The Saddest Breakup Songs Of All Time

Illustrated by Sydney Hass.
The Ronettes had it all wrong. The best part of breaking up is not the making up. That rarely happens, and when it does, it often leads to more breaking up.
No, the real pleasure in having your soul shredded by another human being comes in the days, weeks, months, or maybe even years of wallowing that follow. It’s a chance to wear pajama bottoms past noon and indulge in some serious self-reflection — the type that makes you a stronger, better person. This journey into the self can be scary, but luckily, generations of musicians have written songs to soundtrack the plunge.
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What follows are the saddest (and therefore finest) breakup songs of all time. On this list you’ll find no TSwizz “We’re Never Ever Getting Back Together" (too empowering) or Alanis Morissette “You Oughta Know” (too angry). These songs are plain and simple, rip-your-heart-out sad. Play ‘em just loud enough to drown out the sobbing.
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Mark Ronson feat. Miley Cyrus "Nothing Breaks Like a Heart"

Sure, you love Miley's party songs but she can really break your heart as well. This pair-up with producer Mark Ronson yields a world-weary track about the pains of a broken heart and the trials of getting through one.

- Courtney E. Smith
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Cilla Black "Anyone Who Had A Heart"

It never feels just when someone breaks up with you. Cilla Black, the '60s songstress with the voice of a lion, knows. This song is one to aim right at the head of that mean person who dumped you.

- Courtney E. Smith
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Lorde “Hard Feelings/Loveless,”

No song has better captured the exact somber moment of the breakup, and the way it hangs over you even as you piece your life back together.
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Jewel "Foolish Games"

This is the kind of song that could make a person in any stage of a relationship cry. Jewel conjures up a relationship in its last moments with haunting vividness. "You stood in my doorway, with nothing to say
/ Besides some comment on the weather," she sings. Oh, the awkward coldness that comes once intimacy has left.
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Charlie Puth & Selena Gomez “We Don’t Talk Anymore”

Even after the searing pain of a breakup has dulled, the nagging thoughts of what your ex is doing and who your ex is seeing can still drive a person to slight form of madness. That's just what this song is about.
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Fiona Apple "O' Sailor"

Untrustworthy lovers and unreliable narrators come together in this song about a breakup that she might have instigated or that may have happened to her. But when you're undecided and regretful, this is the song for when you're thinking about what could be instead of what is.
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Taylor Swift "All You Had To Do Was Stay"

In this cinematic song, Swift speaks to someone trying to get back together with her, after he broke up with her. She points out how easy it would've been is to not break up: All he had to do was stay.
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Dolly Parton & Chet Atkins "Do I Ever Cross Your Mind"

This classic country duet may be vintage, but it gets at the universal post-breakup question: Do you relive the past like I do?
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James Arthur "Naked"

This wrenching song is sung from the perspective of someone standing vulnerably before his lover and asking for more, only to be crushed by indifference.
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Toni Braxton "Un-break My Heart"

In which Toni invents an entirely new verb.
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Shakira "Don't Bother"

In this song, Shakira's really angry that this guy is going back to his fiancee. That anger produced one of the best mid-song monologues:

"For you, I'd give up all I own
And move to a communist country
If you came with me, of course
And I'd file my nails so they don't hurt you
And lose those pounds, and learn about football
If it made you stay, but you won't, but you won't"
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Fleetwood Mac "Go Your Own Way"

Stevie Nicks and Lindsay Buckingham set their fights to music. Nicks hated one of the lyrics in particular.

"I very much resented him telling the world that 'packing up, shacking up' with different men was all I wanted to do. He knew it wasn't true. It was just an angry thing that he said. Every time those words would come onstage, I wanted to go over and kill him. He knew it, so he really pushed my buttons through that. It was like, 'I'll make you suffer for leaving me.' And I did," Nicks said.
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A Great Big World and Christina Aguilera "Say Something"

The final conversation before a relationship officially cracks.
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Lauryn Hill "Ex-Factor"

Some relationships aren't cut and dry. This song's about one of them. Even if Hill's separated from her partner, she wants him back — despite knowing it's not the right choice.
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Aly & AJ "Potential Breakup Song"

Need we remind you of the early 2000's best example of a woman demanding good treatment in a relationship?
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Oasis "Don't Look Back in Anger"

It's a breakup song to phases in life.
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Demi Lovato "You Don't Do It For Me Anymore"

Lovato just revealed who this break-up song is about, and it's not her ex Wilmer Valderrama. "You Don't Do It For Me Anymore" is about the old Demi, who was trapped in a cycle of bad habits.
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Mariah Carey "We Belong Together"

Carey strikes the golden balance of ridiculous catchiness and actually moving lyrics.
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Backstreet Boys "Incomplete"

Aside from being a breakup song full of pathos and dramatic boy band vocals, "Incomplete" happens to be the Backstreet Boys' triumphant comeback after a two-year hiatus. Is it a lament? Is a celebration? Must we choose?
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Leonard Cohen "Hey, That's No Way To Say Goodbye"

More than a breakup song, this is a song about a couple facing prolonged separation – perhaps without the possibility of reunion. It's profoundly romantic and will make you cry no matter the stage of a relationship you're in.
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Rod Stewart "Maggie May"

Rod Stewart says it plain: "You broke my heart, and that's what really hurts."
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Fergie "Big Girls Don't Cry"

Will you cry for the song, or for your lost youth in the mid-2000s?
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Gloria Jones "Tainted Love"

Everyone knows the cover of "Tainted Love" made popular by Soft Cell in the '80s, but Gloria Jones Motown version sounds a bit more like a real breakup song.
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Frank Ocean "Thinking Bout You"

With the line, "I've been thinking bout you / do you think about me still?" Frank Ocean reads our break-up ravaged insecurities.
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Natalie Imbruglia "Torn"

In which our favorite '90s singer faces the disintegration of her relationship. Or, more specifically, the disintegration of her idea of the relationship. Disillusionment has never been so catchy.
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The Beatles "Yesterday"

Some things, like the Beatles and Twilight Zone reruns, never get old. "Yesterday" is Paul McCartney at his most stripped-down, mopey, and vulnerable. The brilliance of the line, "Yesterday came suddenly," grows on you.
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Jeff Buckley"Lover You Should've Come Over"

In this aching song, Buckley is mourning a relationship that ended because of his own wishy-washiness. Buckley doesn't know how to stop wanting to be both free and committed. When he sighs, "And maybe i'm too young to keep good love from going wrong," I can't help but tear up — no matter the state of my heart.
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Leona Lewis "Better in Time"

With a blend of hopefulness, nostalgia, and pain, Lewis sings of the light at the end of the breakup tunnel, when she'll be all better — but will still miss her ex.
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Lisa Loeb “Stay (I Missed You)”

Everyone’s favorite bespectacled over-thinker hit on something universal with the line, “I think that I’m throwing, but I’m thrown.” That’s what it’s like being in a bad relationship. The question of “should I stay or should I go?” isn’t always a binary yes-no kind of thing. Sometimes, it sends you down the kind of emotional rabbit hole Loeb goes into here, with winning results.
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Lady Antebellum "Need You Now"

In this unabashed cheese-fest, two exes say to us what they wish they were saying to each other. The couple seems a moment away from getting back together.
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Roxette “It Must Have Been Love”

Immortalized in Pretty Woman, “It Must Have Been Love” represents the perfect ratio of schlock to sentiment. In someone like Celine Dion’s hands, this would have been a complete disaster, but the Swedish duo of Marie Fredriksson and Per Gessle gaze off to “where the water flows” and “where the wind blows” without sounding like ‘90s Disney characters.
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Bob Dylan "If You See Her Say Hello"

Bob Dylan's trying to play it casual in this ballad, but he's dying to hear how his ex is doing.
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Ace of Base “Don’t Turn Around”

Typically, neither crossover reggae hits nor songs by Swedish pop foursomes are known for being particularly sad. (When was the last time Sublime or Abba made you bawl?) For whatever reason, though, this moody summer jam — all about keeping a brave face while having your heart ripped out — has less bounce than a punctured beach ball.
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The Mountain Goats "Woke Up New"

Sung in John Darnielle's gravelly, raw voice, this song perfectly encapsulates the feeling of freedom and deep loneliness that occurs during the days following a breakup. "On the morning when I woke up without you for the first time / I felt free and I felt lonely and I felt scared," the song opens.

The lyrics describe the sense of wandering through daily life with a phantom partner — not there in presence, but there in mind. Darnielle repeats, "What am I gonna do without you?" It's the unanswerable question. He'll do everything he did before, but after waking up new, nothing's the same.

As the lyrics go, "I got ready for the future to arrive." But for now, he's here in the present, and nothing's right at all.
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Lady Gaga "A Million Reasons"

Our Lady Gaga just went through a breakup of her own — she ended an engagement to actor Taylor Kinney while she was writing her newest album Joanne. Fittingly, the album is imbued with both mourning and a come-together rallying cry. The song "Million Reasons" narrates the harrowing decision to dump someone.

"You're giving me a million reasons to let you go," Gaga sings.

But, ultimately, we want to stay no matter what, right? The chorus ends with this unfortunate truth: "Baby, I just need one good one to stay."
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All-American Rejects "Gives You Hell"

The pop-punk hit from 2008 is post-breakup bitching at its best. The refrain — "Hope it gives you hell" — summarizes our most juvenile sentiments toward an ex. It's fun, angsty, and a great song to shout at your ex as they're driving away in their getaway car or whatever.

"Truth be told, I miss you," the All-American Rejects sing. But it's a fake out! They continue, "And truth be told, I'm lyin'!"

The song is one giant, delicious middle finger to exes everywhere, and it's oh-so-satisfying.
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Childish Gambino "Sober"

Gambino (Donald Glover) has always been a melancholy sort, crooning about the trials of the music industry and the perils of existence. "Sober" features CG's plaintive falsetto singing about the need to be inebriated after a breakup.

He sings throughout the track, "And now that it's over, I'll never be sober."

Yup, sounds about right.
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Alicia Keys "If I Ain't Got You"

Alicia Keys was onto something with this track, from her (arguably) greatest album, The Diary of Alicia Keys. The R&B singer was soulful and subtle on this album, and this song's simplicity made it a standout. Also: it was just really fun to sing (albeit offkey).

"Hand me the world on a silver platter, and what good would it be?" she asked. "Someone people want it all / But I don't want nothing at all / If it ain't you baby."
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Rostam "Gravity Don't Pull Me"

You know when the breakup is messy and sad and entirely your fault? Former Vampire Weekend bandmate Rosstam Batmanglij goes solo on this sad breakup track.

"And the worst things I ever did / was to this same boy I couldn't help it," he sings. "I messed things up / And it broke my heart."
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Solomon Burke "Don't Give Up On Me"

The singer famous for "Cry To Me" — you probably know it from Dirty Dancing — makes a true break up song. Soul singer Solomon Burke won a Grammy for the album, which borrows its title from this song.

"Hang in there baby, sooner or later," Burke asks plainly. "I know I'll get it right."
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The Weeknd "Echoes of Silence"

Before the lights and glamour of OVOXO, The Weeknd released Trilogy, an album of his mixtape songs that were floating around the internet. "Echoes of Silence" is one of the weepier tunes: Abel is asking his lover why she insists on hurting them both.

"It's gonna end how you expected girl you're such a masochist and I ask why," Weeknd asks. But the woman is as emotionally ravaged as he is: "And you reply... / I like the thrill / Nothing's gonna make me feel this real." Ouch.
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Otis Redding "These Arms Of Mine"

No one does break up songs better than Otis Redding. "These Arms Of Mine" isn't particularly weepy, but you can hear the longing in Redding's deep voice. "These arms of mine, they are yearning / Yearning from wanting you / And if you would let them hold you / Oh, how grateful I will be," the master of soul sings.

The lyrics are simple — Redding wishes his lover was back in his arms — but the way his voice ascends and drops is deeply moving.
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James Blake Feat. RZA "Take A Fall For Me"

James Blake and RZA play with the push-pull of a relationship that's soured because of a struggle to commit. The song's plot is simple enough: Blake/RZA are men who loved sleeping with a woman that wants more. When she decides to take another man's proposal, their world shatters.

"What will become of me / If I can’t show my love to thee? / What will become of me?" RZA questions, his voice full of regret.
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Mary J. Blige "Not Gon' Cry"

In Waiting To Exhale, this song plays when Angela Bassett is deserted by her cheating husband. It might be the greatest break up song ever — the tempo feels like a desperate whine. MJB always delivers.
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Devendra Banhart "First Song for B"

It's hard to listen to this song without feeling an little bit of an ache. Devendra is in newly in love, and emboldened by it. "I wanna see you be the one who’s first light harbors in the new day / And see you settle into yourself," he sings quietly. "And never be afraid."

But love comes with the inevitable risk of disappointment and distress: "Please destroy me," he begs.
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Al Green “How Can You Mend A Broken Heart”

Is there a song more suited to a particularly steamy, sad night? Is there a song more perfect for a bottle of whiskey and a long scroll through an ex’s engagement album? Al Green’s voice has that soft '70s vibe, and the violins whine and whimper. Here's your late night breakup song.

“How can you mend this broken man? How can a loser ever win?” Green asks, his voice sadly soulful. Somebody please help me mend my broken heart / And let me live again.”
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Kelela "A Message"

Kelela's voice sounds like something that drifted in from another planet. This song opens her EP Hallucinogen, and it sets the tone for the emotional, moody release.

On this track, Kelela sees everything with newfound clarity. She's speaking to an ex-lover, revealing their relationship's hardest truth: she has never satisfied him. A clean break is required. "You don't even see me," she sings, asking, "Are you even breathing?"
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Boyz II Men “End of the Road”

The secret to life is that this is the greatest song ever written. The way it slowly builds from a regular '90s ballad into a hymn of loneliness and sadness is mythic in that uniquely New Jack Swing way. It’s a deeply affecting breakup song but with a kind of the groupthink of wounded machismo: “Why do you play with my heart, why do you play with my mind,” the quartet croons.
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The Smiths “Please, Please, Please Let Me Get What I Want”

For breakups, bad days, and rainy afternoons, there are few groups more perfect than The Smiths. “Please, Please, Please” is gloomy, brooding, and oddly charming all at once. “See the luck I’ve had can make a good man bad,” Morrissey sings.

So what if 500 Days of Summer kind of made The Smiths cool for the Manic Pixie Dream Girl crowd? The song is just so easy to weep to.
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Kelsey Lu “Dreams”

Kelsey Lu’s voice reverberates with a bewitching frequency as she sings about loving a boy that’s bad for her. Lu’s voice drags into a guttural moan that’s deeply moving. “I’m out drinking every night, hoping I’ll run into you,” she sings. “I know you’re no good, but I can’t get enough of you.”

Lu is a new artist and an accomplished cello player. At 18, she ran away to music school and has been growing into an artist to watch since. “Lu gently builds from distant, piercing intensity to something heavy and mournful,” wrote Laura Snapes for Pitchfork.
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Regina Spektor “Samson”

Okay, so you used this song to get over your high school crush. And then you used it to get over your high school boyfriend. And then you used it just on long drives home in college. But this track is one of Regina Spektor’s greatest and most heartbreaking works of art.

The striking imagery — cutting a lover’s hair with blunt scissors, kissing in the morning light — is still there, and still just as moving. But Spektor also gets at a moving truth most sad love songs don’t talk about: “The history books forgot about us and the Bible didn't mention us, not even once.”
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Nina Simone “Ne Me Quitte Pas”

For starters, the title is French for “Don’t Leave Me.” But you don’t have to understand another language to feel the deep unrest in Simone’s soul on this song. Simone — a truly distinct and talented vocalist (and concert pianist) — mourns her love, offering him rain and earth and everything in between. She’ll hide herself in his shadow after being rejected. “I will dig the earth / Until after my death / To cover your body / With gold and light.” Maybe don’t look up the French translation. Simone’s voice is enough to echo through your heart’s caverns.
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Bon Iver "Skinny Love"

Bon Iver, a.k.a. Justin Vernon, once told Pitchfork that "Skinny Love" is about when "you're in a relationship because you need help, but that's not necessarily why you should be in a relationship." That anguish fills every note of this plaintive song. By the time Vernon wails, "And now all your love is wasted/ And then who the hell was I?" You'll want to cry out along with him. Also, if Vernon's notoriously bad enunciation means you can't really understand what he's saying, there's always the beautiful Birdy cover.
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Lucy Rose "Shiver"

We first got wind of Rose's sweetly melancholy tune when it was employed during the Adam-Hannah split in season 4 of Girls. Since then, it's been a go-to for when we're feeling weepy. Rose doesn't place the blame on her romantic partner for the split; she admits responsibility. But even though the breakup was mutual, she remains nostalgic for the good moments. "Shiver" is the perfect song for when you know you need to move on, but just can't.
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Joni Mitchell "A Case Of You"

Joni Mitchell's conversational, devastating song, describes what it's like when a relationship is over but a connection to another person remains. "You're in my blood like holy wine/ You taste so bitter and so sweet," she sings. There are plenty of songs on Blue that will do the trick if you're looking to wallow, but "A Case Of You" articulates what it's like to a lose someone who has burrowed into your soul.
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Adele “Someone Like You”

There’s a war going down inside Adele’s head. She wants her ex to be happy, and yet she finds herself wandering past his flat, hoping he’ll see her, remember the good times, and forget all about his new girl, who happens to be his wife. “Never mind, I’ll find someone like you,” she sings, though she, like Sinead, knows that nothing compares.
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Bonnie Raitt “I Can’t Make You Love Me”

Is it a breakup song if the people in question are still sharing a bed? In this all-time soul-crusher, the intimacy is purely physical, and as unfulfilling as that is, Bonnie will take it — for a little bit longer. “Morning will come and I'll do what's right / Just give me till then to give up this fight,” she sings, working up the strength to walk away. “And I will give up this fight.”
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Sinead O’Connor “Nothing Compares 2U”

If you know the exact amount of time that’s elapsed since you got dumped, you’re in deep trouble. On this Prince-penned classic, we meet Sinead “seven hours and 15 days” after her love took a hike, and she’s still reeling. She’s even been to the see the doctor. Doc's advice: Have some fun. Even in Ireland, the health-care system is whack.
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Jay Z “Song Cry”

Rappers have feelings, too. The thing about Jay is that he has trouble showing his, so in lieu of shedding actual tears, he aims to “make this song cry.” He does a decent job, though even as he opens his heart and apologizes to the girl he cheated on, he doesn’t quite ditch the macho posturing that might have made this tender mea culpa ring truer.
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The Cure “Pictures of You”

Robert Smith has been writing intensely personal, moody songs of heartbreak pretty much since he founded The Cure in 1976. But this one is the most beautiful. Almost eight minutes long, "Pictures of You" finds Smith reflecting on memories of a person he loved, triggered by old photographs. “Remembering you falling into my arms / Crying for the death of your heart / You were stone white, so delicate, lost in the cold,” he sings. “You were always so lost in the dark.” For a Goth boy who is still married to his high school sweetheart, he sure knows how to capture the pain of lost love.
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Roy Orbison “Crying”

There’s nothing worse than bumping into your ex and having to pretend you’re not a total whimpering mess. Roy figures he pulls it off — “You couldn’t tell that I’d been crying” — and if he does, he’s a hell of an actor. In that signature opera-billy style of his, Orbison sings with a hurt not easily hidden.
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The Beach Boys “Caroline, No”

Originally titled “Carol, I Know,” this song became infinitely better when Brian Wilson misunderstood collaborator Tony Asher’s initial reading of the lyrics. The narrator in this song doesn’t know Jack. “Where did your long hair go?” he asks. “Where is the girl I used to know?” “Could I ever find in you again things that made me love you so much then?” If the bummed-out orch-pop backing is any indication, the answers to that last question is “Brian, no.”
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Beck “Lost Cause”

Arguably the saddest song on Beck’s saddest album, this is the slow, strummy equivalent of waving a white flag. Poor Beck knows there’s nothing he can do to save this girl from herself, so he’s pulling his forces and signing whatever treaty he needs in order to escape with his sanity.
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The Postal Service “Nothing Better”

Selective memory is a the worst. The male character in this synth-pop duet figures there’d be nothing sweeter than marrying the girl who’s recently left him. Unfortunately, she’s prepared charts and graphs to remind him of why the good times weren’t that good. This is young love in the time of Excel.
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Everything But the Girl “The Heart Remains A Child”

In this song, vocalist Tracey Thorn bluntly asks a question that occurs too often during heartbreak: "Why don't you love me?" If that seems like a simplistic inquiry, well, that's sort of the point. This song perfectly expresses how we regress after heartbreak, and fall into our same, mopey patterns.
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Rihanna ft. Mikky Ekko “Stay”

Rih clears a little path through a hoarder’s den of messy feelings on this confusing piano ballad. “Not really sure how I feel about it,” she confesses, right before her duet partner, Mikky Ekko, sings the same line. These are two people who are completely wrong for each other, and when they join their voices on the line “funny, you’re the broken one, but I’m the only one who needed saving,” it’s like they’re both dishing blame and seeking salvation at the same time.
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Janet Jackson “Come Back To Me”

Ugh, that feeling when the breakup has come and gone and you're STILL not over it! Janet's mournful lament on her abandonded heart will rip yours open all over again.
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Diana Krall “Almost Blue”

“There’s a girl here and she’s almost you,” Diana Krall sings in her cover of her husband Elvis Costello's '80s single about infidelity and exhaustion. It is one chilly-ass torch song from a very dark place.
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Kanye West “Heartless”

At the risk of being melodramatic, Kanye dubs this “the coldest story ever told.” It’s the tale of two former lovers — presumably Yeezy and former fiancée, Alexis Phifer — who’ve wronged each other and wound up bitter enemies. “How could you be so Dr. Evil?” he raps, too mentally spent to muster anything better than an Austin Powers joke.
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Weezer "Say It Ain't So”

Rivers Cuomo wrote this song about his parents fighting and getting divorced — and the alcoholism that tipped him off that the storm was coming. It's also a lament from a kid on causing the divorce. All in all, a real heartbreaker.
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Whitney Houston “I Will Always Love You”

That towering, thunderous, ground-shaking “And I…” high note Whitney hits toward the end of this monster ballad makes total sense. Written by Dolly Parton, this is one of the most selfless love songs of all time, and before taking her leave of the man she knows she’s holding back, Whitney gets in one last show of dignity: an extended vowel sound people will be talking about until the end of time.
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Carole King “It’s Too Late”

It’s the sense of finality that makes this 1971 chart-topper such a killer. “Something inside has died, and I can’t hide it,” King sings, a little sad, a little relieved to no longer have to carry on a charade. “And I just can’t fake it.”
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No Doubt “Don’t Speak”

Success must have been bittersweet for Gwen Stefani and Tony Kanal, punk-ska’s answer to Stevie Nicks and Lindsey Buckingham. No Doubt’s breakthrough 1996 single (and lone No. 1) is all about their breakup — an emotional earthquake Gwen clearly hadn’t recovered from the day she cut this vocal.
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Elvis Presley “Are You Lonesome Tonight”

In the famous spoken-word part, a truly miserable-sounding Elvis looks back on a failed relationship like a theater critic reviewing a play. Act one was great. Act two: not so much. Looking ahead to the act three, Elvis is only willing to entertain one possible ending. “If you won't come back to me,” he says, “then make them bring the curtain down.”
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Amy Winehouse “Back to Black”

The references to “puff” and “blow” give this an air of druggy self-destruction that heightens the sadness, especially in light of Amy’s untimely death. Even without those lines, though, it’s a heavy song — a smoldering James Bond theme for an everyday story about a woman plummeting into darkness as her man goes back to his former girlfriend.
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Madonna "Take a Bow"

Taking a page out of the King's playbook, Madonna uses theater as a metaphor for her latest heartbreak. "You deserve an award for the role that you played," she tells the deceptive lover she's finally wriggled free from. "No more masquerade." Given that Madge used to be married to Sean Penn, the lesson here may be to only date crummy actors. Their lies are easier to spot.
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