A Dozen Epic Breakup Albums

Breaking up is hard to do.

I’ve been on both sides of it – the dude callously letting someone down, the guy left standing in the rain.  It ain’t any fun, no matter what side of the fence you stand on when it all goes to shit.  Love leaves its scars, and I surely have my share.  Looking back, you try to suck whatever marrow is left off the breakup carcass, but you find mostly gristle – heart and teeth-breaking bone left in the wake of something that – at least for a little while – was truly something to savor.

I’ve written my share of breakup songs, sitting at the piano in the dark, lost and confused.  My most recent album was a potpourri of tunes about the woman I discarded after a quickie ‘that-was-a-mistake’ marriage and the woman who I put my faith in and my best foot forward with who would wind up betraying me more than once.  It was a rough stretch that’s finally in the rearview, and music was my medicine (see also: running and writing).  In spite of it all, I can still feel the love inside me – the tug of those romantic heartstrings is a rare thing these days, but it’s there (unless I’m having a heart attack?).

Is loving and losing my inherent nature?  Is it a curse?  Is it my destiny?  Is it me?  Is it them?  I do not know.

What I do know is that I am not alone – as a major league music fan, I’ve often curled up with my dog, a pair of headphones and a bottle of whiskey, letting the heartbreak of others numb me, reminding me that we’re all flawed, we’re all rubes, and that the more we give of ourselves, the more that can be taken away.  But you can’t give up.  All you can do is try your best and have a little faith.  Seems the worst than can happen is that you’ll have plenty of material for your next record.

With all due respect to Bob Dylan, Taylor Swift and Yeezus, here’s a dozen of the most poignant breakup albums I’ve had the pleasure of absorbing.

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Beck – Sea Change (2002)

Beck Hansen’s eighth studio album was a major league curve ball, and also the soundtrack to my life in late 2002, a year in which I ended a 6+ year relationship.  To date, it’s still the hardest breakup of my life and the longest love that led up to it.  The dude who wrote “Loser” and “Devil’s Haircut” shocked the world with Sea Change, inspired by the end of his own 8+ year relationship.  Sincerity and sorrow replaced goofy lyrics and funky samples and the results were undeniable – this wasn’t just a great Beck album, this was one of the greatest albums of the decade, now widely revered as a classic.

The contributions of Eternal Sunshine of the Spotless Mind composer Jon Brion (who would collaborate with Beck on the great “Everybody’s Gotta Learn Sometime” from that film’s soundtrack) and Beck’s father on string arrangements (he would do it again on the Grammy Award-winning, but not-as-good Morning Phase) effectively add to the melancholy.

I saw Beck perform many songs from Sea Change in New York City with The Flaming Lips as his backing band.  I took the next girl who I would eventually call my girlfriend.  It was one of the best – and most bittersweet – concert experiences of my life.


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Carole King – Tapestry (1971)

Carole King was the Adele of the ’70s, her sophomore album rife with radio hits, including the #1 “It’s Too Late,” one of music’s most legendary breakup songs.  The album won 4 Grammys and sold over 10 million copies, and while it’s not all lamentation and regret, the bummer songs are undeniable, including the long-distance runaround of “So Far Away” and King’s cover of The Shirelle’s “Will You Love Me Tomorrow?” (which became iconic over a decade later when featured on the nostalgic TV show The Wonder Years).

Add the fact that King co-wrote a number of songs with her ex-husband, and that the lyrics from “It’s Too Late” were written by Toni Stern in response to her breakup with James Taylor, who is heavily featured on the album – and would cover King’s “You Got A Friend” on his own album, and you have one helluva tapestry indeed.

Bonus Bummer:  I spelled the word “tapestry” wrong during the district spelling bee when I was in 5th grade and wound up crying in a public school bathroom, having no knowledge of this album’s existence.


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Adele – 21 (2011)

Unless you’ve been sleeping under a rock, you’ve heard about this album and its legacy.  You’ve heard “Rolling In The Deep” and “Set Fire To The Rain” a thousand times and you still get it.  Like the rest of civilization, you’re drinking the Adele Kool-Aid.  Its bittersweet deliciousness is undeniable.  Rumour has it (*cough cough*) that Adele was going for a more upbeat sound on this album than on her Soul-inspired throwback debut, and it wasn’t until her relationship started falling apart that 21 took shape.

I’ve had the displeasure of being in a relationship in which I was writing songs about things going wrong while still in said relationship, and clearly Adele can relate.  The confessional “Take It All” was supposedly the catalyst for the romantic separation that followed, and the subsequent catapult of young Adele into the musical stratosphere.  Take this crumbling fool with you.


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Fleetwood Mac – Rumours (1977)

The backstory of Rumours is the stuff of legend, what with every single member of the five-piece band entangled in romantic drama – with each other! – during its creation.  John & Christine divorce, Lindsay and Stevie break up, Mick’s wife cheats on him, Stevie shacks up with Mick.  You can’t make this stuff up.

The result, of course, is one of the greatest albums of all-time, and 1978’s Album of the Year.  I can vividly remember hearing Rumours for the first time at my uncle’s house when I was 5 years old – it’s one of my earliest memories of music.  My favorite song on the album, “The Chain” is, ironically, the only song on which the band collaborated as a whole, where more cutting tunes like Lindsay Buckingham’s “Go Your Own Way” and “Secondhand News” were not-so-subtle messages delivered by the offended party to the other members in the form of song.


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Tobias Jesso Jr. – Goon (2015)

Relative unknown Canadian singer/songwriter Tobias Jesso Jr. has collaborated with Sia, Haim, and the aforementioned Adele, but his debut solo album is a revelation, reminiscent of Randy Newman and one of my faves, the late, great Harry Nilsson.  Recorded in the wake of a romantic breakup and his mother’s battle with cancer, Jesso’s pining baroque pop shines on songs like “How Could You Babe” and the simple and beautiful “Can’t Stop Thinking About You.”

There’s a refreshing simplicity to the arrangements, making bits of the heart-wrenching material sound almost cheerful.  No word on a follow-up, but it will be hard for Jesso to top Goon.


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Bon Iver – For Emma, Forever Ago (2007)

Justin Vernon’s sojourn to a remote cabin in Wisconsin is Walden-esque, only instead of a book, a critically-acclaimed debut album was produced, putting Vernon and the label that signed him on the map.  Written and recorded in near-desolate isolation after Vernon’s breakup with his band mates and then his girlfriend (been there, done that…tho I skipped the killing deer and fending off bears in a cabin part), Bon Iver’s emergence is an almost not-so-happy accident.  It’s the soundtrack to a guy giving up on the mediocrity of his life and desperately attempting a do-over.

The album is rife with angelic falsetto harmonies and vague references to Vernon’s relationship, especially effective on the painfully beautiful “Skinny Love.”  Bon Iver would reach greater heights on subsequent releases, but For Emma‘s stark and startling compositions are what got the snowball rolling.


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Death Cab For Cutie – Transatlanticism (2003)

Death Cab’s second album is still their truest, and it’s all right there in the title, a reference to long-distance emotional longing, about the practicalities that interfere with romance’s unlikely possibilities.  I’ve been there, the naive fool who believed that any obstacle could be overcome by love, only to have his passion balloon quickly burst.

Transatlanticism is rife with indie emo conceit, and it’s not necessarily the genre’s touchstone achievement, but “The New Year” and “Coney Island,” in particular, still resonate.  The refrain of the epic title track – “I need you so much closer” – doesn’t necessarily refer to geographical distance. I was in a dark place when this album came out, a very transitional period of my life, which now all seems like a pittance in consideration of everything that has happened after it came out, but for a short period of time, Ben Gibbard was a storytelling god.


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Portishead – Dummy (1994)

I’ll forgive Portishead for unwittingly popularizing trip-hop, but I can’t forgive them for providing the score to my awkward teenage years, an age dominated by confusing rejection and unavoidable insecurity.

I remember hearing Dummy for the first time while laying on the floor – of my best friend’s sister’s room.  I was on the floor because the bed was occupied – she was in it with her best friend, a girl who I had dated briefly and still had a major crush on.  In darkness, I lay there wishing I had traded places with my best friend’s sister – that it was I laying in bed with my fantasy girl while Beth Gibbons complained that nobody loved her.  At the time, breakbeat-tinged rejection never made me feel so blue.  Nobody loves me…..it’s true.


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Bjork – Homogenic (1997)

Iceland’s Bjork is undeniably an acquired taste, the infamous “Swan Dress” still, unfortunately, her defining moment of notoriety (just Google ‘swan dress’ if you don’t believe me).  But her early albums are a thrill of wonder and ambient noise.  On her third album, Bjork ups the ante with more thoughtful, atmospheric arrangements, superior electronic drum production, and a hopeful coda in the gorgeous “All Is Full Of Love.”

‘Hopeful’ is a surprise, considering the backstory of Bjork’s life leading up to Homogenic is almost too crazy to be believed.  It involves her breakup with UK musician Goldie and a real-life stalker who would ultimately kill himself over his obsession with the singer.


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The Cure – Disintegration (1989)

I was late to the party when it came to The Cure, one of those acts that I didn’t quite get at first.  My initial exposure to the band was 1992’s Wish, and I found its poppy optimism cheesy and singer Robert Smith’s Edward Scissorhands-wannabe look off-putting.  “Friday I’m In Love”?  Blecch.  Then I listened to Disintegration and quickly rethought my stance.

The album isn’t influenced by any particular breakup – the linchpins “Lovesong” and “Pictures Of You” are actually inspired by Smith’s then-fiancee. It’s Smith’s disillusionment with his status in life right before turning 30 (*sigh* Millennials) that sets the mood.  But the glorious doom and gloom that dominates the album cannot be ignored – put this on during a rainy day after a breakup, and you will get the desired effect.  Disintegration is The Cure at their finest – and one of the best albums of the 1980s.


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Ryan Adams – Heartbreaker (2000)

You could fill this entire list with Ryan Adams albums and still have a couple left over, but it all started with Heartbreaker, his solo debut after time in the trenches with alt-country act Whiskeytown.  Adams often sojourns into alt-country territory on his solo albums, as well, which is why I’ve never been more than a casual fan (see also: Wilco), but the subject matter of most of his work is surely something I can also relate to (he was also born 4 days before me, so there’s that).

Adams famously covered Taylor Swift’s 1989 album song-for-song after his divorce from Mandy Moore, but Heartbreaker is that album’s reserved drunken grandfather, a quiet and desolate journey through a much-younger man’s psyche after breaking up with his music publicist girlfriend.  It contains moments of introspective and desperate beauty that present the argument that the more one fucks up romantically, the more special their music tends to be.  Adams’ reception is generally divisive, but those who enjoy him do so rabidly, and one can understand why when listening to this album.


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Amy Winehouse – Back To Black (2006)

One of the great contemporary R&B albums is somewhat marred by the inclusion of the mega-hit “Rehab,” which flooded commercial radio and hit you over the head with a sledgehammer, partially obscuring the beauty of the rest of Back To Black.  The album serves as Winehouse’s confessional as an abusive relationship with her hanger-on boyfriend spirals down and out, along with Amy herself, who would be gone soon after the album’s critical and commercial success.

I didn’t take to Winehouse at first, witnessing her embarrassing alcohol-and-heroin-fueled public appearances before attending to her music, but the affecting documentary Amy changed my mind.  It’s a must-see, and an affirmation of Winehouse’s true talent, all while fighting off various demons, and ultimately succumbing to them.  One could argue that there would be no Adele without Amy, and every listen to the affecting title track and “Love Is A Losing Game” only strengthens that argument.