The Best Break-Up Songs Of All Time

Every single one of us has been there before: The heart-wrenching sadness, the possibility of never smiling again – an unending, overdramatic burn. Yep, we are talking about heartache. But out of great pain comes even better art, and there may be nothing as powerful as the wallowing, soul-soothing balm of the break-up song.
Even if you aren't currently splitting up, a true tribute to the pain of heartache always sounds great (especially on a Monday, areweright?), and these songs are simply the crème de la crème of anthems dedicated to the demise of romance. And because just listing these gems from the depth isn't enough, we've added our own memories and reflections to each of these picks. Because sometimes, before picking yourself up, dusting off and moving on can occur, we all need a good, Eeyore-style pity session for therapy's sake.
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Once you've reminisced over lost love, cheer up with our ultimate going-out playlist. Trust us, you are gonna need it.
Can anyone pass a tissue?
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Photo: Courtesy of Atlantic Records.


"The earnest longing, and disassociation with reality — that weird sensation of floating through time and space — is enough to get lost in for four and a half minutes." — Hayden Manders, editorial assistant
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Photo: Courtesy of Chrysalis Records Ltd..


"Yes, 'Nothing Compares 2 U' is a gorgeous cover, but it is about trying to get back with someone, not shutting the door on a part of your life. I loved this song since before I even knew what the word 'acquaintance' meant, but it was only as an adult that the power, sadness, and fortitude expressed in this song was jaw dropping. Have you ever heard an acoustic guitar sound so angry? This is *the* break-up anthem, and you can disagree with me, but you'd be wrong." — Leila Brillson, senior news editor
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Photo: Courtesy of Zero Summer.


"After ending a nearly four-year relationship, I made the very difficult decision to end things. This song is the anthem for "you'll be okay," and reminds you to just breathe. It also doubles as excellent yoga music, if you're into it."— Vanessa Golembewski, editorial assistant
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Photo: Courtesy of Warner Bros.


"I once dated a boy who hated this BEAUTIFUL, heart-wrenching song because he claimed it "had no bridge." He was stupid, and Morrissey is everything. Needless to say, that relationship didn't last very long." — Vanessa Golembewski, editorial assistant
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Photo: Courtesy of Saddle Creek Records.


"I spent about a year dating a girl with drug problems. It was really hard to break up with her because, you know, addictions are complicated. I listened to this song on repeat and cried, a lot. The line 'I was afraid to be alone, now I'm scared that's how I'd like to be' really resonated." — Gabrielle Korn, beauty assistant
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Photo: Courtesy of Essential Media Group.


"A country cover of the Roy Orbison song 'Crying', which originally debuted in 1961. Lame, but it gets me every time." — Tara Rasmus, assistant beauty editor
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Photo: Courtesy of Lykke Li.


"Haunting, raw, and completely cathartic, Lykke Li's lament over a lover leaving doesn't hesitate to explore the loss of identity that comes with breakup." — Hayden Manders, editorial assistant
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Photo: Courtesy of Universal Records Inc..


"There was a point in time when I listened to this, Joanna Newsome's 'Peach, Plum, Pear' (note: this is another devastating song but not on Spotify) and Paul Simon's '50 Ways To Leave Your Lover' religiously for about three months straight. Nico's voice is super haunting, as are the words of the song. The final bit is what really gets me 'please don't confront me with my failures... I have not forgotten them.' Indeed, how could I forget, as I'm sobbing in my car?" — Annie Georgia Greenberg, New York editor
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Photo: Courtesy of XL Recordings Ltd.


"There may have been a period when I walked around the streets of Manhattan quietly crying to Adele's 'Don't You Remember.' Because really, doesn't he remember? WTF?" — Neha Gandhi, deputy editor
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Photo: Courtesy of Matador Records.


"The song starts, 'Once I wanted to be the greatest (greatest, greatest, greatest).' It begins with defeat and ends with defeat for when you're really feeling, well, defeated." — Annie Georgia Greenberg, New York editor
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Photo: Courtesy of Quarterstick Records.


"I once dated someone who said this instrumental was sad. I said it was beautiful. We were definitely wrong for each other, but we were both right about this song." — Annie Tomlin, beauty director
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Photo: Courtesy of Domino Recording Co.


"What's better to wallow in than a swelling piano melody? Nothing." — Hayden Manders, editorial assistant
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Photo: Courtesy of Interscope Records.


"I don't get weepy during breakups. I get angry." — Christopher Michael Beer, video editor
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Photo: Courtesy of Geffen Records.


"The greatness of 'Dammit' can be distilled to the seeing-your-ex-on-another-date vignette that makes up the chorus: 'And I'll smile, and you'll wave / We'll pretend it's OK.' Perfectly nostalgic, supremely depressing." — Nathan Reese, contributing editor
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Photo: Courtesy of Music Entertainment Inc.


"Even Fiona Apple’s breathy love ballads sound like breakup songs, so her somewhat-slurred vocals on 'Shadowboxer' make the song sound like something she should be singing while perched atop a piano in a 1920’s prohibition-era speakeasy. And the lyrics? — 'So I'll be sure to/ Stay wary of you, love/ To save the pain of/ Once my flame and/ Twice my burn' — yeah, she’s a lover scorned, indeed." — Lauren Caruso, staff writer
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Photo: Courtesy of BMG Entertainment.


"I've never actually played this during a breakup, but it is a soulful lament that never fails to affect, regardless of your current situation. A timeless tune, with a couple of lyrical switches, perfectly rendered by one of the world's greatest singers. Also, comparing someone to "bad brandy wine" should definitely be reintroduced into the popular vernacular." — Lexi Nisita, news editor
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Photo: Courtesy of Sony Music Entertainment Ltd.


"An old boyfriend — whom I loved and who didn't love me back — turned me on to this song. The chorus just makes me stop in my tracks: 'Here comes the blue skies, here comes springtime...' It just makes me feel like everything will be okay." — Susan Kaplow, editorial director.
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Photo: Courtesy of Roc-A-Fella Records.


"Before Kanye was a leather-clad industrial punk, he was just a sad dude trying to get over an ex. For better or worse, this song is pretty much responsible for Drake, The Weeknd, and all the heartfelt hip-hop that's dominated the charts for the past few years." — Nathan Reese, contributing editor
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Photo: Courtesy of Sony Music Entertainment Inc.


"Worst break-up ever: Junior year of high school, walking to school with my Discman in my hoodie's pouch, smoking cigarettes through fingerless gloves, committing Lauryn Hill's verse to memory. 'Pain suppressed, will lead to cardiac arrest/Diamonds deserve diamonds, but he convinced me I was worth less.' One of the most powerful moments on a powerful album." — Leila Brillson, senior news editor
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Photo: Courtesy of Saddle Creek Records.


"First of all, I am not currently accepting any negative feedback about Bright Eyes and/or Conor Oberst. Second of all, this song is great if you really just want to indulge how sad and miserable and pathetic and awful you are. Not exactly uplifting, but it captures the pain of wanting an impossibly perfect relationship and knowing you'll never achieve that." — Lexi Nisita, news editor
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Photo: Courtesy of Arista Records, Inc.


"It's so dramatic. It's so powerful. And it totally indulges those most desperate, secret feelings that maybe you really do have nothing in the absence of this relationship. You're left with nothing. You don't have the energy to start over. You'll never do better. It's ALL over. And you have NOTHING." — Neha Gandhi, deputy editor
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Photo: Courtesy of Sony Music Entertainment.


"This song came out right when my then-boyfriend of five years and I were going through a rough patch, and when Maxwell himself explained that it was about meeting the right girl at the wrong time, I’m pretty sure I cried for two weeks straight. The warm, soulful ode still gets me every time." — Lauren Caruso, staff writer
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Photo: Courtesy of The Island Def Jam Music Group.


"Frank Ocean's opus about a doomed relationship that starts at Coachella and ends with our hero completely numb. It's a California romance that moves from blissed-out love and drugged-out last dregs without missing a beat." — Nathan Reese, contributing editor
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Photo: Courtesy of BMG Music.


"If you own a gun or have a lot of prescription pills around, I strongly suggest handing them over to trusted friends before playing this song — it's the living worst. Written by Marvin Moore and George Campbell, Reeves' sweet, warm chart-topping version from 1957 captures that moment of absolute, abject, weeping-in-my-room-with-a-carton-of-cigs loneliness so perfectly, you'll feel claustrophobic wherever you hear it. Feeling sorry for yourself has a theme song, and it's country." — Gabriel Bell, staff writer
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Photo: Courtesy of Merge Records.


"This entire album is pretty epic, especially when listened to in one sitting (see: "Neighborhood #2," "Every Time I Close My Eyes (Lies!)." This one's bittersweet for me because it reminds me of high school (and my high school sweetheart). The whole idea of building tunnels to be together in this distilled magical world that's so obviously not the real world is what really jerks my tears, here. The song speaks to the energy and effort and willingness it takes to be in a relationship. Plus, it pulled double duty for my multiple long distance relationships that followed." — Annie Georgia Greenberg, New York editor
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Photo: Courtesy of Warner Bros.


"Actually, Rumours is an epic break-up album about one of rock's most notorious break-ups. In an entire album about ending a relationship, this one suddenly turns your heartache into a dance party. Which is the best type of break-up ever." — Leila Brillson, senior news editor
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Photo: Courtesy of Saddle Creek Records.


"The ultimate tale of doomed high-school romance told through Connor Oberst's unparalleled quavering voice. 'You are my sunshine' never sounded so bleak." — Nathan Reese, contributing editor
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Photo: Courtesy of Legacy Recordings.


"This isn't my story, but my mom once told me this helped her get through her divorce. It's such a happy song, but with such sad lyrics." — Leila Brillson, senior news editor
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Photo: Courtesy of ASTRALWERKS.


"Though our relationship only lasted for the summer of 2009, my relationship with Six Feet Under was technically five seasons long. Once it was over, I went through a solid four-week phase in which I would cry every time I heard Sia's 'Breathe Me," partially because it was the soundtrack to the final moments of the series finale, and partially because that song is just really freaking sad. What, you can't be in a relationship with a TV show?" — Vanessa Golembewski, editorial assistant
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Photo: Courtesy of Interscope/Cherrytree.


"Goulding's Halcyon album was the breakup album of the last year, but her airy, hesitant delivery of the verse, 'I'm exhausted with loving / No fight in me / I'm defeated / I know I'm fooled / I can't help it / You make my heart so helpless' hangs in the air well after the track is finished." — Hayden Manders, editorial assistant
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Photo: Courtesy of Sub Pop Records.


"Not a breakup song, per say, but 'No One’s Gonna Love You' totally belongs on the soundtrack for sad, rainy Sundays. Trust: It’ll make you feel all the feelings." — Lauren Caruso, staff writer
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Photo: Courtesy of Konichiwa Records.


"Because, duh." — Us
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Designed by Isabelle Rancier.


The playlist, for your pleasure.
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