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.
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.
"Shiver," Lucy Rose
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.
"A Case Of You," Joni Mitchell
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.
Photo: Courtesy of Warner Bros. Records.
“Someone Like You,” Adele
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.
Photo: Courtesy of XL Recordings/Columbia.
“Love Is Stronger Than Pride,” Sade
Pride vs. love is like your JV high school basketball team vs. the 2012-13 Miami Heat. Sade knows all about the mismatch, and while she wishes she could hate this guy who's wrecked her life, the affection she feels is quick and tenacious, like the triumvirate of LeBron James, Chris Bosh, and Dwayne Wade. All she can do is run out the clock and hope to rebuild next season.
Photo: Courtesy of Sony.
“I Can’t Make You Love Me,” Bonnie Raitt
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.”
Photo: Courtesy of Capitol.
“Nothing Compares 2 U,” Sinead O’Connor
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.
Photo: Courtesy of Parlophone.
“Song Cry,” Jay-Z
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.
Photo: Courtesy of Roc-a-Fella Records.
“Pictures of You,” The Cure
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.
Photo: Courtesy of Elektra.
“Crying,” Roy Orbison
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.
Photo: Courtesy of WAX TIME.
“Caroline, No,” The Beach Boys
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.”
Photo: Courtesy of Capitol.
“You’ve Got to Hide Your Love Away,” The Beatles
Everyone tells John Lennon he should suppress his feelings and go about his business, but this guy’s business was expressing his feelings. They come through in a big way on this transitional Beatles cut.
Photo: Courtesy of Capitol.
“Lost Cause,” Beck
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.
Photo: Courtesy of Interscope.
“Nothing Better,” The Postal Service
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.
Photo: Courtesy of Sub-Pop Records.
“You Left Me Standing In the Doorway,” Bob Dylan
Dylan waited until he was 56 to write one of the best lines of his career: “Don’t know if I saw you, if I would kiss you or kill you.” That, like the title, pretty much says it all, but then he goes one better: “It probably wouldn’t matter to you anyhow.” It’s a rascally line from a guy who’s wicked bummed but still pretty feisty.
Photo: Courtesy of Columbia.
“The Heart Remains A Child,” Everything But the Girl
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.
Photo: Courtesy of Virgin Records.
“Stay,” Rihanna ft. Mikky Ekko
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.
Photo: Courtesy of ISLAND-DEF JAM.
“Again,” Janet Jackson
When Janet hears her former boo is back in town, she goes off on a soul-searching journey that begins with wishful thinking (“I’ll never fall in love with you again”) and ends with acceptance (“God knows I do love you again”). The single-word title may be a predictor of how this story ends.
Photo: Courtesy of Virgin Records.
“Almost Blue,” Elvis Costello
“There’s a girl here and she’s almost you,” Elvis sings, weary like a lounge singer playing to a roomful of 2 a.m. drunks. He’s found a new romance that leaves him a little cold — “almost blue” — and that makes for one chilly-ass torch song.
Photo: Courtesy of Hip-O Records.
“Heartless,” Kanye West
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.
Photo: Courtesy of Roc-A-Fella Records.
“You Were Meant for Me,” Jewel
If you ask Parks and Recreation protagonist Leslie Knope, there are few problems that can’t be solved by breakfast foods. Jewel might beg to differ. “I got my eggs, I got my pancakes too / I got my maple syrup, everything but you,” she sings, unwilling to accept her sugary a.m. feast as a substitute for the one that got away. Eventually, Jewel tells herself, he’ll realize they’re meant for each other. Until then, Mrs. Butterworth will have to pick up the slack.
Photo: Courtesy of Atlantic.
"The World Has Turned and Left Me Here,” Weezer
Rivers Cuomo has it even worse than Robert Smith does in “Pictures of You.” On this Blue Album gem, the Weezer frontman is talking to wallet photos and losing his grip on reality. “You laughed, enchanted by my intellect,” he sings to his ex. “Or maybe you didn't.” Either way, he won’t be adding any more smiley snapshots of this girl to his plastic sheath.
Photo: Courtesy of Geffen.
“I Will Always Love You,” Whitney Houston
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.
Photo: Courtesy of Sony Music Entertainment.
“It’s Too Late,” Carole King
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.”
Photo: Courtesy of Sony.
“Don’t Speak,” No Doubt
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.
Photo: Courtesy of Interscope.
“Are You Lonesome Tonight,” Elvis Presley
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.”
Photo: Courtesy of RCA.
“Without You,” Mariah Carey
Talk about fresh wounds. “I can’t forget this evening, or your face as you were leaving,” sings Mariah, who’s coming to us mere hours after the breakup went down. She hasn’t had time to process things, so she’s feeling a little overdramatic. Hence that chorus: a show-stopping declaration of why life is no longer livable. In time, she’ll get over it, but for now, let her wail.
Photo: Courtesy of Sony.
“Back to Black,” Amy Winehouse
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.
Photo: Courtesy of Universal Republic.
"Take a Bow," Madonna
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.
Photo: Courtesy of Sire/London/Rhino.
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