Know Your Tired of Heartbreaks but Baby I Am Not Them

What makes a song a "breakup song"? Does it have to be empowering, à la "I Will Survive" or nearly of the songs on Lemonade? Should it be for the solitary, like Carole King's "It'southward Also Late" or Bob Dylan'south "If You lot Run across Her, Say Hello"? Does it take to accost the breakup in the lyrics? (Taylor Swift has many entrants in this category, and Marvin Gaye penned an entire album nigh his divorce.) What about songs with a famous backstory, like "Cry Me a River" or any rail off of Rumours?

Nosotros here at The Ringer believe that since heartache comes in many forms, so should the breakup song. And in laurels of Valentine's Day, we decided to dig deep into the genre. Below, you'll discover our ranking of the 50 greatest breakup songs of all time, as voted on past our staff. The list spans several decades and many different moods, merely all are rooted in some type of pain. There was only i dominion for the final ranking: just i song per artist was included to avert Dolly Parton or even Drake from dominating.

So if you're lonely, fire upward our playlist and cry forth as you read our thoughts on each entrant. If you're happily attached, you tin can however dive in—these are some of the greatest songs always recorded, and that's true whether y'all're in your feelings or not. Maybe you'll gain a greater appreciation for your current relationship. After all, breakup songs resonate but when you know what it's like to lose in dear. —Justin Sayles

50. "We Are Never E'er Getting Back Together," Taylor Swift

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

One of the virtually cruel breakup songs in history, "Nosotros Are Never Always Getting Back Together" encapsulates the severe "fuck that guy!" energy that follows a long-overdue parting of ways. We've all had that postal service-fight bluster with our friends: "Ugh … and so he calls me up and he'southward like, 'I yet dearest y'all,' and I'g similar … 'I just … I hateful this is exhausting, you know, like, we are never getting back together. Like, ever.'" Brassy, triumphant, and entirely wearied past All Men, Taylor Swift gave us the perfect soundtrack for breakup recovery. — Kate Halliwell

49. "I Miss You," Glimmer-182

Most heartbreaking line: "I demand somebody and ever / This sick foreign darkness / Comes creeping on so haunting every time"

"I Miss You" is like a minimalist/emo take on Meat Loaf. It rules. The two best things about this number are Travis Barker's simple but persistent drumbeat and Tom DeLonge's entrance on the 2nd verse. Information technology's role of the thou pop punk tradition of showing y'all mean business past going up an octave, of which "I Miss Yous" (forth with the Starting Line's "The All-time of Me") is the exemplar.

Don't just have my discussion for it, though. Consider Grammy-winning producer Finneas's take: "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'due south Also Belatedly," Carole King

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

"Information technology'southward Too Belatedly" is a crushing ode to the most mutual kind of breakup. The natural process of 2 people growing apart is equally heartbreaking as it is commonplace, and King sings in a tone perfectly situated betwixt her sorrow and the shrugging access that "nosotros really did try to go far." Her conversational delivery early in the song brings us into the living room, diner, or sidewalk where "the talk" between her and her about-to-be-ex is happening: "One of usa is changing, or maybe nosotros just stopped trying," she sings, plainly laying out the central, blameless reasons for why near people end upwards separating. The song is defined by its maturity and its conciliatory attitude, but as with actual breakup conversations, that doesn't make it any easier to hear. —Cory McConnell

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

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

This is a perfect example of the kind of breakup song you lot hear on the radio (or, in the late '90s, possibly the social club—the Frankie Duke house remix nevertheless goes) and, on a normal day, simply hear some other pop song, merely when you're experiencing heartache, what originally sounded like songwriting clichés become the truest words you've always heard. "I have cried a lot of nights," you think, getting out of bed for the showtime time in days to grab a scroll of toilet paper since you ran out of Kleenex. "Life is cruel without you here abreast me," you murmur, staring into the bleak chasm of loneliness you now know as life. "I would literally do anything on God's greenish earth to hear y'all say you honey me once again," you realize with the greatest clarity you lot've ever experienced. Anyway, where are my altos at? This is our karaoke song. — Kjerstin Johnson

46. "Mr. Brightside," the Killers

Most heartbreaking line: "At present they're going to bed and my stomach is sick / And information technology's all in my head"

Maybe information technology's not exactly right 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-actually-started-cheating-on-me song. Just that'southward all really clunky, and then let's accept being slightly incorrect for the sake of cleanliness. Either way, "Mr. Brightside" is an iconic mid-aughts vocal that's perfect for yell-karaoking and that pulls off the difficult fox of just repeating 1 verse over and over. Too, Eric Roberts in the video. —Andrew Gruttadaro

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

Most heartbreaking line: "Become upward 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 rise to greatness begins here, with the breakout hitting from their 2nd album, 1973's oddly/heartbreakingly named Abandoned Luncheonette. "She'due south Gone" is luscious and silky and deceptively lite, all Motown grandeur by manner of blue-eyed Philly soul, but that lightness only underscores the exquisite heaviness of murmured poesy lines like "Get up in the morning, look in the mirror / Worn as the toothbrush hanging in the stand up." (Or probably it'southward "One less toothbrush," which of grade is fifty-fifty heavier.) The chorus, by contrast, is gigantic and regal and crushing, punctuated by cloudbursting lamentations of "She'southward gone! / Oh why? / Oh why?" The boys merely got bigger from here, merely they certainly never got sadder. —Rob Harvilla

44. "Tyrone," Erykah Badu

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

The second-best moment on this viciously sultry tedious jam, the crown gem of Erykah Badu's 1997 album Live, is the stupendous opening line: "I'one thousand gettin' tired of your shit / Y'all don't ever buy me nothin'." The kickoff-best moment is all the women in the crowd immediately shrieking with please and, one fears, recognition. "Tyrone" is named for one of an unnamed deadbeat lover'southward numerous deadbeat friends: "Every fourth dimension we go somewhere," Badu purrs with lethal authorization, "I gotta reach down in my purse / To pay your way and your homeboy's way and sometimes your cousin's fashion." It is the gender-flipped riposte to Friday's "Adieu, Felicia," and in fact turned up as a joke in 2000'south Next Friday; it "followed me thru my career similar an obsessed X boyfriend," as Badu put it on Instagram in 2017, while shouting out her backup singers, whose sardonic and sublime "Call him!" chant is the 3rd-best moment. —Harvilla

43. "Honey Is a Battleground," Pat Benatar

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

The agonizingly propulsive signature hit from flamethrower-voiced '80s pop queen Pat Benatar laments non so much a breakup as a nigh-breakdown in progress, an acknowledgement that truthful honey means almost breaking up pretty much all the fourth dimension: "Believe me / Believe me / I can't tell you why / Just I'm trapped by your love / And I'm chained to your side." Information technology'south a karaoke classic you have no business organisation attempting, a cheeseball Reagan-era nail of eternal profundity, and a striking annunciation that sometimes the only affair worse than splitting up is non splitting up: "Do I stand up in your way / Or am I the best thing yous've had?" she wails with 18-carat desperation, and the answer, of course, is both. —Harvilla

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

Most heartbreaking line: "Throwing shit effectually, the whole identify screwed upwardly / Mayhap I should call Mase so that he could pray for united states"

Nosotros're not even talking about the whole song—nosotros're talking most xx or so seconds of Bink production afterwards Kanye'southward second verse, but before Rick Ross'southward only verse, arguably 1 of the best in his career. In it, he describes Due west'due south near-fatal machine crash in 2002 as an aborted climb "upwardly the Lord's ladder," and honestly, that'southward exactly what the collection of power strings sound similar on this bridge. A climb up the Lord'due south ladder, a departure from Earth, a one-way trip to anywhere but hither. —Micah Peters

41. "Suspicious Minds," Elvis Presley

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

Yous can see the ripples of "Suspicious Minds" throughout the course of breakup song history, from "Train in Vain" to "Dancing on My Ain," which, you know, it's Elvis. Only beyond the juxtaposition of its relatively upbeat music and depressing-as-hell lyrics, I dear the construction of this song, with a peppy guitar intro and verses that build into a chorus that goes from G major to very, very E minor and just doesn't always really resolve. This might not be the but reason the vocal fades out just there's no real suitable ending point for the terminal notes of the chorus, so information technology always drops back into a verse or a bridge or another chorus. "John Jacob Jingleheimer Schmidt" resolves more easily. Just like a cleaved relationship. —Baumann

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

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

On this classic Motown tearjerker, Smokey embodies the idea of the sad clown better than any song always has. He'due south the life of the political party—using jokes like a clown uses makeup—but within, he's 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'south walking effectually boondocks with.) He may accept wiped away the tears, but they've left their marker. And the makeup only makes the tear tracks that much more credible. —Justin Sayles

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

Most heartbreaking line: "So this is inevitable withdrawal / Even if I stop wanting you lot / And perspective pushes through / I'll be some next human being's other woman shortly"

On "Tears Dry on Their Own," Amy Winehouse demanded that Amy Winehouse take her own advice. "I cannot play myself again, I should merely be my own all-time friend," she warns. "Not fuck myself in the caput with stupid men." These lines that pried the song open were one of Winehouse'due south hallmarks as a writer—"Tears" begins in the dumps, in the backwash. Only during every emotional uncoupling comes the point where you gaze into the mirror, stick your finger in your reflection's chest, and tell them to stop existence such a dumb, whiny baby. —Peters

38. "Needed Me," Rihanna

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

This vocal is so petty and I love it. Rihanna basically fabricated a hit off the "Sike, you thought!" meme and DJ Mustard added an unforgettable beat behind it. This is 1 of those bangers that you and your girls nail post-breakup, pre-going-out. Then, later on you all sing in unison: "Don't get it twisted / You was just some other nigga on the striking list / Tryna fix your inner issues with a bad bowwow," you all burst into laughter thinking most the human who is at present barely a retention. Rihanna'due south conviction and savageness is really on an untouchable level. (Remember, this vocal is on the same album where she sings "sex with me is then amazing" over and over.) Long may she reign. —Jordan Ligons

37. "Then Ill," Ne-Yo

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

The earworm of a generation! Ne-Yo said no to sappy ballads in more than ways than one with "So Ill," giving united states of america an R&B smash striking for everyone ill of regular, schmegular love songs. Prepare to the globe's catchiest crush, Ne-Yo mourns a past relationship and all the twenty-four hours-to-day changes that come with moving on. "Gotta alter my answering machine, now that I'g solitary / 'Crusade right now it says that we can't come up to the phone … Gotta prepare that calendar I accept that's marked July xv / Because since there's no more you lot, in that location'due south no more anniversary." Fifteen years subsequently, nosotros still can't turn off the radio. —Halliwell

36. "Nosotros Belong Together," Mariah Carey

Nearly heartbreaking line: "When you left I lost a part of me / It'southward still so hard to believe / Come dorsum baby, please / 'Crusade we vest together"

*Sighs.* This is hands the well-nigh played-out, sad breakup song of the early 2000s. Everyone thought about someone who could've/should've been their soul mate when this dropped in 2005. Merely now if it comes on the radio and you're either happily unmarried or in a solid human relationship, your eyes will glaze over, guaranteed. When the first ii seconds of the infamous beat come up through my speakers, I'm already irresolute the station. Information technology'south just so annoying, and and so Mariah.

Yous may think that you won't detect someone else to lean on when times get rough or someone to talk to you on the phone until the sun comes up, but let me tell yous, you volition and you lot'll be fine. Breakups suck, but please don't torture your cleaved eye (or your ears) by listening to this vocal on repeat. —Ligons

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

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

The inspiration for Bob Dylan'south masterful Blood on the Tracks has always been debated. Critics have long assumed that the album is virtually Dylan's separation from his wife, Sara. The couple's son, Jakob, reportedly believes that Blood is about his parents. But Dylan himself has steadily denied that his masterpiece is autobiographical, even saying instead that information technology's based on … Chekhov'south curt 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 one time deeply personal and universal.

That's most palpable on "If You Run into Her, Say Howdy," which brings united states of america into a fractured relationship in a fashion that'southward both effortlessly relatable ("We had a falling out, like lovers ofttimes volition") and hyper-specific ("And to recollect of how she left that night, it notwithstanding brings me a chill"). It's not Dylan's flashiest or heaviest or best vocal, only it is my favorite, a gentle, intimate portrait of lost dearest and lasting ache. Like so much of his best work, it'southward propelled past its poetry, the raw insights about how information technology feels to be live. The song cycles through the aforementioned phases that so many of united states practise while processing heartbreak: denial, despair, anger, desire. It floats on a current of remorse ("Sundown, yellowish moon, I replay the past / I know every scene by heart, they all went by so fast") yet manages to convey the kind of longing that leads, charily, back toward hope ("If she'southward passing back this way, I'm not that difficult to observe / Tell her she can wait me upwards, if she's got the time"). Later plenty listens, and enough heartache of your own, you realize that "If You Encounter Her, Say Hello" isn't really a breakdown song. It'south a love alphabetic character. — Mallory Rubin

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

Nigh heartbreaking line: "Stand up upwards beside the fireplace / Take that await from off your confront / 'Crusade you own't ever gonna burn my center out"

The closest I've ever come to living in an episode of Glee was when my loftier schoolhouse French class spontaneously broke out singing "Don't Look Back in Anger." I don't recall why, simply information technology cemented this song (at least for me) as a ballad of communal weltschmerz, rather than personal sadness or regret, like a fin-de-siècle "Y'all'll Never Walk Lone." (For instance: "Don't Look Back in Anger" became a kind of unofficial anthem after the Manchester bombing in 2017.) Oasis knows a matter or two about writing for the communal sing-forth, the importance of the languid, memorable melody and the propulsive chord change—this song would carry nigh the same emotional weight if it were just a title and a chorus. —Baumann

33. "Every Breath You Take," the Police

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

This spectacularly maudlin New Wave ballad, which anchored the Law's 1983 goliath Synchronicity and reigned every bit one of the biggest radio hits of the decade, is creepy as all hell, very much by blueprint: an unrepentant stalker manifesto that doesn't so much describe spurned beloved in terms of surveillance as it describes total state surveillance in terms of spurned love: "Every move you lot brand / Every vow you lot break / Every smile you simulated / Every claim you stake." And so on. "I'll be watching you lot," Sting concludes a couple dozen times throughout, but information technology's the chest-pounding bridge where the trio's creepy-soulful frontman does some of his best belting, his best pleading, his best super-creepy emoting and enunciating: "I feel so cold and I long for your em-brace." Fun fact: He started writing the song at Ian Fleming's writing desk on the James Bail author's luxe Jamaican estate, which might non exist creepy, but it'due south certainly weird. —Harvilla

32. "Don't Speak," No Doubt

About heartbreaking line: "As we die, both yous and I / With my caput in my hands, I sit down and cry"

I mean, honestly, information technology takes a lot of guts to driblet 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 vocal nearly breaking upwardly with the bass player in your band and and so brand a music video for the song that has shots in it like the one below: Don't speak, literally.

No Dubiousness's first hit is a work of art, total of raw, youthful emotion and complex arrangements. It'due south beautiful, savage, painful, and incendiary, all at once. —Gruttadaro

31. "Thinkin Bout You," Frank Ocean

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

Sometimes you have to lie to yourself to go through heartache. They weren't good enough for me. I can do better. I didn't dear them, I but thought they were cute. Frank Sea'south "Thinkin Bout Y'all" exposes that kind of posturing for what information technology is: a facade. No, I wasn't crying about you, and by the way, I also own waterfront property in Idaho. Frank'due south clearly however hung upwards on the past even if his erstwhile flame isn't. And the only way to work through the pain is to drop the lying and come up clean with himself. It's tender, information technology's sweet, but most of all, it's honest. —Sayles

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

Well-nigh heartbreaking lines: "Why'd yous have to say goodbye? / Look what you've done to me / I tin't stop these tears from fallin' from my eyes"

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

Also, remember when Tamera sang this vocal for the talent bear witness on Sister, Sis? Iconic. —Ligons

29. "Null Compares ii U," Sinéad O'Connor

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

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

I can't call back of a song that improve captures that duality than "Nothing Compares ii U," the 1990 O'Connor hit originally penned past Prince in 1985. You can do whatever yous want: Y'all tin party all night, y'all can swallow at a fancy restaurant, you can put your arms around all the boys and girls you lot'd similar, simply information technology doesn't matter. It'south not them, and nil volition exist. Your best promise is just giving in and living for yourself. —Sayles

28. "Marvin'south Room," Drake

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

Drake is at his best when he'due south subversive because he masks the gaslighting with a softer sadness. "The woman that I would endeavor / Is happy with a good guy," he sings. Is he happy for her? The lines suggest that there'south at least a take a chance. Drake pauses, so goes total Drizzy Deleterious: "But I've been drinkin' so much / That I'ma telephone call her anyhow." He proceeds to tell her that the man she's with isn't good plenty to replace what they had. Information technology's the classic overstep from an ex, just the longer he goes on, we realize it'south more about his pride and conflicting emotions about his life choices than it is almost her. Drake spirals, telling her he'south "had sex activity iv times this calendar week / I can explain," that he'due south sponsoring women, that he tin can't stop partying and asking for naked pictures. Exactly what your ex-girlfriend wants to hear, I'yard certain. At least there'south a voicemail interlude. —Haley O'Shaughnessy

27. "Simply a Friend," Biz Markie

Nigh heartbreaking line: "Oh, snap! Gauge what I saw? / A fella natural language-kissin' my daughter 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 i of his shows. You'd call back that this would have happened to him all the time, but it did not. This was "the outset girl I ever talked to," Biz told EW last yr. "Every fourth dimension I would call out to California, a dude would selection upwards and hand her the phone. I'd be like, 'Yo, what's up [with him]?' She'd say, 'Oh, he'due south just 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, there was a guy "tongue-kissing my girl in her mouth."

Biz. My guy. Sit down. Permit'due south talk. First off, she was non your girl. Yous met her i time. Second, yous did not catch her tongue-kissing a dude. You stalked her. 3rd, it 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 well-nigh his predicament. You know, a friend. —Danny Heifetz

26. "Burn," Usher

Most heartbreaking line: "Just you know, gotta let it go / 'Cause the party ain't jumpin' similar it used to / Fifty-fifty though this might bruise yous / Permit it burn"

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, simply our human relationship has to come up to an end; he says he's hurting and he's non happy, but he's breaking down and crying. Deep down he knows information technology's best, but he hates the thought of me being with someone else. Get your shit together, Usher!

Still, for all of its confusing back-and-forth, this is a breakup classic. Information technology preaches the ideology of forcing yourself to let go even when you don't know what yous're going to do without your boo. After a heartbreak, everyone has found themselves teetering on the line between regret and freedom. Usher'southward "Burn" allows you to tap into that while simultaneously yelling out, "Information technology's been 50-eleven days, umpteen hours, and Imma be burnin' till you return!" —Ligons

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

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

If you're ever at your wits' end, tragically obsessed with someone who treats you similar shit, you tin can discover some catharsis in the controlled chaos of Janis Joplin's vocal functioning on "Piece of My Heart." Go ahead and scream forth. You won't audio every bit good as Janis, but yous'll certainly feel a hell of a lot meliorate afterward.

Once your anger fades a little, you can switch over to the original recording of this song, released a year earlier in 1967 and sung by Erma Franklin (yes, that'southward Aretha's older sis). Or if you lot demand some more twang accompanying your despair, you tin endeavor the Faith Hill version. I as well won't judge you lot if the but person who can ease your pain is Shaggy (or Beverley Knight, Melissa Etheridge, Steven Tyler, Kelly Clarkson, or i of countless other artists).

Written by Jerry Ragovoy and Bert Berns, "Slice of My Centre" is one 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 abrupt, primal cry. Undoubtedly, there volition be new versions of this vocal until the terminate of time⁠—because it'southward an absolute banger—but also considering … men. —Matt James

24. "Skinny Love," Bon Iver

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

A good rule for breakup songs is that there has to exist a part that you lot can yell along to, unencumbered past airheaded things like constraint and self-awareness. The chorus of Bon Iver's "Skinny Love" has a great one, especially for anyone who'south simply exited a relationship and feels compelled to heap all the blame on the other party.

You know the story by now: In 2006, Justin Vernon broke up with his girlfriend, packed upwards his car, and drove into the Wisconsin wilderness, emerging but afterward recording an album of weepy breakup songs. That origin tale has been repeated then frequently that information technology's become soft mush, obscuring the real truth: That For Emma, Forever Ago—and particularly "Skinny Dearest"—are profoundly reflective, intelligent, moving documents about the breakdown of a human relationship. —Gruttadaro

23. "Hold Upwardly," Beyoncé

Nearly heartbreaking line: "Tin can't you see there's no other man above you? / What a wicked manner to treat the daughter that loves you"

Information technology'south hard to express real hurt over an uptempo crush and make the heartbreak convincing. Yet Beyoncé is believable in "Agree Up," a painful accounting of the emotions that come afterwards discovering that your partner has cheated. Lemonade was inspired by true events—i.e., information technology's Beyoncé coming to terms with Jay-Z being unfaithful. Adultery brings on a very specific type of destruction: Yous're mad; you're miserable; yous're humiliated. Yous switch from i emotion to another in a matter of minutes. She opens the vocal with conviction: No other woman tin can give what she can. "Hold up, they don't dearest you similar I love you." In a breath, she's less sure of herself: "What'due south worse, looking jealous or crazy?" Beyoncé settles on crazy, so returns to anger. "You let this good honey become to waste." —O'Shaughnessy

22. "Weep Me a River," Justin Timberlake

Most breaking lyric: "You didn't know all the ways I loved you, no / So yous took a chance / 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 male child band era, and he was its charismatic face. (The cute one, if you will.) He even had the perfect girlfriend for that type of stardom: Britney Spears, with whom he pulled off this iconic denim fit. And then the couple broke up, JT divide from 'NSync, and "Cry Me a River" happened.

In his first solo megahit, Justin insinuates his love has cheated on him ("You don't have to say what you did / I already know, I found out from him") and writes her off for good. He's already cried well-nigh it, and now it'south her turn. Just no amount of her tears tin undo the damage; he'due south gone. Y'all didn't have to do much sleuthing to effigy out he was singing about Britney. That glory intrigue, Timbaland'due south sharp production, 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 stardom. He had split with not only Britney, but also his past, and he was ready for the globe. —Sayles

21. "With or Without You," U2

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

Naught changes if goose egg changes, as they say, and "With or Without You" exists in that hopelessly recursive "I detest that I love you" space. This song was U2'south start no. ane striking in the U.S., even though, Bono has said, "information technology's a very odd-sounding vocal … it kind of whispers its way into the world." But it's not the whispers that resonate most, notwithstanding, it's all those wails, similar the crescendo of Bono's aching, eminently singalong-able ahhh-ahhh-ahh-ahhhhhs, or the painful, everlasting notes from the Edge's "space guitar," engineered to hold a tone as if it were a grudge. "Psychotic restraint" is how Bono characterized the Edge's spare work on this runway, a description that could double as breakdown communication. —Katie Baker

xx. "Jolene," Dolly Parton

Virtually heartbreaking line: "And I tin can easily sympathise / How you could easily have my homo / But you don't know what he means to me, Jolene"

While other female country singers might've handled their man's newfound fascination with a cute redhead by, say, digging a key into the side of his pretty petty souped-up four-wheel drive, or—just spitballing here—threatening to send her to Fist City, Parton simply pleads for mercy. The desperate pitch of her entreatment, set against a frantic Dorian-mode guitar riff, sets the stakes far higher than those you might detect in by and large stern country songs about cheatin', lyin', and being untrue. Any armchair scholar of Parton'southward work tin tell you she cloaks feminist manifestos within marketable diddies nigh everyday experiences. I've ever taken the song'south urgency to imply something that every woman learns eventually: Relationships tin can be both romantically fulfilling, and, too often, an economic lifeboat to a improve life. In "Jolene," our narrator isn't just grasping onto her man, she'south grasping for survival. —Alyssa Bereznak

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

Most heartbreaking line: "Do yous plan to allow me become / For the other guy you loved earlier?"

This song was starting time released by Gladys Knight and the Pips in 1967. A year later on Marvin Gaye released a slower version of it on his album In the Groove. Perhaps the vocal resonated with Gaye because he married a 41-year-onetime woman when he was only 24, and their marriage was full of infidelities. "I was in love with the thought of love," Gaye once said. Or at least that's what I heard through the grapevine. —Heifetz

18. "Ex-Factor," Lauryn Loma

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

"Ex-Cistron" is more than than a breakup vocal, information technology's about recognizing a toxic relationship before yous 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 information technology. Hill's lyrics capture the worst of the worst of a relationship on the rocks: the pain, the complicity, and the unwillingness to give up on a love you think is nonetheless there, buried beneath the bullshit.

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

17. "Y'all're So Vain," Carly Simon

Almost heartbreaking line: "Well, you said that nosotros fabricated such a pretty pair / And that yous would never leave / But you gave away the things y'all loved / And one of them was me"

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

xvi. "Dancing on My Own," Robyn

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

Concluding twelvemonth, following a Robyn show at Madison Foursquare Garden, elated concertgoers continued the party on the A/C/E train subway platform, breaking into a giddy public operation of "Dancing on My Own." You wouldn't typically expect a breakup song to be the one that leads New Yorkers to such displays of collective joy, but nearly breakup songs aren't similar this one: a vocal yous tin strut to, a club anthem, a scene-stealer, a story of lonesomeness that nevertheless finds its solace in a crowd. Information technology's a song nearly moving on—I merely came to say bye—simply also about, just, moving. The vocalist might exist lone in the corner, and she might know it's stupid, but she'south out there dancing, at to the lowest degree. —Baker

15. "Thank U, Next," Ariana Grande

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

This song is a decision to be done with suffering over a 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 too to alive in the moment, to exist here now.

This to do the actual, day-in, twenty-four hours-out work of being happy. —Peters

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

Nigh heartbreaking line: "It's unnatural"

Both the joyous genesis and abject death knell for billions of '90s inferior-loftier-gymnasium-trip the light fantastic toe relationships that only lasted the length of the vocal itself, "Cease of the Road," which rose to power on 1992's Boomerang soundtrack, is one of the biggest hits in pop-music history. Like, "13 direct weeks atop the Hot 100" big. Like, "The 'One-time Town Road' of Its Solar day" big, a tearjerking shout-along anthem for lovelorn belters also devastated to even take their horses and leave the house. The final a capella chorus is a signature moment in American cultural history, at once exhilarating and devastating: "It'south unnatural / You belong to me / I belong to you." The give-and-take unnatural has never sounded then natural, and then miserable. —Harvilla

13. "Dreams," Fleetwood Mac

Most heartbreaking line: "Now here you go once more, you say you want your freedom / Well, who am I to keep you down?"

Even 40-plus years on, to hear Stevie Nicks softly moaning, "What y'all 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 class, has been known to belt out a sweetly caustic breakdown anthem or two himself.) As the second (and best!) rails on 1977'southward zillions-selling Rumours, "Dreams" is both radically overexposed and still somehow criminally underrated, fixed to its iconic place, time, and circumstances just also shockingly timeless. (Zoë Kravitz rhapsodizes it in the pilot of Hulu's new High Allegiance remake series to bear witness her stone-nerd bona fides.) Pair it with "Silver Springs" for maximum issue. —Harvilla

12. "How Can You Mend a Broken Heart," Al Dark-green

About heartbreaking line: "Let me live again"

In that location's heartbreak, and so there'south Al Green heartbreak. (Not to slight the original Bee Gees version—Light-green is all I know when I'one thousand going through it.) He'southward exasperated from the offset, wondering whether he'll ever recover from the dear that went away. The agony is enough to contemplate nature itself in the chorus: "How can you mend a broken heart? / How can yous finish the rain from falling down? / How can you stop the sun from shining? / What makes the globe go round?" Light-green is begging for answers, for "somebody, please" to come ready him. He pleads, "Permit me alive again." Life as he knew information technology is over without this person, and as long every bit the vocal is on, information technology feels over for usa, besides. —O'Shaughnessy

eleven. "Torn," Natalie Imbruglia

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

There's a bad breakdown, there's rock bottom, and then there's being "common cold and shamed, lying naked on the flooring." Natalie Imbruglia'due south 1997 one-hit wonder (and sneaky cover) doesn't mince words in describing exactly how shitty it feels to put your faith in the incorrect man. (Or any man, depending on how hard you lot vibe with this vocal.) "Torn" has taken a turn for the over-covered and over-memed these days, but you're lying if you say y'all don't still hit that chorus every time. —Halliwell

x. "I Volition Survive," Gloria Gaynor

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

This 1978 disco colossus is so atypical, then monolithic, and then wedding-dancefloor-ingrained that it hardly scans as a breakup song at all: As ecstatic and empowering fuck-you anthems go, it is the glamorous grandmother to Lizzo's "Truth Hurts" and Ariana Grande's "Thank U, Next" and Beyoncé'south "Irreplaceable" and roughly 50,000 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 bluntly iconic line "I'm saving all my lovin' for someone who's lovin' me," which of course is everybody. She knows you're afraid; she knows yous're petrified. Merely she likewise knows you lot won't stay that way for long. —Harvilla

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

About heartbreaking line: "Wonder this time where she'due south gone / Wonder if she'southward gone to stay"

To make 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 considering EA Dante has rippling muscles and a massive scythe, his only protections against the legions of the nighttime, who've stolen his honey Beatrice. I never played it, but a friend who did described his frustration with the game: It's equally if its determination got further away the more time he devoted to it. A Super Basin commercial showed Dante sprinting toward Hell's gaping rima oris determined but, you know, definitely doomed. As he descends you lot hear the low croak of Bill Withers'due south vocalization, pining after a lost lover: "Ain't no sunshine when she's gone, but darkness everyday." My last breakup didn't involve a giant flaming devil monster, simply it did feel similar a similarly hopeless uphill boxing. —Peters

eight. "Someone Similar Yous," Adele

Almost heartbreaking line: "Sometimes it lasts in dearest, but sometimes it hurts instead"

The queen of heartbreak has never been better than on sophomore album 21, and 21 doesn't become much better than "Someone Similar You lot." Adele's ode to the ane who got abroad is perchance the about universally adored tearjerker of the past decade; starting with that simple pianoforte line and ending in that burdensome hook: "Sometimes it lasts in love, just sometimes it hurts instead." And of class, that voice! Watching the simple black and white music video at present, it'southward striking how baby-faced Adele was at 21, despite her commitment of a song that displays and then much emotional maturity. She wishes the best for her ex ("Former friend, why are you then shy?"), just damn, she's all the same hurting. Aren't we all! —Halliwell

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

Most heartbreaking lyrics: "Someone picked you from the bunch, one glance was all it took / At present it's much too belatedly for me to take a second await"

Possibly the most outwardly joyous song in this unabridged ranking, "I Desire Yous Dorsum" spins a tale that anyone who'southward ever taken someone for granted will understand. An 11-yr-former Michael Jackson is at his near precocious here, singing nigh the daughter whom he didn't fully appreciate until someone else stole her heart. At present he only wants some other adventure to prove that he knows how to care for her right. Michael, of course, didn't write the vocal—it was penned by Berry Gordy and Co.—but he sells it in a way that someone two or three times his historic period never could. A leopard can't change its spots, but if information technology sounds this good trying to convince you it can, why not give it one more chance? —Sayles

vi. "Since U Been Gone," Kelly Clarkson

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

There is a moment in every breakup where, afterward a few weeks of self-pity, you shed your sweatpant cocoon, step outside, and, with the instantaneity of a safety band snap, of a sudden know deep within your heart that your ex was an insufferable blowhard. Kelly Clarkson'southward mosh-adjacent power pop ballad embodies the newfound cocky-assurance that comes with that realization. It likewise happens to exist enshrined in a popular culture moment that I will forever acquaintance with being a melodramatic xvi-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 than poetic Yeah Yeah Yeahs hitting, "Maps," and and then—after being passed up by both Pink and Hilary Duff—was sung by the very first winner of the so-fledgling reality TV testify American Idol. The AIM-friendly "U" in the championship is but the icing on the cake. —Bereznak

v. "Ms. Jackson," Outkast

Nigh heartbreaking lyric: "Forever never seems that long until you're grown / And notice that the day-by-24-hour interval ruler tin't exist too wrong"

Sometimes breaking upwardly with your meaning other's family unit is only every bit hard equally breaking upwardly with them. Big Boi and André 3000 understood that on "Ms. Jackson," a song dedicated to Kolleen Maria Wright, the mother of Erykah Badu, with whom André had a child. Three Stacks's poetry is especially poignant—his intentions were good, but things took a turn for the worse. It's a harsh reality: Nigh relationships are built-in with an expiration appointment, no thing how bright the flame burned at the offset. As far as apology songs become, it's pretty nuanced and sincere. And Wright seems to accept bought it: Erykah said in 2016 that her mother even has a "MSJACKSON" license plate. —Sayles

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

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

Dolly Parton wrote one of the most dynamic love songs ever with "I Will E'er Love You." Whitney Houston, who sang a cover for the movie The Bodyguard, made a worldwide hit with her astounding range. Both versions are wonderful for different reasons, though Parton's honeyed, wobbly original is best for heartbreak. For one, it'south authentic: She wrote the song for her former manager and professional partner, Porter Wagoner, later on she decided to leave him. Parton is sympathetic, yet adamant to go. Equally she sings in the span, it's bittersweet. They are both better off this style, she argues, but wishes him nothing but "joy and happiness." 1 of the hardest relationship lessons is that two people can love each other and it still not be right for either—thanks to Dolly and Whitney, it was one learned early on. —O'Shaughnessy

3. "I Can't Brand Y'all Love Me," Bonnie Raitt

Virtually heartbreaking line: "I'll shut my eyes / Then I won't come across / The beloved you don't feel when y'all're belongings me"

You might be a girlfriend, a husband, a partner, or fifty-fifty a friend with benefits. Whatever role yous play in service of beloved, it comes with a label that sets expectations. There is clarity and comfort in knowing where you stand with someone. But despite all of our semantics and promises, the terrifying reality of our love lives is that love itself tin exist a ruthlessly nonbinding agreement, an at-will arrangement. Even more than frightening is that it's oftentimes our hearts—not the states—calling the shots.

What sets "I Can't Make You Beloved Me" apart from well-nigh breakup songs is that information technology takes place at the about painful point of a breakup: acceptance. Information technology's not a mail service-breakdown canticle of empowerment or a desperate plea to stay together. It's the full force of the disorienting i-two punch of loss and loneliness. It'southward the world-shattering moment when y'all give upward the fight.

Bonnie Raitt's arresting operation of this song (written by Mike Reid and Allen Shamblin) carries the weight of a lifetime in and out of love. She sets downward her slide guitar, sits Bruce Hornsby down at the piano, and sings the accented fuck out of this song with confidence and grace. The song used on the Luck of the Draw album recording was Bonnie'southward beginning take. "I Can't Make You Love Me" has been covered by endless artists, included on several Greatest Songs Of All Time lists, and inducted into the Grammy Hall of Fame.

The songs that touch us most deeply are the ones that unite united states of america through the nigh homo of shared experiences. Eventually, nosotros all larn that you can't make someone's heart experience "something it won't." But should you ane mean solar day find yourself at rock bottom, suddenly alone in darkness—whether information technology'south your first time or your 14th—y'all tin feel a niggling fleck less alone knowing that Bonnie's been at that place, too. —James

2. "You Oughta Know," Alanis Morissette

Well-nigh heartbreaking line: "Does she know how you lot told me you'd concur me until you died, till yous died / Just yous're however live"

Alanis Morrisette was 19 years old when she recorded that ballad of bitterness "Yous Oughta Know" in one take at 11 p.m. "All those vocals are just her at the terminate of the night," said her cowriter Glen Ballard in an oral history of the album Jagged Little Pill, "singing something she just wrote." The consequence 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 perhaps inspired by Uncle Joey remains both iconic and deeply weird, but also makes sick sense: You oasis't truly been jilted until you've been jilted by someone who's not even that absurd, you know?) "You Oughta Know" totally scandalized my mom every time it came on the radio in the '90s, and what'due south more than, it features both Flea on bass and Dave Navarro on the guitar. What more could you want—other than sweet, sweet vengeance? —Baker

1. "Royal Rain," Prince

Most heartbreaking line: "I never meant to crusade you any sorrow / I never meant to cause yous any pain"

Purple rain, according to an unsourced quote that's widely attributed to Prince Rogers Nelson, is the result of blood mixing with the heaven, which is a sort of apocalyptic drama that only Prince could conjure. But you don't even demand to empathise what purple rain is to experience "Purple Pelting," a power ballad to end all power ballads.

Some breakup songs are hateful, some are mournful, others are empowering. Only "Purple Rain" has the power to feel like everything all at once, a nearly-religious experience of a song that has the ability to heal similar no other. In times of trouble, put "Majestic Pelting" 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