Everytime We Make Up and Break Up and Then Do It Allover Again

What makes a song a "breakup vocal"? Does it have to exist empowering, à la "I Will Survive" or most of the songs on Lemonade? Should it be for the lonely, similar Carole Male monarch's "Information technology's Too Belatedly" or Bob Dylan'southward "If Yous See Her, Say Hullo"? 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 nigh his divorce.) What virtually songs with a famous backstory, similar "Cry Me a River" or any track off of Rumours?

We hither at The Ringer believe that since heartache comes in many forms, so should the breakup song. And in honor of Valentine's Day, we decided to dig deep into the genre. Beneath, you'll find our ranking of the 50 greatest breakup songs of all time, equally voted on by our staff. The listing spans several decades and many different moods, simply all are rooted in some type of hurting. At that place was but ane rule for the terminal ranking: simply one vocal per artist was included to avoid Dolly Parton or fifty-fifty Drake from dominating.

So if you're lonely, fire upwardly our playlist and weep along as yous read our thoughts on each entrant. If you're happily attached, you tin can still dive in—these are some of the greatest songs ever recorded, and that's truthful whether you lot're in your feelings or not. Possibly you'll gain a greater appreciation for your electric current relationship. Later on all, breakup songs resonate only when you lot know what it'due south like to lose in love. —Justin Sayles

50. "Nosotros Are Never Always Getting Back Together," Taylor Swift

Well-nigh heartbreaking line: "You lot would hide away and observe your peace of listen / With some indie tape that'due south so much libation than mine"

One of the about savage breakdown songs in history, "We Are Never Ever Getting Back Together" encapsulates the severe "fuck that guy!" energy that follows a long-overdue departing of ways. We've all had that mail service-fight rant with our friends: "Ugh … so he calls me up and he's like, 'I even so dearest y'all,' and I'm similar … 'I merely … I mean this is exhausting, yous know, similar, nosotros are never getting back together. Like, ever.'" Flippant, triumphant, and entirely exhausted by All Men, Taylor Swift gave us the perfect soundtrack for breakup recovery. — Kate Halliwell

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

Virtually heartbreaking line: "I need somebody and always / This ill foreign darkness / Comes creeping on then haunting every fourth dimension"

"I Miss Y'all" is like a minimalist/emo take on Meat Loaf. It rules. The two best things most this number are Travis Barker's simple but persistent drumbeat and Tom DeLonge'south entrance on the second verse. It'due south part of the grand pop punk tradition of showing you mean business organization by going upwards an octave, of which "I Miss You" (forth with the Starting Line'southward "The Best of Me") is the exemplar.

Don't just take my give-and-take 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'south Too Late," Carole Male monarch

Most heartbreaking line: "Merely we just can't stay together, don't you feel it, also? / Still I'm glad for what nosotros had and how I once loved you lot"

"Information technology'south Too Late" is a burdensome ode to the well-nigh common kind of breakdown. The natural process of two people growing apart is as heartbreaking as it is commonplace, and King sings in a tone perfectly situated betwixt her sorrow and the shrugging admission that "nosotros really did try to make it." Her conversational commitment early in the vocal brings united states into the living room, diner, or sidewalk where "the talk" betwixt her and her nighhoped-for-ex is happening: "Ane of us is changing, or perhaps we just stopped trying," she sings, patently laying out the cardinal, blameless reasons for why well-nigh people terminate upwards separating. The song is defined by its maturity and its conciliatory attitude, only every bit with actual breakup conversations, that doesn't make information technology any easier to hear. —Cory McConnell

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

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

This is a perfect case of the kind of breakup vocal you hear on the radio (or, in the late '90s, possibly the club—the Frankie Knuckles house remix withal goes) and, on a normal day, just hear another pop vocal, but when yous're experiencing heartache, what originally sounded similar songwriting clichés become the truest words yous've ever heard. "I accept cried a lot of nights," you think, getting out of bed for the starting time fourth dimension in days to grab a curl of toilet paper since yous ran out of Kleenex. "Life is fell without you here beside me," you murmur, staring into the bleak chasm of loneliness y'all now know equally life. "I would literally practice anything on God's greenish earth to hear yous say you dearest me again," you realize with the greatest clarity you've e'er 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 breadbasket is sick / And it's all in my head"

Maybe it'due south non exactly correct to call "Mr. Brightside" a breakup vocal; maybe it'south more accurate to telephone call information technology a right-before-the-breakup song, an I-imagined-my-girlfriend-was-cheating-on-me-then-intensely-that-she-actually-started-cheating-on-me song. But that's all actually clunky, and then let's have existence slightly incorrect for the sake of cleanliness. Either style, "Mr. Brightside" is an iconic mid-aughts song that'due south perfect for yell-karaoking and that pulls off the difficult trick of but repeating ane verse over and over. Also, Eric Roberts in the video. —Andrew Gruttadaro

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

Near heartbreaking line: "Get upwardly in the morning, look 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 ascension to greatness begins here, with the breakout hit from their 2nd album, 1973'southward oddly/heartbreakingly named Abandoned Luncheonette. "She's Gone" is luscious and silky and deceptively light, all Motown grandeur past way of blue-eyed Philly soul, but that lightness only underscores the exquisite heaviness of murmured verse lines like "Get up in the morning, expect in the mirror / Worn every bit the toothbrush hanging in the stand." (Or probably it'southward "1 less toothbrush," which of course is even heavier.) The chorus, by contrast, is gigantic and purple and crushing, punctuated past cloudbursting lamentations of "She'due south gone! / Oh why? / Oh why?" The boys but got bigger from here, just they certainly never got sadder. —Rob Harvilla

44. "Tyrone," Erykah Badu

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

The second-best moment on this viciously sultry dull jam, the crown jewel of Erykah Badu'southward 1997 album Alive, is the stupendous opening line: "I'yard gettin' tired of your shit / You lot don't always buy me nothin'." The first-all-time moment is all the women in the crowd immediately shrieking with delight and, i fears, recognition. "Tyrone" is named for one of an unnamed deadbeat lover'due south numerous deadbeat friends: "Every time nosotros go somewhere," Badu purrs with lethal potency, "I gotta reach downward in my purse / To pay your way and your homeboy's way and sometimes your cousin'due south fashion." Information technology is the gender-flipped riposte to Friday's "Bye, Felicia," and in fact turned upward every bit a joke in 2000'south Adjacent Friday; it "followed me thru my career similar an obsessed X young man," as Badu put it on Instagram in 2017, while shouting out her fill-in singers, whose sardonic and sublime "Telephone call him!" dirge is the 3rd-best moment. —Harvilla

43. "Dear Is a Battlefield," Pat Benatar

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

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

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

Nigh heartbreaking line: "Throwing shit around, the whole identify screwed up / Maybe I should phone call Mase and then that he could pray for united states"

We're not fifty-fifty talking virtually the whole song—we're talking about 20 or so seconds of Bink production afterward Kanye'due south second poetry, but before Rick Ross'due south only poetry, arguably one of the best in his career. In it, he describes West's virtually-fatal car crash in 2002 as an aborted climb "up the Lord's ladder," and honestly, that's exactly what the collection of power strings sound similar on this bridge. A climb up the Lord's ladder, a departure from Earth, a one-way trip to anywhere just hither. —Micah Peters

41. "Suspicious Minds," Elvis Presley

Well-nigh heartbreaking line: "We can't continue together / With suspicious minds / And we tin't build our dreams / On suspicious minds"

You can see the ripples of "Suspicious Minds" throughout the grade of breakdown song history, from "Railroad train in Vain" to "Dancing on My Own," which, you know, it'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 Thousand major to very, very E small-scale and merely doesn't ever really resolve. This might non exist the but reason the vocal fades out just in that location'due south no real suitable ending point for the terminal notes of the chorus, so it ever drops dorsum into a poetry or a bridge or another chorus. "John Jacob Jingleheimer Schmidt" resolves more easily. Just similar a broken relationship. —Baumann

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

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

On this archetype Motown tearjerker, Smokey embodies the idea of the sad clown improve than whatever vocal ever has. He's the life of the party—using jokes like a clown uses makeup—but inside, he's wounded, pining for a past lover. He'south dating someone new, but he'due south not thinking of her. (Side notation: I don't know who I'thou sadder for here, Smokey or the rebound he'southward walking effectually town with.) He may take wiped away the tears, simply they've left their mark. And the makeup merely makes the tear tracks that much more than apparent. —Justin Sayles

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

Near heartbreaking line: "So this is inevitable withdrawal / Even if I stop wanting y'all / And perspective pushes through / I'll be some next man's other woman soon"

On "Tears Dry on Their Own," Amy Winehouse demanded that Amy Winehouse take her own advice. "I cannot play myself again, I should only be my own best friend," she warns. "Non fuck myself in the caput with stupid men." These lines that pried the song open were one of Winehouse's hallmarks equally a writer—"Tears" begins in the dumps, in the backwash. Merely 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 terminate being such a dumb, whiny baby. —Peters

38. "Needed Me," Rihanna

Most heartbreaking lines: "Fuck your white horse and a wagon / Bet y'all never could imagine / Never told you you could accept it / You needed me"

This song is so petty and I honey information technology. Rihanna basically made a hit off the "Sike, you idea!" meme and DJ Mustard added an unforgettable beat backside it. This is one of those bangers that you lot and your girls blast postal service-breakup, pre-going-out. Then, later you all sing in unison: "Don't get it twisted / You was just another nigga on the hit list / Tryna gear up your inner issues with a bad bitch," y'all all burst into laughter thinking virtually the man who is now barely a memory. Rihanna's conviction and savageness is really on an untouchable level. (Remember, this song is on the same anthology where she sings "sex with me is so amazing" over and over.) Long may she reign. —Jordan Ligons

37. "So Sick," Ne-Yo

Most heartbreaking line: "Gotta alter my answering motorcar, at present that I'm alone / 'Cause right now it says that we tin't come to the phone"

The earworm of a generation! Ne-Yo said no to sappy ballads in more than ways than ane with "So Sick," giving us an R&B boom striking for anybody sick of regular, schmegular love 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 change my answering machine, now that I'm alone / 'Crusade right at present information technology says that we tin't come up to the phone … Gotta fix that calendar I accept that's marked July 15 / Because since at that place's no more you lot, at that place'due south no more anniversary." Fifteen years afterward, nosotros withal tin can't turn off the radio. —Halliwell

36. "We Vest Together," Mariah Carey

Virtually heartbreaking line: "When you left I lost a office of me / Information technology's still and then hard to believe / Come back infant, please / 'Crusade we belong together"

*Sighs.* This is hands the most played-out, sad breakup song of the early on 2000s. Everyone thought about someone who could've/should've been their soul mate when this dropped in 2005. But now if it comes on the radio and you lot're either happily single or in a solid relationship, your eyes will glaze over, guaranteed. When the get-go ii seconds of the infamous beat come through my speakers, I'1000 already changing the station. It's just and then annoying, and so Mariah.

You may retrieve that you won't find someone else to lean on when times get rough or someone to talk to you on the phone until the dominicus comes upward, but let me tell yous, you volition and y'all'll exist fine. Breakups suck, but please don't torture your broken heart (or your ears) by listening to this vocal on repeat. —Ligons

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

Most heartbreaking line: "Say for me that I'm all correct, though things go kind of wearisome / She might think that I've forgotten her, don't tell her it isn't and so"

The inspiration for Bob Dylan's masterful Claret on the Tracks has always been debated. Critics accept long assumed that the album is about Dylan's separation from his married woman, Sara. The couple's son, Jakob, reportedly believes that Blood is about his parents. But Dylan himself has steadily denied that his masterpiece is autobiographical, even maxim instead that it'due south based on … Chekhov's short stories. "I don't write confessional songs," Dylan told Cameron Crowe during the release of the immersive (and, in the context of this quote, ironically named) Biograph. The truth is, information technology 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 Encounter Her, Say Hullo," which brings us into a fractured relationship in a way that'southward both effortlessly relatable ("We had a falling out, like lovers oftentimes will") and hyper-specific ("And to remember of how she left that night, it withal brings me a arctic"). It'southward not Dylan's flashiest or heaviest or best song, but it is my favorite, a gentle, intimate portrait of lost dear and lasting anguish. Like and then much of his best work, information technology'due south propelled past its poetry, the raw insights nigh how it feels to exist alive. The vocal cycles through the same phases that so many of the states practise while processing heartbreak: deprival, despair, anger, desire. It floats on a electric current of remorse ("Sundown, yellow moon, I replay the past / I know every scene by heart, they all went by and then 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 find / Tell her she tin can look me up, if she'south got the time"). Later on enough listens, and enough heartache of your ain, you realize that "If You See Her, Say Hello" isn't really a breakdown song. It's a dearest letter of the alphabet. — Mallory Rubin

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

About heartbreaking line: "Stand up upward abreast the fireplace / Accept that look from off your confront / 'Cause you own't ever gonna burn my heart out"

The closest I've always come to living in an episode of Glee was when my high schoolhouse French class spontaneously broke out singing "Don't Look Back in Anger." I don't recollect why, just it cemented this song (at least for me) every bit a ballad of communal weltschmerz, rather than personal sadness or regret, similar a fin-de-siècle "You'll Never Walk Alone." (For example: "Don't Look Back in Anger" became a kind of unofficial canticle after the Manchester bombing in 2017.) Oasis knows a affair or two about writing for the communal sing-along, the importance of the languid, memorable tune and the propulsive chord change—this song would carry about the same emotional weight if it were just a title and a chorus. —Baumann

33. "Every Jiff You Take," the Police

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

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

32. "Don't Speak," No Uncertainty

Most heartbreaking line: "Equally we die, both you and I / With my caput in my hands, I sit down and cry"

I hateful, honestly, it takes a lot of guts to drop a Castilian classical guitar solo in the centre of an angsty '90s alt-stone song. Information technology also takes a lot of guts to write a song nearly breaking up with the bass role player in your band and then make a music video for the song that has shots in information technology like the ane below: Don't speak, literally.

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

31. "Thinkin Bout You," Frank Ocean

Most heartbreaking lines: "Practice you lot not think and then far ahead? / 'Cause I been thinkin' bout forever"

Sometimes you have to lie to yourself to get through heartache. They weren't proficient plenty for me. I tin do better. I didn't love them, I just thought they were cute. Frank Sea'south "Thinkin Bout You" exposes that kind of posturing for what it is: a facade. No, I wasn't crying nigh you, and by the manner, I also own waterfront property in Idaho. Frank'south clearly still hung upwards on the past even if his old flame isn't. And the only way to piece of work through the pain is to drop the lying and come make clean with himself. It's tender, information technology'south sugariness, but most of all, it's honest. —Sayles

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

Virtually heartbreaking lines: "Why'd you have to say good day? / Look what you've washed to me / I can't cease these tears from fallin' from my optics"

No matter your current human relationship status, you will for sure sing your heart out when this vocal comes on. I practice not care, I am Mary J. when the chorus hits. By the end of the vocal—a cover of Rose Royce's 1976 single—you've "gone down" 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 be the only one, correct?

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

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

Most heartbreaking lines: "I could put my arms effectually every boy I see / Just they'd only remind me of you"

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

I tin't remember of a vocal that better captures that duality than "Goose egg Compares two U," the 1990 O'Connor hit originally penned by Prince in 1985. Yous can do whatever you desire: Yous tin can party all nighttime, you can eat at a fancy restaurant, you can put your arms around all the boys and girls you'd like, but information technology doesn't matter. It'due south non them, and zip volition be. Your all-time hope is just giving in and living for yourself. —Sayles

28. "Marvin's Room," Drake

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

Drake is at his best when he's subversive because he masks the gaslighting with a softer sadness. "The woman that I would endeavour / Is happy with a proficient 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 anyhow." He proceeds to tell her that the human being she's with isn't adept enough to supplant what they had. Information technology'due south the classic overstep from an ex, but the longer he goes on, we realize it's more about his pride and conflicting emotions about his life choices than information technology is almost her. Drake spirals, telling her he's "had sex iv times this calendar week / I tin can explain," that he'due south sponsoring women, that he tin can't end partying and request for naked pictures. Exactly what your ex-girlfriend wants to hear, I'thousand sure. At least in that location's a voicemail interlude. —Haley O'Shaughnessy

27. "But a Friend," Biz Markie

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

Turns out this adult female did not have what Biz Markie needed. Every bit he singsplains, he became kitten smitten with a adult female at 1 of his shows. Y'all'd think that this would have happened to him all the time, but it did non. This was "the start girl I always talked to," Biz told EW last year. "Every time I would telephone call out to California, a dude would pick up and hand her the phone. I'd be similar, 'Yo, what's upwards [with him]?' She'd say, 'Oh, he'south simply a friend. He's nobody.'" Not taking the hint, Biz flew out to California to surprise her a week before than planned. When he showed up, at that place was a guy "natural language-kissing my girl in her oral cavity."

Biz. My guy. Sit down. Let'due south talk. Start off, she was not your girl. You met her one time. Second, you lot did not catch her tongue-kissing a dude. You stalked her. Tertiary, information technology was extremely obvious that this friend was not just her friend. What Biz Markie needed was someone to listen to his story and give him honest feedback about his predicament. You know, a friend. —Danny Heifetz

26. "Fire," Conductor

Most heartbreaking line: "But yous know, gotta let it go / 'Crusade the political party ain't jumpin' like information technology used to / Fifty-fifty though this might bruise you lot / Let it burn down"

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

All the same, for all of its confusing dorsum-and-forth, this is a breakup classic. It preaches the ideology of forcing yourself to let go even when yous don't know what you're going to practice without your boo. After a heartbreak, everyone has found themselves teetering on the line betwixt regret and freedom. Usher'due south "Burn" allows you to tap into that while simultaneously yelling out, "It's been l-eleven days, umpteen hours, and Imma exist burnin' till you lot return!" —Ligons

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

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

If you're e'er at your wits' end, tragically obsessed with someone who treats you similar shit, you can find some catharsis in the controlled chaos of Janis Joplin's song performance on "Piece of My Heart." Go ahead and scream along. Y'all won't sound every bit adept as Janis, but yous'll certainly feel a hell of a lot better afterward.

Once your anger fades a lilliputian, you can switch over to the original recording of this song, released a yr earlier in 1967 and sung by Erma Franklin (yes, that'south Aretha'due south older sister). Or if you need some more twang accompanying your despair, y'all can effort the Faith Hill version. I besides won't judge you if the only person who can ease your hurting is Shaggy (or Beverley Knight, Melissa Etheridge, Steven Tyler, Kelly Clarkson, or one of endless other artists).

Written by Jerry Ragovoy and Bert Berns, "Piece of My Centre" is one of the most relatable and indelible 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 sharp, primal weep. Undoubtedly, there will be new versions of this song until the end of time⁠—because it'due south an accented banger—but too considering … men. —Matt James

24. "Skinny Honey," Bon Iver

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

A good dominion for breakup songs is that there has to be a office that you can yell forth to, unencumbered by silly things like constraint and self-awareness. The chorus of Bon Iver's "Skinny Love" has a slap-up ane, especially for anyone who'south merely exited a relationship and feels compelled to heap all the blame on the other political party.

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

23. "Hold Up," Beyoncé

Well-nigh heartbreaking line: "Tin't you lot run across there's no other homo higher up you? / What a wicked fashion to treat the girl that loves y'all"

It'due south hard to express existent hurt over an uptempo crush and make the heartbreak convincing. Yet Beyoncé is conceivable in "Concord Up," a painful accounting of the emotions that come after discovering that your partner has cheated. Lemonade was inspired by true events—i.due east., information technology'south Beyoncé coming to terms with Jay-Z existence unfaithful. Infidelity brings on a very specific type of destruction: You're mad; you're miserable; you lot're humiliated. You switch from one emotion to another in a matter of minutes. She opens the song with confidence: No other woman tin give what she tin can. "Concur up, they don't beloved you like I love you." In a breath, she's less certain of herself: "What'south worse, looking jealous or crazy?" Beyoncé settles on crazy, then returns to anger. "Y'all let this skillful dearest go to waste." —O'Shaughnessy

22. "Weep Me a River," Justin Timberlake

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

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

In his offset solo megahit, Justin insinuates his love has cheated on him ("You don't take to say what you did / I already know, I constitute out from him") and writes her off for proficient. He'southward already cried well-nigh it, and now it'due south her turn. But no amount of her tears can disengage the harm; he'south gone. You didn't take to do much sleuthing to figure out he was singing about Britney. That celebrity intrigue, Timbaland'south sharp production, and an instantly memorable music video combined to brand "Cry Me a River" the most iconic breakdown vocal of the early 2000s, catapulting him to another level of stardom. He had split with non just Britney, but also his past, and he was fix for the globe. —Sayles

21. "With or Without You," U2

Most heartbreaking line: "She got me with goose egg to win / And zippo left to lose"

Nothing changes if cypher changes, equally they say, and "With or Without You" exists in that hopelessly recursive "I hate that I love you" space. This song was U2'due south first no. ane hit in the U.S., even though, Bono has said, "it's a very odd-sounding song … it kind of whispers its mode into the earth." Only information technology's not the whispers that resonate most, however, it'due south all those wails, like the crescendo of Bono's agonized, eminently singalong-able ahhh-ahhh-ahh-ahhhhhs, or the painful, everlasting notes from the Border's "infinite guitar," engineered to hold a tone as if information technology were a grudge. "Psychotic restraint" is how Bono characterized the Edge's spare work on this track, a description that could double every bit breakup advice. —Katie Baker

20. "Jolene," Dolly Parton

Virtually heartbreaking line: "And I tin easily understand / How you could hands have my man / But y'all don't know what he means to me, Jolene"

While other female country singers might've handled their man's newfound fascination with a beautiful redhead by, say, digging a key into the side of his pretty fiddling souped-up four-cycle drive, or—just spitballing here—threatening to ship her to Fist Metropolis, Parton merely pleads for mercy. The desperate pitch of her entreatment, set against a frantic Dorian-fashion guitar riff, sets the stakes far higher than those you might discover in generally stern country songs near cheatin', lyin', and beingness untrue. Any armchair scholar of Parton'south piece of work can tell you lot she cloaks feminist manifestos within marketable diddies about everyday experiences. I've always taken the song's urgency to imply something that every woman learns eventually: Relationships can be both romantically fulfilling, and, too often, 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 Information technology Through the Grapevine," Marvin Gaye

Most heartbreaking line: "Do y'all plan to let 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 information technology on his album In the Groove. Perhaps the song resonated with Gaye because he married a 41-year-erstwhile woman when he was just 24, and their matrimony was total of infidelities. "I was in love with the idea of love," Gaye once said. Or at least that's what I heard through the grapevine. —Heifetz

eighteen. "Ex-Gene," Lauryn Colina

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

"Ex-Factor" is more than a breakup song, it's nigh recognizing a toxic relationship before y'all have the words to call information technology 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 human relationship on the rocks: the hurting, the complicity, and the unwillingness to give upwardly on a love you think is still there, buried below the bullshit.

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

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

Most heartbreaking line: "Well, yous said that we fabricated such a pretty pair / And that you would never go out / Just yous gave abroad the things yous loved / And one of them was me"

Far earlier Taylor Swift sent her fans on subtweet scavenger hunts, Carly Simon penned a ballsy kissoff that, cheers to its self-referential chorus, left the world wondering whom it was about and what they could've perchance done to acrimony her. More 40 years of speculation later, we now know that the singer was describing the actor Warren Beatty. (She added in a contempo, withering interview that, although the song describes three separate men, Beatty "thinks the whole thing is about him.") We may never know what company he kept (coughing: Mick Jagger?), but the lasting power of Simon's clear-eyed takedown stands as a referendum on the unchecked male ego, whether its independent in the torso of a dashing histrion or a moody fuckboy. —Bereznak

xvi. "Dancing on My Own," Robyn

About heartbreaking line: "Aye, I know it's stupid, I merely gotta meet it for myself"

Last year, following a Robyn show at Madison Square Garden, elated concertgoers connected the party on the A/C/Eastward railroad train subway platform, breaking into a featherbrained public performance of "Dancing on My Own." Y'all wouldn't typically await a breakup song to be the one that leads New Yorkers to such displays of collective joy, only most breakup songs aren't similar this one: a vocal yous can strut to, a club anthem, a scene-stealer, a story of lonesomeness that still finds its solace in a crowd. Information technology'south a song about moving on—I just came to say good day—but too well-nigh, merely, moving. The singer might be solitary in the corner, and she might know it's stupid, but she'south out in that location dancing, at to the lowest degree. —Bakery

15. "Thank U, Next," Ariana Grande

Almost heartbreaking line: "Wish I could say, 'Thank y'all' to Malcolm / 'Crusade he was an angel"

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

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

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

About heartbreaking line: "Information technology'south unnatural"

Both the joyous genesis and abject death knell for billions of '90s inferior-high-gymnasium-dance relationships that just lasted the length of the song itself, "Terminate of the Route," which rose to ability on 1992'south Boomerang soundtrack, is one of the biggest hits in pop-music history. Like, "13 direct weeks atop the Hot 100" big. Like, "The 'Old Town Road' of Its Day" big, a tearjerking shout-forth canticle 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's unnatural / You lot belong to me / I belong to you lot." The discussion unnatural has never sounded so natural, and then miserable. —Harvilla

13. "Dreams," Fleetwood Mac

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

Even xl-plus years on, to hear Stevie Nicks softly moaning, "What y'all had ... and what you lost / And what you lot 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 2nd (and all-time!) track on 1977's zillions-selling Rumours, "Dreams" is both radically overexposed and still somehow criminally underrated, fixed to its iconic identify, fourth dimension, and circumstances but as well shockingly timeless. (Zoë Kravitz rhapsodizes it in the airplane pilot of Hulu'south new High Allegiance remake serial to prove her stone-nerd bona fides.) Pair it with "Silverish Springs" for maximum result. —Harvilla

12. "How Can You Mend a Broken Middle," Al Greenish

Most heartbreaking line: "Let me live again"

At that place'southward heartbreak, and then at that place's Al Greenish heartbreak. (Non to slight the original Bee Gees version—Green is all I know when I'chiliad going through it.) He's exasperated from the beginning, wondering whether he'll ever recover from the love that went away. The agony is plenty to contemplate nature itself in the chorus: "How tin can you mend a broken heart? / How can yous end the rain from falling downward? / How can you stop the sun from shining? / What makes the world go round?" Greenish is begging for answers, for "somebody, please" to come fix him. He pleads, "Let me live again." Life as he knew it is over without this person, and as long as the song is on, it feels over for us, as well. —O'Shaughnessy

xi. "Torn," Natalie Imbruglia

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

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

10. "I Will Survive," Gloria Gaynor

Most heartbreaking line: "And and then y'all felt like dropping in and just expect me to be free / Well now I'm saving all my lovin' for someone who's lovin' me"

This 1978 disco colossus is so singular, and so monolithic, so wedding ceremony-dancefloor-ingrained that information technology hardly scans as a breakup song at all: As ecstatic and empowering fuck-you anthems become, it is the glamorous grandmother to Lizzo's "Truth Hurts" and Ariana Grande's "Thank U, Next" and Beyoncé'due south "Irreplaceable" and roughly l,000 other self-affirming pop hits. What truly elevates New Bailiwick of jersey diva Gloria Gaynor's all-timer, though, is its sociopolitical import: "I Will Survive" has long been a stirring battle hymn for the LGBTQ customs, for survivors of domestic violence, for anyone who can relate in whatever fashion, frivolously or otherwise, to the bluntly iconic line "I'm saving all my lovin' for someone who's lovin' me," which of class is everybody. She knows you're afraid; she knows you lot're petrified. Simply she as well knows you won't stay that style for long. —Harvilla

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

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

To make a song from 1971 nigh a video game from 2010: Dante's Inferno is an RPG based loosely on the first canticle of the Divine Comedy. I say loosely because EA Dante has rippling muscles and a massive scythe, his only protections confronting the legions of the night, who've stolen his love Beatrice. I never played it, merely a friend who did described his frustration with the game: It's equally if its conclusion got further away the more time he devoted to it. A Super Bowl commercial showed Dante sprinting toward Hell'due south gaping oral fissure determined but, you know, definitely doomed. As he descends you lot hear the low croak of Nib Withers's vocalisation, pining after a lost lover: "Ain't no sunshine when she's gone, only darkness everyday." My last breakdown didn't involve a behemothic flaming devil monster, but information technology did feel like a similarly hopeless uphill battle. —Peters

eight. "Someone Like You," Adele

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

The queen of heartbreak has never been improve than on sophomore album 21, and 21 doesn't get much better than "Someone Like You." Adele'southward ode to the i who got abroad is perhaps the most universally adored tearjerker of the past decade; starting with that uncomplicated pianoforte line and ending in that crushing hook: "Sometimes it lasts in love, but sometimes information technology hurts instead." And of course, that voice! Watching the unproblematic blackness 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 all-time for her ex ("One-time friend, why are you so shy?"), merely damn, she's notwithstanding pain. Aren't we all! —Halliwell

seven. "I Want Yous Dorsum," The Jackson 5

Most heartbreaking lyrics: "Someone picked you from the bunch, one glance was all information technology took / Now it's much too belatedly for me to accept a 2d look"

Perhaps the almost outwardly joyous song in this entire ranking, "I Want You lot Dorsum" spins a tale that anyone who'due south ever taken someone for granted will understand. An 11-twelvemonth-quondam Michael Jackson is at his most precocious here, singing about the girl whom he didn't fully appreciate until someone else stole her heart. Now he but wants another chance to show that he knows how to treat her correct. Michael, of course, didn't write the song—it was penned by Berry Gordy and Co.—but he sells information technology in a style that someone two or iii times his historic period never could. A leopard tin't change its spots, just if it sounds this skilful trying to convince you it tin can, why not give it i more gamble? —Sayles

6. "Since U Been Gone," Kelly Clarkson

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

There is a moment in every breakup where, afterwards a few weeks of self-compassion, y'all shed your sweatpant cocoon, step outside, and, with the instantaneity of a rubber ring snap, of a sudden know deep within your eye that your ex was an detestable blowhard. Kelly Clarkson's mosh-adjacent ability pop carol embodies the newfound self-assurance that comes with that realization. Information technology also happens to be enshrined in a popular civilisation moment that I volition forever associate with being a melodramatic 16-year-old millennial: "Since U Been Gone" was written past pop lords Max Martin and Dr. Luke, who ripped its entire musical structure from the far more poetic Yeah Yes Yeahs hitting, "Maps," and then—after being passed up by both Pinkish and Hilary Duff—was sung by the very first winner of the so-fledgling reality TV show American Idol. The AIM-friendly "U" in the title is just the icing on the block. —Bereznak

5. "Ms. Jackson," Outkast

Most heartbreaking lyric: "Forever never seems that long until you lot're grown / And notice that the mean solar day-by-day ruler can't be too wrong"

Sometimes breaking up with your meaning other'due south family is merely as difficult as breaking up with them. Big Boi and André 3000 understood that on "Ms. Jackson," a vocal dedicated to Kolleen Maria Wright, the mother of Erykah Badu, with whom André had a child. Three Stacks's verse is specially poignant—his intentions were good, but things took a plough for the worse. Information technology'south a harsh reality: Well-nigh relationships are born with an expiration date, no affair how bright the flame burned at the beginning. As far as amends songs go, it's pretty nuanced and sincere. And Wright seems to have bought it: Erykah said in 2016 that her mother even has a "MSJACKSON" license plate. —Sayles

four. "I Volition Ever Love Yous," Whitney Houston

Well-nigh heartbreaking line: "Please don't weep / We both know I'm non what you, yous need"

Dolly Parton wrote one of the most dynamic love songs e'er with "I Will E'er Dear Yous." Whitney Houston, who sang a comprehend for the movie The Bodyguard, made a worldwide hit with her astounding range. Both versions are wonderful for unlike reasons, though Parton's honeyed, wobbly original is best for heartbreak. For one, it's authentic: She wrote the song for her onetime manager and professional person partner, Porter Wagoner, later on she decided to leave him. Parton is sympathetic, yet determined to go. As she sings in the span, it'due south bloodshot. They are both meliorate off this fashion, she argues, simply wishes him nothing only "joy and happiness." One of the hardest relationship lessons is that 2 people can dear each other and it still not be correct for either—thanks to Dolly and Whitney, it was 1 learned early on. —O'Shaughnessy

3. "I Can't Brand You Beloved Me," Bonnie Raitt

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

You might be a girlfriend, a husband, a partner, or even a friend with benefits. Whatever part you play in service of beloved, 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 love lives is that love itself can be a ruthlessly nonbinding agreement, an at-will organisation. Even more frightening is that it's oft our hearts—not us—calling the shots.

What sets "I Can't Make You Beloved Me" apart from nigh breakup songs is that information technology takes identify at the about painful point of a breakdown: credence. It's not a post-breakup anthem of empowerment or a drastic plea to stay together. It's the full forcefulness of the disorienting one-two punch of loss and loneliness. It'south the globe-shattering moment when you give upwardly the fight.

Bonnie Raitt'due south arresting performance of this vocal (written by Mike Reid and Allen Shamblin) carries the weight of a lifetime in and out of love. She sets down her slide guitar, sits Bruce Hornsby down at the piano, and sings the absolute fuck out of this song with conviction and grace. The vocal used on the Luck of the Depict anthology recording was Bonnie's outset take. "I Can't Make You lot Love 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 near deeply are the ones that unite us through the nearly homo of shared experiences. Eventually, we all larn that you can't brand someone'south heart feel "something information technology won't." Merely should y'all one day notice yourself at rock bottom, suddenly solitary in darkness—whether it'due south your first time or your 14th—you lot can feel a little fleck less solitary knowing that Bonnie's been there, likewise. —James

2. "You lot Oughta Know," Alanis Morissette

Most heartbreaking line: "Does she know how yous told me you lot'd hold me until you died, till you died / But you're still alive"

Alanis Morrisette was nineteen years former when she recorded that ballad of bitterness "You Oughta Know" in one accept at 11 p.m. "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 Little 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 information technology was possibly inspired by Uncle Joey remains both iconic and securely weird, only also makes sick sense: You haven't truly been jilted until you've been jilted by someone who'due south not even that cool, you know?) "You Oughta Know" totally scandalized my mom every time information technology 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 could yous want—other than sweet, sweet vengeance? —Baker

one. "Purple Rain," Prince

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

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

Some breakup songs are hateful, some are mournful, others are empowering. Just "Purple Rain" has the ability to experience like everything all at once, a near-religious experience of a song 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

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