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

We here 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. Below, you’ll find our ranking of the 50 greatest breakup songs of all time, as voted on by our staff. The list spans several decades and many different moods, but all are rooted in some type of pain. There was only one rule for the final ranking: just one song per artist was included to avoid Dolly Parton or even Drake from dominating.

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

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

Most heartbreaking line: “You would hide away and find your peace of mind / With some indie record that’s so much cooler than mine”

One of the most savage breakup songs in history, “We Are Never Ever Getting Back Together” encapsulates the severe “fuck that guy!” energy that follows a long-overdue parting of ways. We’ve all had that post-fight rant with our friends: “Ugh … so he calls me up and he’s like, ‘I still love you,’ and I’m like … ‘I just … I mean this is exhausting, you know, like, we 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,” Blink-182

Most heartbreaking line: “I need somebody and always / This sick strange 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 second verse. It’s part of the grand pop punk tradition of showing you mean business by going up an octave, of which “I Miss You” (along with the Starting Line’s “The Best of Me”) is the exemplar.

Don’t just take my word 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 song.” —Michael Baumann

48. “It’s Too Late,” Carole King

Most heartbreaking line: “But we just can’t stay together, don’t you feel it, too? / Still I’m glad for what we had and how I once loved you”

“It’s Too Late” is a crushing ode to the most common kind of breakup. The natural process of two people growing apart is as heartbreaking as it is commonplace, and King sings in a tone perfectly situated between her sorrow and the shrugging admission that “we really did try to make it.” Her conversational delivery early 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 us is changing, or maybe we just stopped trying,” she sings, plainly laying out the central, blameless reasons for why most people end up 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-Break My Heart,” Toni Braxton

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

This is a perfect example of the kind of breakup song you hear on the radio (or, in the late ’90s, possibly the club—the Frankie Knuckles house remix still goes) and, on a normal day, just hear another pop song, but when you’re experiencing heartache, what originally sounded like songwriting clichés become the truest words you’ve ever heard. “I have cried a lot of nights,” you think, getting out of bed for the first time in days to grab a roll of toilet paper since you ran out of Kleenex. “Life is cruel without you here beside me,” you murmur, staring into the bleak chasm of loneliness you now know as life. “I would literally do anything on God’s green earth to hear you say you love me again,” you realize with the greatest clarity you’ve ever experienced. Anyway, where are my altos at? This is our karaoke song. —Kjerstin Johnson

46. “Mr. Brightside,” the Killers

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

Maybe it’s not exactly right to call “Mr. Brightside” a breakup song; maybe it’s more accurate to 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. But that’s all really clunky, so let’s accept being slightly incorrect for the sake of cleanliness. Either way, “Mr. Brightside” is an iconic mid-aughts song that’s perfect for yell-karaoking and that pulls off the difficult trick of just repeating one verse over and over. Also, Eric Roberts in the video. —Andrew Gruttadaro

45. “She’s Gone,” Hall & Oates

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

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 hit from their second album, 1973’s oddly/heartbreakingly named Abandoned Luncheonette. “She’s Gone” is luscious and silky and deceptively light, all Motown grandeur by way of blue-eyed Philly soul, but that lightness only underscores the exquisite heaviness of murmured verse lines like “Get up in the morning, look in the mirror / Worn as the toothbrush hanging in the stand.” (Or probably it’s “One less toothbrush,” which of course is even heavier.) The chorus, by contrast, is gigantic and majestic and crushing, punctuated by cloudbursting lamentations of “She’s gone! / Oh why? / Oh why?” The boys only got bigger from here, but they certainly never got sadder. —Rob Harvilla

44. “Tyrone,” Erykah Badu

Most heartbreaking line: “I just want it to be, you and me, like it used to be, baby / But ya don’t know how to act”

The second-best moment on this viciously sultry slow jam, the crown jewel of Erykah Badu’s 1997 album Live, is the stupendous opening line: “I’m gettin’ tired of your shit / You don’t ever buy me nothin’.” The first-best moment is all the women in the crowd immediately shrieking with delight and, one fears, recognition. “Tyrone” is named for one of an unnamed deadbeat lover’s numerous deadbeat friends: “Every time we go somewhere,” Badu purrs with lethal authority, “I gotta reach down in my purse / To pay your way and your homeboy’s way and sometimes your cousin’s way.” It is the gender-flipped riposte to Friday’s “Bye, Felicia,” and in fact turned up as a joke in 2000’s Next Friday; it “followed me thru my career like an obsessed X boyfriend,” as Badu put it on Instagram in 2017, while shouting out her backup singers, whose sardonic and sublime “Call him!” chant is the third-best moment. —Harvilla

43. “Love Is a Battlefield,” 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 not so much a breakup as a near-breakup in progress, an acknowledgement that true love means almost breaking up pretty much all the time: “Believe me / Believe me / I can’t tell you why / But I’m 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 smash of eternal profundity, and a striking declaration that sometimes the only thing worse than splitting up is not splitting up: “Do I stand in your way / Or am I the best thing you’ve had?” she wails with genuine desperation, and the answer, of course, is both. —Harvilla

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

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

We’re not even talking about the whole song—we’re talking about 20 or so seconds of Bink production after Kanye’s second verse, but before Rick Ross’s only verse, arguably one of the best in his career. In it, he describes West’s near-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 like on this bridge. A climb up the Lord’s ladder, a departure from Earth, a one-way trip to anywhere but here. —Micah Peters

41. “Suspicious Minds,” Elvis Presley

Most heartbreaking line: “We can’t go on together / With suspicious minds / And we can’t build our dreams / On suspicious minds”

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

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

Most heartbreaking lines: “Although she may be cute, she’s just 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 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’s dating someone new, but he’s not thinking of her. (Side note: I don’t know who I’m sadder for here, Smokey or the rebound he’s walking around town with.) He may have wiped away the tears, but they’ve left their mark. And the makeup only makes the tear tracks that much more apparent. —Justin Sayles

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

Most heartbreaking line: “So this is inevitable withdrawal / Even if I stop wanting you / 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 just be my own best friend,” she warns. “Not fuck myself in the head with stupid men.” These lines that pried the song open were one of Winehouse’s hallmarks as a writer—“Tears” begins in the dumps, in the aftermath. But 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 being such a dumb, whiny baby. —Peters

38. “Needed Me,” Rihanna

Most heartbreaking lines: “Fuck your white horse and a carriage / Bet you never could imagine / Never told you you could have it / You needed me”

This song is so petty and I love it. Rihanna basically made a hit off the “Sike, you thought!” meme and DJ Mustard added an unforgettable beat behind it. This is one of those bangers that you and your girls blast post-breakup, pre-going-out. Then, after you all sing in unison: “Don’t get it twisted / You was just another nigga on the hit list / Tryna fix your inner issues with a bad bitch,” you all burst into laughter thinking about the man who is now barely a memory. Rihanna’s confidence and savageness is really on an untouchable level. (Remember, this song is on the same album where she sings “sex with me is so amazing” over and over.) Long may she reign. —Jordan Ligons

37. “So Sick,” Ne-Yo

Most heartbreaking line: “Gotta change my answering machine, now that I’m alone / ’Cause right now it says that we can’t come to the phone”

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

36. “We Belong Together,” Mariah Carey

Most heartbreaking line: “When you left I lost a part of me / It’s still so hard to believe / Come back baby, please / ‘Cause we belong together”

*Sighs.* This is easily the most 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. But now if it comes on the radio and you’re either happily single or in a solid relationship, your eyes will glaze over, guaranteed. When the first two seconds of the infamous beat come through my speakers, I’m already changing the station. It’s just so annoying, and so Mariah.

You may think 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 sun comes up, but let me tell you, you will and you’ll be fine. Breakups suck, but please don’t torture your broken heart (or your ears) by listening to this song on repeat. —Ligons

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

Most heartbreaking line: “Say for me that I’m all right, 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’s masterful Blood on the Tracks has always been debated. Critics have long assumed that the album is about 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 it’s 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, it doesn’t matter. Blood strikes such a chord because the heartache it mines feels at once deeply personal and universal.

That’s most palpable on “If You See Her, Say Hello,” which brings us into a fractured relationship in a way that’s both effortlessly relatable (“We had a falling out, like lovers often will”) and hyper-specific (“And to think of how she left that night, it still brings me a chill”). It’s not Dylan’s flashiest or heaviest or best song, but it is my favorite, a gentle, intimate portrait of lost love and lasting anguish. Like so much of his best work, it’s propelled by its poetry, the raw insights about how it feels to be alive. The song cycles through the same phases that so many of us do while processing heartbreak: denial, despair, anger, desire. It floats on a current of remorse (“Sundown, yellow 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, cautiously, back toward hope (“If she’s passing back this way, I’m not that hard to find / Tell her she can look me up, if she’s got the time”). After enough listens, and enough heartache of your own, you realize that “If You See Her, Say Hello” isn’t really a breakup song. It’s a love letter. —Mallory Rubin

34. “Don’t Look Back in Anger,” Oasis

Most heartbreaking line: “Stand up beside the fireplace / Take that look from off your face / ’Cause you ain’t ever gonna burn my heart out”

The closest I’ve ever come to living in an episode of Glee was when my high school French class spontaneously broke out singing “Don’t Look Back in Anger.” I don’t remember why, but it cemented this song (at least for me) as a ballad of communal weltschmerz, rather than personal sadness or regret, like a fin-de-siècle “You’ll Never Walk Alone.” (For instance: “Don’t Look Back in Anger” became a kind of unofficial anthem after the Manchester bombing in 2017.) Oasis knows a thing or two about writing for the communal sing-along, the importance of the languid, memorable melody 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 Breath You Take,” the Police

Most heartbreaking line: “Since you’ve gone I’ve been lost without a trace / I dream at night, I can only see your face”

This spectacularly maudlin New Wave ballad, which anchored the Police’s 1983 goliath Synchronicity and reigned as one 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 love in terms of surveillance as it describes total state surveillance in terms of spurned love: “Every move you make / Every vow you break / Every smile you fake / Every claim you stake.” And so on. “I’ll be watching you,” Sting concludes a couple dozen times throughout, but it’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 Bond author’s luxe Jamaican estate, which might not be creepy, but it’s certainly weird. —Harvilla

32. “Don’t Speak,” No Doubt

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

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

No Doubt’s first hit 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: “Do you not think so far ahead? / ‘Cause I been thinkin’ bout forever”

Sometimes you have to lie to yourself to get through heartache. They weren’t good enough for me. I can do better. I didn’t love them, I just thought they were cute. Frank Ocean’s “Thinkin Bout You” exposes that kind of posturing for what it is: a facade. No, I wasn’t crying about you, and by the way, I also own waterfront property in Idaho. Frank’s clearly still hung up on the past even if his old flame isn’t. And the only way to work through the pain is to drop the lying and come clean with himself. It’s tender, it’s sweet, but most of all, it’s honest. —Sayles

30. “I’m Goin’ Down,” Mary J. Blige

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

No matter your current relationship status, you will for sure sing your heart out when this song comes on. I do not care, I am Mary J. when the chorus hits. By the end of the song—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’s up-[dramatic pause]-side down!” I can’t be the only one, right?

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

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

Most heartbreaking lines: “I could put my arms around every boy I see / But 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. But the breakup sticks with you. You run into your ex’s best 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 can’t think of a song that better captures that duality than “Nothing Compares 2 U,” the 1990 O’Connor hit originally penned by Prince in 1985. You can do whatever you want: You can party all night, you can eat at a fancy restaurant, you can put your arms around all the boys and girls you’d like, but it doesn’t matter. It’s not them, and nothing will be. Your best hope is just giving in and living for yourself. —Sayles

28. “Marvin’s Room,” Drake

Most heartbreaking line: “The woman that I would try / Is happy with a good guy”

Drake is at his best when he’s destructive because he masks the gaslighting with a softer sadness. “The woman that I would try / Is happy with a good guy,” he sings. Is he happy for her? The lines suggest that there’s at least a chance. Drake pauses, then goes full Drizzy Deleterious: “But I’ve been drinkin’ so much / That I’ma call her anyway.” He proceeds to tell her that the man she’s with isn’t good enough to replace what they had. It’s 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 it is about her. Drake spirals, telling her he’s “had sex four times this week / I can explain,” that he’s sponsoring women, that he can’t stop partying and asking for naked pictures. Exactly what your ex-girlfriend wants to hear, I’m sure. At least there’s a voicemail interlude. —Haley O’Shaughnessy

27. “Just a Friend,” Biz Markie

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

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

Biz. My guy. Sit down. Let’s talk. First off, she was not your girl. You met her one time. Second, you did not catch her tongue-kissing a dude. You stalked her. Third, 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 about his predicament. You know, a friend. —Danny Heifetz

26. “Burn,” Usher

Most heartbreaking line: “But you know, gotta let it go / ’Cause the party ain’t jumpin’ like it used to / Even though this might bruise you / Let it burn”

I couldn’t imagine someone breaking up with me with the lyrics to this song. Usher is all over the place. He says he loves me, but our relationship has to come to an end; he says he’s hurting and he’s not happy, but he’s breaking down and crying. Deep down he knows it’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. It preaches the ideology of forcing yourself to let go even when you don’t know what you’re going to do without your boo. After a heartbreak, everyone has found themselves teetering on the line between regret and freedom. Usher’s “Burn” allows you to tap into that while simultaneously yelling out, “It’s been fifty-eleven days, umpteen hours, and Imma be burnin’ till you return!” —Ligons

25. “Piece of My Heart,” Big Brother & the Holding Company

Most heartbreaking line: “But each time I tell myself that I, well I can’t stand the pain / But when you hold me in your arms, I’ll sing it once again”

If you’re ever at your wits’ end, tragically obsessed with someone who treats you like shit, you can find some catharsis in the controlled chaos of Janis Joplin’s vocal performance on “Piece of My Heart.” Go ahead and scream along. You won’t sound as good as Janis, but you’ll certainly feel a hell of a lot better 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’s Aretha’s older sister). Or if you need some more twang accompanying your despair, you can try the Faith Hill version. I also won’t judge you if the only person who can ease your pain is Shaggy (or Beverley Knight, Melissa Etheridge, Steven Tyler, Kelly Clarkson, or one of countless other artists).

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

24. “Skinny Love,” Bon Iver

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

A good rule for breakup songs is that there has to be a part that you can yell along to, unencumbered by silly things like constraint and self-awareness. The chorus of Bon Iver’s “Skinny Love” has a great one, especially for anyone who’s just 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 up his car, and drove into the Wisconsin wilderness, emerging only after recording an album of weepy breakup 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 Love”—are profoundly reflective, intelligent, moving documents about the breakdown of a relationship. —Gruttadaro

23. “Hold Up,” Beyoncé

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

It’s hard to express real hurt over an uptempo beat and make the heartbreak convincing. Yet Beyoncé is believable in “Hold Up,” a painful accounting of the emotions that come after discovering that your partner has cheated. Lemonade was inspired by true events—i.e., it’s Beyoncé coming to terms with Jay-Z being unfaithful. Infidelity brings on a very specific type of devastation: You’re mad; you’re miserable; you’re humiliated. You switch from one emotion to another in a matter of minutes. She opens the song with confidence: No other woman can give what she can. “Hold up, they don’t love you like I love you.” In a breath, she’s less sure of herself: “What’s worse, looking jealous or crazy?” Beyoncé settles on crazy, then returns to anger. “You let this good love go to waste.” —O’Shaughnessy

22. “Cry Me a River,” Justin Timberlake

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

Entering 2002, Justin Timberlake wasn’t regarded as much more than a teeny bopper. His group ’NSync was one of the defining groups of the boy 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. Then the couple broke up, JT split 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 about it, and now it’s her turn. But no amount of her tears can undo the damage; he’s gone. You didn’t have to do much sleuthing to figure out he was singing about Britney. That celebrity intrigue, Timbaland’s 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 another level of stardom. He had split with not only Britney, but also his past, and he was ready for the world. —Sayles

21. “With or Without You,” U2

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

Nothing changes if nothing changes, as they say, and “With or Without You” exists in that hopelessly recursive “I hate that I love you” space. This song was U2’s first no. 1 hit in the U.S., even though, Bono has said, “it’s a very odd-sounding song … it kind of whispers its way into the world.” But it’s not the whispers that resonate most, however, it’s all those wails, like the crescendo of Bono’s aching, eminently singalong-able ahhh-ahhh-ahh-ahhhhhs, or the painful, everlasting notes from the Edge’s “infinite 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 track, a description that could double as breakup advice. —Katie Baker

20. “Jolene,” Dolly Parton

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

While other female country singers might’ve handled their man’s newfound fascination with a beautiful redhead by, say, digging a key into the side of his pretty little 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 appeal, set against a frantic Dorian-mode guitar riff, sets the stakes far higher than those you might find in generally stern country songs about cheatin’, lyin’, and being untrue. Any armchair scholar of Parton’s work can tell you 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 It Through the Grapevine,” Marvin Gaye

Most heartbreaking line: “Do you 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 it on his album In the Groove. Perhaps the song resonated with Gaye because he married a 41-year-old woman when he was only 24, and their marriage was full 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

18. “Ex-Factor,” Lauryn Hill

Most heartbreaking line: “Where were you when I needed you?”

“Ex-Factor” is more than a breakup song, it’s about recognizing a toxic relationship before you have the words to call it a toxic relationship. Each line, so honest it hurts, is about the fruitless search for reason in a scenario devoid of it. Hill’s lyrics capture the worst of the worst of a relationship on the rocks: the pain, the complicity, and the unwillingness to give up on a love you think is still there, buried beneath the bullshit.

When it hit airwaves again in 2018 on Drake’s pandering yet irresistible “Nice for What,” it was almost like recognizing and reclaiming a past self—one who might have cried along to the original. Now, as wiser, more 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. Still, no one 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, you said that we made such a pretty pair / And that you would never leave / But you gave away the things you 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 world wondering whom it was about and what they could’ve possibly done to anger her. More than 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 three separate men, Beatty “thinks the whole thing is about him.”) We may never know what company he kept (cough: Mick Jagger?), but the lasting power of Simon’s clear-eyed takedown stands as a referendum on the unchecked male ego, whether its contained in the body of a dashing actor or a moody fuckboy. —Bereznak

16. “Dancing on My Own,” Robyn

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

Last year, following a Robyn show at Madison Square Garden, elated concertgoers continued the party on the A/C/E train subway platform, breaking into a giddy public performance 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 most breakup songs aren’t like this one: a song you can strut to, a club anthem, a scene-stealer, a story of lonesomeness that still finds its solace in a crowd. It’s a song about moving on—I just came to say goodbye—but also about, just, moving. The singer might be alone in the corner, and she might know it’s stupid, but she’s out there dancing, at least. —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 not only rehearse past losses but to envision future victories, and also to live in the moment, to be here now.

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

14. “End of the Road,” Boyz II Men

Most heartbreaking line: “It’s unnatural”

Both the joyous genesis and abject death knell for billions of ’90s junior-high-gymnasium-dance relationships that only lasted the length of the song itself, “End of the Road,” which rose to power on 1992’s Boomerang soundtrack, is one of the biggest hits in pop-music history. Like, “13 straight weeks atop the Hot 100” big. Like, “The ‘Old Town Road’ of Its Day” big, a tearjerking shout-along anthem for lovelorn belters too devastated to even take their horses and leave the house. The final a capella chorus is a signature moment in American cultural history, at once exhilarating and devastating: “It’s unnatural / You belong to me / I belong to you.” The word unnatural has never sounded so natural, and so miserable. —Harvilla

13. “Dreams,” Fleetwood Mac

Most heartbreaking line: “Now here you go again, 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 you had … and what you lost / And what you had … and what you lost” to the guy playing guitar is to live forever, and to imagine that guitar player dropping dead from remorse on the spot. (Lindsey Buckingham, of course, has been known to belt out a sweetly caustic breakup anthem or two himself.) As the second (and best!) track on 1977’s zillions-selling Rumours, “Dreams” is both radically overexposed and still somehow criminally underrated, fixed to its iconic place, time, and circumstances but also shockingly timeless. (Zoë Kravitz rhapsodizes it in the pilot of Hulu’s new High Fidelity remake series to prove her rock-nerd bona fides.) Pair it with “Silver Springs” for maximum effect. —Harvilla

12. “How Can You Mend a Broken Heart,” Al Green

Most heartbreaking line: “Let me live again”

There’s heartbreak, and then there’s Al Green heartbreak. (Not to slight the original Bee Gees version—Green is all I know when I’m going through it.) He’s exasperated from the beginning, wondering whether he’ll ever recover from the love that went away. The agony is enough to contemplate nature itself in the chorus: “How can you mend a broken heart? / How can you stop the rain from falling down? / How can you stop the sun from shining? / What makes the world go round?” Green 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, too. —O’Shaughnessy

11. “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”

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

10. “I Will Survive,” Gloria Gaynor

Most heartbreaking line: “And so you 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, so monolithic, so 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’s “Irreplaceable” and roughly 50,000 other self-affirming pop hits. What truly elevates New 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 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 you’re petrified. But she also knows you won’t stay that way for long. —Harvilla

9. “Ain’t No Sunshine,” Bill Withers

Most heartbreaking line: “Wonder this time where she’s gone / Wonder if she’s gone to stay”

To make a song from 1971 about 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 against the legions of the night, who’ve stolen his beloved Beatrice. I never played it, but a friend who did described his frustration with the game: It’s as if its conclusion got further away the more time he devoted to it. A Super Bowl commercial showed Dante sprinting toward Hell’s gaping mouth determined but, you know, definitely doomed. As he descends you hear the low croak of Bill Withers’s voice, pining after a lost lover: “Ain’t no sunshine when she’s gone, only darkness everyday.” My last breakup didn’t involve a giant flaming devil monster, but it did feel like a similarly hopeless uphill battle. —Peters

8. “Someone Like You,” Adele

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

The queen of heartbreak has never been better than on sophomore album 21, and 21 doesn’t get much better than “Someone Like You.” Adele’s ode to the one who got away is perhaps the most universally adored tearjerker of the past decade; starting with that simple piano line and ending in that crushing hook: “Sometimes it lasts in love, but sometimes it hurts instead.” And of course, that voice! Watching the simple black and white music video now, it’s striking how baby-faced Adele was at 21, despite her delivery of a song that displays so much emotional maturity. She wishes the best for her ex (“Old friend, why are you so shy?”), but damn, she’s still hurting. Aren’t we all! —Halliwell

7. “I Want You Back,” The Jackson 5

Most heartbreaking lyrics: “Someone picked you from the bunch, one glance was all it took / Now it’s much too late for me to take a second look”

Perhaps the most outwardly joyous song in this entire ranking, “I Want You Back” spins a tale that anyone who’s ever taken someone for granted will understand. An 11-year-old 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 just wants another chance to prove that he knows how to treat her right. Michael, of course, didn’t write the song—it was penned by Berry Gordy and Co.—but he sells it in a way that someone two or three times his age never could. A leopard can’t change its spots, but if it sounds this good trying to convince you it can, why not give it one more chance? —Sayles

6. “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 you) / I guess you never felt that way”

There is a moment in every breakup where, after a few weeks of self-pity, you shed your sweatpant cocoon, step outside, and, with the instantaneity of a rubber band snap, suddenly know deep within your heart that your ex was an insufferable blowhard. Kelly Clarkson’s mosh-adjacent power pop ballad embodies the newfound self-assurance that comes with that realization. It also happens to be enshrined in a pop culture moment that I will forever associate with being a melodramatic 16-year-old millennial: “Since U Been Gone” was written by pop lords Max Martin and Dr. Luke, who ripped its entire musical structure from the far more poetic Yeah Yeah Yeahs hit, “Maps,” and then—after being passed up by both Pink and Hilary Duff—was sung by the very first winner of the then-fledgling reality TV show American Idol. The AIM-friendly “U” in the title is just the icing on the cake. —Bereznak

5. “Ms. Jackson,” Outkast

Most heartbreaking lyric: “Forever never seems that long until you’re grown / And notice that the day-by-day ruler can’t be too wrong”

Sometimes breaking up with your significant other’s family is just as hard as breaking up with them. Big Boi and André 3000 understood that on “Ms. Jackson,” a song dedicated to Kolleen Maria Wright, the mother of Erykah Badu, with whom André had a child. Three Stacks’s verse is especially poignant—his intentions were good, but things took a turn for the worse. It’s a harsh reality: Most relationships are born with an expiration date, no matter how bright the flame burned at the beginning. As far as apology 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

4. “I Will Always Love You,” Whitney Houston

Most heartbreaking line: “Please don’t cry / We both know I’m not what you, you need”

Dolly Parton wrote one of the most dynamic love songs ever with “I Will Always 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’s authentic: She wrote the song for her former manager and professional partner, Porter Wagoner, after she decided to leave him. Parton is sympathetic, yet determined to go. As she sings in the bridge, it’s bittersweet. They are both better off this way, she argues, but wishes him nothing but “joy and happiness.” One 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 Make You Love Me,” Bonnie Raitt

Most heartbreaking line: “I’ll close my eyes / Then I won’t see / 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 role you play in service of love, 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 can be a ruthlessly nonbinding agreement, an at-will arrangement. Even more frightening is that it’s often our hearts—not us—calling the shots.

What sets “I Can’t Make You Love Me” apart from most breakup songs is that it takes place at the most painful point of a breakup: acceptance. It’s not a post-breakup anthem of empowerment or a desperate plea to stay together. It’s the full force of the disorienting one-two punch of loss and loneliness. It’s the world-shattering moment when you give up the fight.

Bonnie Raitt’s arresting performance of this song (written by Mike Reid and Allen Shamblin) carries the weight of a lifetime in and out of love. She sets down her slide guitar, sits Bruce Hornsby down at the piano, and sings the absolute fuck out of this song with confidence and grace. The vocal used on the Luck of the Draw album recording was Bonnie’s first take. “I Can’t Make You 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 most deeply are the ones that unite us through the most human of shared experiences. Eventually, we all learn that you can’t make someone’s heart feel “something it won’t.” But should you one day find yourself at rock bottom, suddenly alone in darkness—whether it’s your first time or your 14th—you can feel a little bit less alone knowing that Bonnie’s been there, too. —James

2. “You Oughta Know,” Alanis Morissette

Most heartbreaking line: “Does she know how you told me you’d hold me until you died, till you died / But you’re still alive”

Alanis Morrisette was 19 years old when she recorded that ballad of bitterness “You Oughta Know” in one take at 11 p.m. “All those vocals are just her at the end of the night,” 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 it was possibly inspired by Uncle Joey remains both iconic and deeply weird, but also makes sick sense: You haven’t truly been jilted until you’ve been jilted by someone who’s not even that cool, you know?) “You Oughta Know” totally scandalized my mom every time it came on the radio in the ’90s, and what’s more, it features both Flea on bass and Dave Navarro on the guitar. What more could you want—other than sweet, sweet vengeance? —Baker

1. “Purple Rain,” Prince

Most heartbreaking line: “I never meant to cause you any sorrow / I never meant to cause you 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 sky, which is a sort of apocalyptic drama that only Prince could conjure. But you don’t even need to understand what purple rain is to feel “Purple Rain,” a power ballad to end all power ballads.

Some breakup songs are hateful, some are mournful, others are empowering. Only “Purple Rain” has the ability to feel like everything all at 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