the legions of the dark, who've stolen his dear Beatrice. I never played it, only a friend who did described his frustration with the game: Information technology'due south every bit if its decision got further away the more fourth dimension he devoted to it. A Super Bowl commercial showed Dante sprinting toward Hell's gaping oral fissure adamant but, you know, definitely doomed. Every bit he descends you hear the low croak of Bill Withers's vocalization, pining afterwards a lost lover: "Ain't no sunshine when she'south gone, but darkness everyday." My last breakdown didn't involve a giant flaming devil monster, but it did feel like a similarly hopeless uphill battle. —Peters

8. "Someone Like You," Adele

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

The queen of heartbreak has never been better than on sophomore album 21, and 21 doesn't get much ameliorate than "Someone Similar You." Adele's ode to the one who got away is perhaps the near universally adored tearjerker of the past decade; starting with that simple piano line and ending in that burdensome hook: "Sometimes it lasts in love, but sometimes information technology hurts instead." And of grade, that vocalization! Watching the simple black and white music video at present, it's striking how baby-faced Adele was at 21, despite her commitment of a song that displays so much emotional maturity. She wishes the best for her ex ("Erstwhile friend, why are you and then shy?"), but damn, she'southward nevertheless hurting. Aren't we all! —Halliwell

seven. "I Want You Back," The Jackson five

Near heartbreaking lyrics: "Someone picked you from the bunch, ane glance was all information technology took / Now it's much too tardily for me to take a second expect"

Maybe the almost outwardly joyous song in this unabridged ranking, "I Want You Back" spins a tale that anyone who's ever taken someone for granted volition understand. An eleven-year-quondam Michael Jackson is at his most precocious here, singing about the girl whom he didn't fully capeesh until someone else stole her heart. At present he just wants another take chances to prove that he knows how to treat her right. Michael, of course, didn't write the song—information technology was penned by Drupe Gordy and Co.—but he sells it in a fashion that someone 2 or three times his historic period never could. A leopard can't change its spots, but if it sounds this adept trying to convince you lot it tin can, why not give it one more adventure? —Sayles

6. "Since U Been Gone," Kelly Clarkson

About heartbreaking line: "How come up I'd never hear you say / 'I only wanna exist with you' (exist with you) / I guess y'all never felt that way"

There is a moment in every breakup where, later on a few weeks of self-pity, you lot shed your sweatpant cocoon, step outside, and, with the instantaneity of a rubber band snap, all of a sudden know deep within your heart that your ex was an insufferable blowhard. Kelly Clarkson's mosh-adjacent ability popular carol embodies the newfound cocky-assurance that comes with that realization. It also happens to be enshrined in a pop civilization moment that I volition forever acquaintance with being a melodramatic 16-year-old 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 poetic Yeah Yeah Yeahs hit, "Maps," and then—later being passed upwardly past both Pink and Hilary Duff—was sung by the very offset winner of the then-fledgling reality Idiot box bear witness American Idol. The AIM-friendly "U" in the title is just the icing on the block. —Bereznak

five. "Ms. Jackson," Outkast

Most heartbreaking lyric: "Forever never seems that long until you're grown / And detect that the 24-hour interval-by-day ruler tin't be as well incorrect"

Sometimes breaking up with your pregnant other's family is just every bit hard as breaking up with them. Big Boi and André 3000 understood that on "Ms. Jackson," a song defended to Kolleen Maria Wright, the female parent of Erykah Badu, with whom André had a child. Iii Stacks's verse is especially poignant—his intentions were good, but things took a turn for the worse. It's a harsh reality: Most relationships are born with an expiration appointment, no matter how bright the flame burned at the beginning. Equally far as apology songs go, it's pretty nuanced and sincere. And Wright seems to have bought it: Erykah said in 2016 that her female parent even has a "MSJACKSON" license plate. —Sayles

4. "I Will Always Beloved You," Whitney Houston

Most heartbreaking line: "Please don't cry / We both know I'm not what y'all, you demand"

Dolly Parton wrote one of the most dynamic love songs e'er with "I Will Always Honey You." Whitney Houston, who sang a cover for the movie The Babysitter, made a worldwide hit with her phenomenal range. Both versions are wonderful for different reasons, though Parton's honeyed, wobbly original is all-time for heartbreak. For one, information technology's authentic: She wrote the song for her old managing director and professional person partner, Porter Wagoner, after she decided to leave him. Parton is sympathetic, yet determined to go. Every bit she sings in the span, it's bloodshot. They are both amend off this way, she argues, only wishes him nada simply "joy and happiness." 1 of the hardest relationship lessons is that two people tin love each other and it still not be right for either—thanks to Dolly and Whitney, it was 1 learned early. —O'Shaughnessy

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

Most heartbreaking line: "I'll close my eyes / So I won't come across / The dear y'all don't feel when y'all're belongings me"

Yous might be a girlfriend, a husband, a partner, or even a friend with benefits. Whatever role y'all play in service of love, it comes with a label 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 beloved lives is that love itself can be a ruthlessly nonbinding agreement, an at-will organisation. Even more frightening is that it's often our hearts—non usa—calling the shots.

What sets "I Can't Make Yous Love Me" apart from well-nigh breakdown songs is that information technology takes identify at the most painful bespeak of a breakup: acceptance. It's non a post-breakup anthem of empowerment or a desperate plea to stay together. It's the full strength of the disorienting one-two punch of loss and loneliness. Information technology's the world-shattering moment when you give upwardly the fight.

Bonnie Raitt's arresting performance of this song (written by Mike Reid and Allen Shamblin) carries the weight of a lifetime in and out of love. She sets downwardly her slide guitar, sits Bruce Hornsby downward at the piano, and sings the absolute fuck out of this song with conviction and grace. The song used on the Luck of the Describe album recording was Bonnie'due south first take. "I Can't Make You Dearest Me" has been covered by countless artists, included on several Greatest Songs Of All Fourth dimension lists, and inducted into the Grammy Hall of Fame.

The songs that bear upon u.s.a. nearly deeply are the ones that unite us through the most human of shared experiences. Eventually, nosotros all learn that y'all can't make someone's center feel "something it won't." But should you one 24-hour interval find yourself at rock bottom, of a sudden alone in darkness—whether it'southward your start time or your 14th—yous tin feel a little bit less alone knowing that Bonnie's been there, as well. —James

2. "Yous Oughta Know," Alanis Morissette

Most heartbreaking line: "Does she know how you told me you'd hold me until you died, till you died / Only y'all're yet alive"

Alanis Morrisette was 19 years old when she recorded that carol of bitterness "Y'all Oughta Know" in one take at 11 p.grand. "All those vocals are merely her at the end of the nighttime," said her cowriter Glen Ballard in an oral history of the album Jagged Lilliputian Pill, "singing something she just 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 possibly inspired by Uncle Joey remains both iconic and securely weird, but also makes sick sense: Y'all haven't truly been jilted until y'all've been jilted past someone who's not fifty-fifty that cool, you know?) "You Oughta Know" totally scandalized my mom every time it came on the radio in the '90s, and what's more, information technology features both Flea on bass and Dave Navarro on the guitar. What more than could you desire—other than sweet, sweet vengeance? —Baker

1. "Imperial Rain," Prince

Near heartbreaking line: "I never meant to cause y'all any sorrow / I never meant to crusade you lot any pain"

Purple rain, co-ordinate to an unsourced quote that'south widely attributed to Prince Rogers Nelson, is the event of blood mixing with the sky, which is a sort of apocalyptic drama that only Prince could conjure. Just you don't fifty-fifty need to sympathize what purple rain is to experience "Majestic Rain," a power ballad to end all power ballads.

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

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