All the tracks lead you to heartbreak.

November 19, 2009 1:26 PM

Best break up albums of all time?

So, I recently went through a heart-rending breakup. In which I have listened to so many breakup songs (We Belong Together! The End of the Road! Martha by Tom Waits!) and that This American Life episode called "Break Up" so many times on repeat, singing along with clenched fists that the neighbors may call the state on me. I just purchased The Fall by Norah Jones, which may be the perfect breakup album (if you like Norah Jones, and I do!), which is a back-and-forth chronicle of ambivalence and heartbreak over her own break up with former collaborator/producer/boyfriend Lee Alexander. There's lots of threads about break up songs. But what about break up albums? I'm only coming up with recent examples like Alanis Morissette's "Flavors of Entanglement," about her breakup with Ryan Reynolds. And then there's Liz Phair's "Exile in Guyville." But tell me, MeFites, what are some others? I've been loving just immersing myself in one album that says it all: "I need you, come back, fuck off, you suck."

posted by dhn to media & arts (103 comments total)

Bon Iver, For Emma, Forever Ago
posted by meerkatty at 1:29 PM on November 19, 2009 [2 favorites]

Sarah Harmer's "You Were Here" is probably my favourite break-up album.

Bob Dylan's "Blood on the Tracks" is a pretty popular one too.
posted by backwards guitar at 1:30 PM on November 19, 2009

The The - Mind Bomb. It's not ALL, or even mostly, breakup, but what is is just killer.
posted by dirtdirt at 1:30 PM on November 19, 2009

Was recently hanging with a friend who is over a decade my junior (who had recently ended a long relationship) and he too knew the appropriateness of the first Violent Femmes album.
posted by Seamus at 1:31 PM on November 19, 2009 [1 favorite]

Beck, Sea Change
Bon Iver, For Emma, Forever Ago
Frank Sinatra, In the Wee Small Hours
Otis Redding, Otis Blue
Ryan Adams, Heartbreaker
posted by Clambone at 1:31 PM on November 19, 2009

Oh yes, I forgot to mention Blood on the Tracks, which I own, and have also been listening to on repeat. Excellent suggestions!
posted by dhn at 1:31 PM on November 19, 2009

Cursive's Domestica
posted by NoRelationToLea at 1:32 PM on November 19, 2009 [1 favorite]

Kanye's "808's & Heartbreak" is all about his break-up with his fiance. I don't know how sympathetic of a figure Kanye is these days, but it's actually a pretty good album.
posted by eggplantplacebo at 1:33 PM on November 19, 2009 [2 favorites]

Nthing Sea Change. Man, that album got me through a tough one.
posted by Lutoslawski at 1:34 PM on November 19, 2009

PJ Harvey's Uh Huh Her was, for me, the ultimate breakup album. Every song on it tells you this is someone who's gotten her heart shattered, and she vacillates between venom-spitting rage and quiet sadness.
posted by katillathehun at 1:35 PM on November 19, 2009 [1 favorite]

I'm Alive by Jackson Browne. Pain, pain, pain, heartache and more pain.
posted by plinth at 1:37 PM on November 19, 2009

Ben Folds' Whatever and Ever Amen.
posted by ThePinkSuperhero at 1:37 PM on November 19, 2009 [1 favorite]

Man, clambone mentioned nearly everything I was gonna say (with special props to Beck, Otis Redding, and Sinatra)! I'd also add Springsteen's Tunnel of Love to the list.
posted by scody at 1:39 PM on November 19, 2009

rilo kiley - execution of all things
posted by nadawi at 1:39 PM on November 19, 2009

The Mountain Goats - Tallahassee

-An entire album about a married couple constantly on the edge of divorce.

posted by azarbayejani at 1:39 PM on November 19, 2009 [1 favorite]

Peter Gabriel's Us. He actually went through TWO breakups while producing it, ultimately also going through some kind of intense "what the hell AM I doing wrong when it comes to relationships here" therapy, and...you can tell.

And damn if it doesn't still sound awesome.
posted by EmpressCallipygos at 1:39 PM on November 19, 2009

Shoot Out the Lights - Richard and Linda Thompson
posted by octothorpe at 1:40 PM on November 19, 2009 [3 favorites]

John Mayer’s new album, Battle Studies, is a breakup album. Has some excellent tunes on it.
posted by yawper at 1:42 PM on November 19, 2009 [1 favorite]

Marvin Gaye, Here My Dear. It's even fairly infamous as a breakup album, with urban legends that it was recorded only because his ex-wife would get all of the proceeds. In actuality, it's not a contractual obligation album, but is a fairly heartfelt album about the dissolution of his marriage.
posted by UrineSoakedRube at 1:42 PM on November 19, 2009 [1 favorite]

Oh, and it may be a bit of a cliche, but don't forget Fleetwood Mac's Rumours -- it chronicles everyone in the band breaking up, basically, and it really is one hell of an album.
posted by scody at 1:43 PM on November 19, 2009 [4 favorites]

Elvis Costello - Imperial Bedroom!

Also, Garbage's first album - Garbage.

(Really tho, almost any Elvis Costello record pre-2000 is rife with "I love you/you suck!!" type songs. He's the master of that genre, in my humble opinion;)
posted by jbenben at 1:44 PM on November 19, 2009

Not to answer my own question (because, keep your answers coming!), but I also just remembered two of mine: Bitter by Me'shell Ndegeocello and Tracy Chapman's Telling Stories.
posted by dhn at 1:46 PM on November 19, 2009

Prolonging the Magic by Cake
posted by kathrineg at 1:46 PM on November 19, 2009

Tallahassee by the Mountain Goats is the 2nd best breakup album in English-language pop music so I'm v. glad that azabayejani mentioned it.

The best and I can't believe noone has said this is Rumours by Fleetwood Mac. What if you got a bunch of extremely talented songwriters and musicians to all break the fuck up with each other while producing an album about it? It's like a lab experiment comic book backstory. Other bands dream about writing the lousier tracks on this album. Never Going Back Again actually sounds like recovery, the monotonous cheer of the guitar, faking its way over Lindsay Buckhingham howling. Don't Stop sounds happy until you listen to it and get depressed and you figure out that it's like being a Beckett character who can only vomit into a sink and eat wonderbread but you're just all, "Yep, gotta keep vomiting, must keep eating wonderbread."

BONUS ROUND: my favourite nonenglish breakup song is Gute Nacht from Schubert's Winterreise, especially sung by Thomas Quasthoff.
posted by voronoi at 1:47 PM on November 19, 2009 [2 favorites]

"I need you, come back, fuck off, you suck."

Not an album, but as a song I think Ani DiFranco's Untouchable Face covers those four points pretty tidily.

(Or live, if you prefer.)
posted by rokusan at 1:50 PM on November 19, 2009

The Last 5 Years is what you'd get if you combined Memento with a failed marriage, and then made it into a musical. It's this weird progression that has you yo-yoing between first date bliss and post-breakup agony, but you have to like showtunes.
posted by Diagonalize at 1:50 PM on November 19, 2009

Definitely Rumours and Sea Change and I would throw Purple Rain and 69 Love Songs on top of that.
posted by milarepa at 1:50 PM on November 19, 2009 [1 favorite]

I believe Nine Inch Nails' Pretty Hate Machine is all about one girl.
posted by Cogito at 1:51 PM on November 19, 2009 [1 favorite]

The new Pete Yorn and Scarlett Johansson album, called Break Up, is essentially the tale of a relationship through a series of duets.
posted by cmgonzalez at 1:52 PM on November 19, 2009

ani difranco - dilate

so fuck you, and your untouchable face - and fuck you, for existing in the first place - who am i that i should be vying for your touch - who am i bet you can't even tell me that much

i used to be a superhero, no one could touch me not even myself, you are like a phone booth that i somehow stumbled into - and now look at me, i am just like everybody else

when i say you sucked my brain out the english translation is i am in love with you and it is no fun - but i don't use words like love 'cuz words like that don't matter - but don't look so offended you know, you should be flattered

like how could you do nothing and say, i'm doing my best - how could you take almost everything and then come back for the rest - how could you beg me to stay, reach out your hands and plead, and then pack up your eyes and run away as soon as i agreed


tonight you stooped to my level, i am your mangy little whore - now you're trying to find your underwear and then your socks and then the door - and you're trying to find a reason why you have to leave but i know it's 'cuz you think you're adam and you think i'm eve
posted by nadawi at 1:52 PM on November 19, 2009 [3 favorites]

I promise you, if you straight up blindly buy The Meadowlands by the Wrens for this purpose, you will not regret it one bit.
posted by sarahj at 1:53 PM on November 19, 2009 [3 favorites]

haha - yes, rokusan - but yeah, the whole dilate album is great.
posted by nadawi at 1:53 PM on November 19, 2009

Oh someone mentioned it, sorry. Don't I feel like a jerk.

One other good one that's only available on file sharing is the Mountain Goats' unreleased Hail and Farewell Gothenburg, which has unpolished first takes of half-written songs, full of agony and lines like "The way you disappeared gradually / made a very patient man of me."

Also I was just introduced to a musical called The Last Five Years by Jason Robert Brown, which is remarkable, it's a musical for two people, a man and a woman who sing about their marriage, one beginning from the beginning going forward, one starting from the end and going backwards. In the middle, they cross over and sing one song together. It is great. If musicals don't drive you insane, and even if they do, the album of this is an incredible breakup recording.
posted by voronoi at 1:54 PM on November 19, 2009

Songs of Leonard Cohen.
posted by something something at 1:57 PM on November 19, 2009

The Wedding Present - Bizarro

Eric's Trip - Love Tara / Julie Doiron - Broken Girl
posted by Sys Rq at 2:01 PM on November 19, 2009

Lee Hazlewood - Requiem for an Almost Lady
posted by hydrophonic at 2:02 PM on November 19, 2009

Dusty In Memphis.
posted by The Whelk at 2:03 PM on November 19, 2009 [1 favorite]

I'd recommend Gentlemen by the Afghan Whigs. Listening to Greg Dulli plumb the depths of his soul and all the ways he's fucked his lover over should make you feel better. At least I hope that it won't make you feel worse.
posted by friendlyjuan at 2:04 PM on November 19, 2009 [2 favorites]

Amy Winehouse's Back to Black.
posted by Unicorn on the cob at 2:07 PM on November 19, 2009

Nick Cave - The Boatman's Call

including such delights as People Ain't No Good:

To our love send a dozen white lilies
To our love send a coffin of wood
To our love let all the pink-eyed pigeons coo
That people they just ain't no good
To our love send back all the letters
To our love a valentine of blood
To our love let all the jilted lovers cry
That people they just ain't no good

It ain't that in their hearts they're bad
They can comfort you, some even try
They nurse you when you're ill of health
They bury you when you go and die
It ain't that in their hearts they're bad
They'd stick by you if they could
But that's just bullshit baby
People just ain't no good

Now that's some good wallowing.
posted by Kafkaesque at 2:08 PM on November 19, 2009 [1 favorite]

Joni Mitchell's Blue... I think it was directly inspired by her breakup with Graham Nash.

Also, even if the entirety of Jagged Little Pill isn't as angry as You Oughta Know, it's a pretty awesome breakup album.
posted by bookgirl18 at 2:08 PM on November 19, 2009

Control - Pedro the Lion.

Axxess & Ace - Songs: Ohia.
posted by shakespeherian at 2:09 PM on November 19, 2009

Elvis Costello - Blood & Chocolate.
posted by stennieville at 2:12 PM on November 19, 2009

The Microphones - The Glow p. 2
posted by one_bean at 2:19 PM on November 19, 2009

florence and the machine- lungs
howling bells- radio wars
lily allen- alright still
a fine frenzy- one cell in the sea
deathcab for cutie- transatlanticism
madeleine peyroux- bare bones
posted by raw sugar at 2:20 PM on November 19, 2009

I've been dealing with a breakup too, and I've found these three things that really helped me the most:

The Postal Service album
The Magnetic Fields '69 Love songs' album
MeFi Music! No seriously, there are a lot of tracks that you can throw together in a little playlist (a little self-made album if you will), that might be of use to you during this sucky time. Here are some of the tracks that have been on super-duper repeat to get me through:
Flyball's Lament – ORthey
Goodbye, dear heart – bicyclefish
Making Me Nervous – frenetic (aka, Brad Sucks)
Halleluyeah! – The World Famous
The Gilded Cage – saulgoodman (a little bit existential, and good for big picture perspective)
Don't fear the reaper (cover) – Kimyo
Requiem for the Living – goodnewsfortheinsane
Floating – csimpkins (this song was actually written for his unborn son, but I've been finding it to be an oddly beautiful and apt metaphor for a time like this)

Also, there's a boatload of great moody and/or upbeat instrumentals too. I've found that rifling through the random track popout player has been a wonderfully soothing timesuck.
posted by iamkimiam at 2:21 PM on November 19, 2009 [1 favorite]

Jagged Little Pill isn't completely about a breakup but has several related songs.
posted by Hardcore Poser at 2:23 PM on November 19, 2009

Seconding Shoot Out The Lights: although a lot of the songs were recorded before the split, it's hard not to read it as a breakup/breakdown album, especially in the context of the notorious US tour that they were obliged to do for the album.

Ladies and Gentlemen, We Are Floating In Space. (Which you can listen to, if you like, alongside The Verve's Urban Hymns, for the flip side.)
posted by holgate at 2:24 PM on November 19, 2009

See also any of Tindersticks' first four albums. Especially Curtains.
posted by Kafkaesque at 2:32 PM on November 19, 2009 [1 favorite]

Sugar, Copper Blue.
posted by kirkaracha at 2:33 PM on November 19, 2009 [1 favorite]

Forever Blue by Chris Isaak - written after he got his heart broken.

(I feel like this may not be a 'cool' album and I'm outing myself as totally uncool. Like high school all over again)
posted by hydrobatidae at 2:36 PM on November 19, 2009

I'm also a recent member of the broken hearted club. I've been wallowing along with:

- Multiple songs by The Mountain Goats, particularly all of Tallahassee as well as Get Lonely (skip straight to Woke Up New if you want a pure injection of perfectly-written misery into your arm.)

- My favourite break-up album of all time is Ladies and Gentlemen We Are Floating In Space by Spiritualized. For the full effect you need to lie on the floor and turn out the lights and listen to it the whole way through. For the redux, skip to 'Broken Heart' and play on repeat, possibly while stabbing yourself repeatedly in the tender part of the brain with some safety scissors. I'm now in the weird position where I've listened to this album so many times at rough points in my life it reminds me less of the misery I'm in now and more of all the cumulative miseries that have gone before, and how I got over them. It's immensely comforting. It reminds me that I was letting Jason Spaceman wail me to sleep before I ever met my last partner and will do long after I lose the next.
posted by somergames at 2:37 PM on November 19, 2009

Try Joni Mitchell's Both Sides Now album.

It's "a programmatic suite documenting a relationship from initial flirtation through optimistic consummation, metamorphosing into disillusionment, ironic despair, and finally resolving in the philosophical overview of acceptance and the probability of the cycle repeating itself".

Damn fine breakup music, with an eye towards you'll-get-over-it.

Also, Late For The Sky by Jackson Brown.
posted by MrVisible at 2:38 PM on November 19, 2009

Tallahassee by The Mountain Goats!
posted by OmieWise at 2:45 PM on November 19, 2009

Insignificance by Jim O'Rourke. It's absolutely vicious, but in a sort of abstract and dreamy way. It took me several listens before I realized just how angry it was. Also, the singing and musicianship is top rate.
posted by elder18 at 2:46 PM on November 19, 2009

Jane Doe by Converge. It's definitely... cathartic.
posted by The Michael The at 2:46 PM on November 19, 2009 [1 favorite]

Richard Buckner, "Devotion + Doubt" - even the songs that aren't about anything.
posted by notsnot at 2:54 PM on November 19, 2009

Fiona Apple, When the Pawn...

From the very first track to the last line of the very last, this album really sums up that feeling of being poisoned with love for someone you either can't have or don't really want.
posted by hermitosis at 2:55 PM on November 19, 2009

Melissa Etheridge's entire first album is full of break-up music.
posted by rmd1023 at 2:57 PM on November 19, 2009

Yes, Jagged Little Pill is a good one. You can also listen to it and be glad that no matter what else has happened, at least you've never dated Dave Coulier (I hope).

Pet Sounds isn't technically a break-up album, but a lot of the songs are about difficulties in love, and it's really just great anytime.
Along the same lines, Abbey Road has a break-uppy feel and some of the songs are especially powerful.
Mutations by Beck is not as outright about a break-up as Sea Change, but it definitely has several songs that seem to be about a breakup (especially Nobody's Fault But My Own).
The Colour and the Shape by the Foo Fighters
Forever Changes by Love really seems like a break-up album to me
Can't Buy a Thrill-Steely Dan. "Dirty Work," "Midnight Cruiser," and a few others are especially good
posted by ishotjr at 2:59 PM on November 19, 2009

Highlighting The Magnetic Fields 69 Love Songs. Love from every angle, especially the bitter post love one.

Just got second row tickets to their February show in Toronto. Squeeeeeeee...
posted by yellowbinder at 3:05 PM on November 19, 2009 [3 favorites]

Seconding Blue by Joni Mitchell.
posted by granted at 3:05 PM on November 19, 2009

sarahj is absolutely 100% right about The Meadowlands. Can't Nth that enough times.

Also, William Fitzsimmons' The Sparrow and the Crow, Now It's Overhead's self-titled, and The Jealous Sound's Kill Them With Kindness.
posted by axiom at 3:07 PM on November 19, 2009

technically you could buy the CD of the show... so I'm hoping this counts as an album ;)

This American Life - "Break-Up"
posted by muscat at 3:13 PM on November 19, 2009

Highlighting The Magnetic Fields 69 Love Songs.

highlighted again. It's retty much Breakup Music Engine.

Also the Dresden Doll's first album. "Glass Slipper" and "Missed Me: still give me shivers.
posted by The Whelk at 3:24 PM on November 19, 2009 [1 favorite]

sarahj and axiom got there first, but I completely agree that The Meadowlands by the Wrens is what you want.
posted by kms at 3:49 PM on November 19, 2009

nthing 69 Love Songs. There's enough on that album to take you through any stage of a relationship.
posted by ripley_ at 3:55 PM on November 19, 2009

Superchunk, Foolish. That's some painful breakings-up, that is.
posted by Coatlicue at 4:22 PM on November 19, 2009 [1 favorite]

Fiona Apple - When the Pawn
Magnetic Fields - 69 Love Songs
LCD Soundsystem - Sound of Silver
Camera Obscura - My Maudlin Career

60's girl groups like The Ronettes, The Essex, and The Shangri-Las.
posted by blackcatcuriouser at 4:43 PM on November 19, 2009 [1 favorite]

Marvin Gaye's Here, My Dear.
posted by fuse theorem at 4:50 PM on November 19, 2009 [1 favorite]

Sade's Promise, in particular, "You're Not the Man." cut.
posted by jadepearl at 4:56 PM on November 19, 2009

Matthew Sweet - Altered Beast.
posted by any major dude at 4:56 PM on November 19, 2009

that dog - retreat from the sun
posted by kid_dynamite at 4:57 PM on November 19, 2009

I'm jumping in on the Mountain Goats bandwagon. Get Lonely is actually a breakup album; it's sort of the story arch of a pretty nasty breakup (complete with a bit of optimism about the future).
posted by NoraReed at 4:58 PM on November 19, 2009

Urge Overkill's album Exit The Dragon
Tool's album Opiate (particularly the track "Cold and Ugly")
posted by The World Famous at 5:01 PM on November 19, 2009

Nthing Here, My Dear. I think it's the best album Marvin Gaye ever recorded.
posted by box at 5:13 PM on November 19, 2009

I See A Darkness by Bonnie Prince Billy (Will Oldham)
posted by msalt at 5:22 PM on November 19, 2009

of Montreal's The Bedside Drama: A Petite Tragedy. So cute. So familiar. So sad.
posted by synthedelic at 5:52 PM on November 19, 2009

Marvin Gaye's Here, My Dear.


Incredible record, incredible back-story, incredible album art. And my pick of the entire Gaye catalog.
posted by Joseph Gurl at 5:54 PM on November 19, 2009

Portishead's Portishead is dark and noirish with portents of doomed romance throughout. Humming is my fave track but the whole thing is great and I'm currently listening to it 3 times a week.
posted by Scoo at 6:25 PM on November 19, 2009

Sorry, just went through my itunes to help me think straight:

Jawbreaker- Dear you
Almost anything by Bright eyes
Descendents- many great songs, hard to choose one album, but I'd say 2 things at once would be the best
the good life- black out
gunmoll- anger management in 4 chords
jets to brazil- 4 cornered night- very emotional, not so much about breaking up
lucero-that much further west
pixies- doolittle
wilco- yankee hotel foxtrot
posted by TheBones at 7:01 PM on November 19, 2009 [1 favorite]

"Workers Playtime" by Billy Bragg. My heart was broken and I played it and played it. These songs in particular, "Must I Paint You a Picture?", "Valentine's Day is Over" (that's a cover, I couldn't find a clip of Billy singing that one), "The Only One" and "The Short Answer" really kill me.
posted by h00py at 7:31 PM on November 19, 2009

Smog The Doctor Came at Dawn
It's awfully creepy and grim, tbh.

I guess after Nick and Peej broke up -
Nick Cave The Boatman's Call, PJ Harvey Is This Desire?
posted by citron at 7:42 PM on November 19, 2009 [2 favorites]

Paraphrase (I think Rick Johnson from Creem):

"Whenever I was the on the phone talking with someone I had broken up with a few weeks ago, I would always hear Joni Mitchell's 'Blue' playing in the background."
posted by ovvl at 8:05 PM on November 19, 2009

No one has mentioned The Cure, Disintegration?

Pictures Of You

I've been looking so long at my pictures of
you that I almost believe that they're real
I've been living so long with my pictures of you that
I almost believe that the pictures are all I can
feel

Remembering you standing quiet in the rain as
I ran to your heart to be near
And we kissed as the sky fell in holding you close how I always held close in your fear
Remembering you running soft through the night
You were bigger and brighter and whiter than snow
Screamed at the make-believe screamed at the sky
And you finally found all your courage to let it all go

Remembering you fallen into my arms
Crying for the death of your heart
You were stone white so delicate
So lost in the cold
You were always so lost in the dark remembering you
How you used to be so drowned you were
Angels so much more than everything
oh hold for the last time then slip away quietly
Open my eyes but i never see anything

If only I had thought of the right words I could
have held on to your heart
If only I'd thought of the right words I wouldn't be breaking apart all my pictures of you

Looking so long at these pictures of you but I
never hold on to your heart
Looking so long for the words to be true but always just breaking apart my pictures of you

There was nothing in the world that I ever
wanted more
Than to feel you deep in my heart
There was nothing in the world that I ever
wanted more
Than to never feel the breaking apart
My pictures of you
posted by fieldtrip at 8:18 PM on November 19, 2009 [1 favorite]

If you're going to use The Cure as breakup music, go all the way and listen to the Faith and Pornography albums. Disintegration is for lightweight breakups.
posted by The World Famous at 8:29 PM on November 19, 2009

Smashing Pumpkins, Adore
posted by EmilyClimbs at 8:30 PM on November 19, 2009

Aimee Mann - I'm with Stupid
posted by zix at 8:43 PM on November 19, 2009

Ugh, I'm in the same boat.

I nominate:

Cure For Pain by Morphine: the obvious breakup song on here would be "I'm Free Now" but the entire album is good.

Songs of Love and Hate by Leonard Cohen: be careful about listening to "Dress Rehearsal Rag" as it's really depressing. Definitely listen to "Avalanche" - it is an amazing song and one of my favorites by Cohen. Famous Blue Raincoat is well known, a letter written by Cohen to his wife's lover, perhaps. Joan of Arc, the last song, is stunning. It ends with some of my favorite lyrics, ever written:

Myself I long for love and light,
But must it come so cruel, and oh so bright?

Everything Sucks and I Don't Want to Grow Up by The Descendents. Of these, I recommend: My World, Can't Go Back, Christmas Vacation, Rotting Out, and Sick-O-Me.
posted by jacquilinala at 8:44 PM on November 19, 2009

Seconding Sugar's Copper Blue.
posted by SisterHavana at 9:08 PM on November 19, 2009

Local H - Twelve Angry Months
posted by sinfony at 9:08 PM on November 19, 2009

The Smiths, The Smiths (actually, any Smiths album!)
Morrissey, Viva Hate
posted by SisterHavana at 9:12 PM on November 19, 2009

Wow, the bases have been covered, so consider any repeat mentions an endorsement of the previous Mefite's impeccable taste, I can only add more also-rans.
Photographs Of Feeling Bob Lind. Tan! Certainly, Sir. Bring On The Snakes Crooked Fingers. Rumours Fleetwood Mac. No One Cares Frank Sinatra. Alone Again (Naturally) Gilbert O'Sullivan. Is A Woman Lambchop. Requiem For An Almost Lady Lee Hazlewood. Doctor Came At Dawn (Smog). Get Lost Magnetic Fields. Tallahassee Mountain Goats. Albums by East River Pipe and Scott Walker, as well as Low by David Bowie seem appropriate, but only when breaking up with concepts can be just as cathartic as breaking up with people. I suppose any album can serve as a penultimate break-up album in the right context. Kind of like how a couple's favorite song can forever taint an album.
posted by ktrey at 9:13 PM on November 19, 2009

nthing Meadowlands and Dilate. Also, Boys for Pele by Tori Amos and and Firewater's The Golden Hour.
posted by EvaDestruction at 9:19 PM on November 19, 2009

Neil Young - On The Beach
Certain tracks, like "Motion Pictures (For Carrie)" were written when Neil could sense that Carrie Snodgress was cheating on him. Perhaps the best, saddest LP of all time. You'll want to invite the sad, emotionally shattered Neil into your house and feed him a hot meal and give him a hug.

Beck - Sea Change
Borrowing liberally from the arrangements of Serge Gainsbourg and Scott Walker, this is far and away the best thing he's ever done.

Scott Walker - Scott 1-4; Til the Band Comes In
All of the music on these records is worth your time. Particularly, tracks like "My Death," "The Big Hurt" (both from Scott 1, "The World's Strongest Man" and "Time Operator" (from Til the Band Comes In) are exactly what you're looking for.
posted by porn in the woods at 9:37 PM on November 19, 2009

I've said it before and I'll say it again: Sleater Kinney "Dig Me Out" and Veruca Saly "resolver".

Particularly the latter -- try dealing with a band break-up AND a relationship break-up... And your beau's new lady being Winona Ryder. OWww!

Both are great, cathartic albums.
posted by indienial at 1:13 AM on November 20, 2009

Son of an evil reindeer by The Reindeer Section. Not officially a break-up album but many of the songs chart the rise and fall of relationship angst. It's a beautiful album and perfect for a good wallow.
posted by freya_lamb at 3:02 AM on November 20, 2009

One record that's helped get me through the last year or so is Willie Nelson's Red Headed Stranger.

Now, I know Willie's not for everyone, but...boy that record can make you almost GLAD to "wild in your sorrow, ridin' and hidin' your pain" which...can be a nice break from NOT doing that. Plus, "Can I Sleep In Your Arms Tonight" is one of the saddest, most beautiful songs in the history of the world.

Ok, there might be some hyperbole there, but I like the record. It's given me a nice balance between wallowing and life-affirming feelings.
posted by Richat at 4:47 AM on November 20, 2009 [1 favorite]

Any album by Everything but the Girl probably works as a break up album. Literally. Walking Wounded in particular seems like a straight up break up album. There are so many depressing as fuck songs on that album. It opens with Before Today, and features Single which is depressing as fuck, and Walking Wounded.
posted by chunking express at 10:57 AM on November 20, 2009

Actually, Amplified Heart by EBTG would probably be a good listen too. Roller Coaster is an awesome song. It opens with: "I still haven't got over it even now. I want to spend huge amounts of time on my own." And it only gets better.
posted by chunking express at 11:01 AM on November 20, 2009

Seconding Disintegration. Lightweight my ass! :)
posted by Citrus at 11:22 AM on November 20, 2009

Roy Orbison didn't sing about happy things. Crying, It's Over, Only the Lonely.
posted by talldean at 6:31 PM on November 20, 2009

Elephants... Teeth Sinking Into Heart by Rachael Yamagata. It's a two part CD- the first disc is all about the sadness that comes along with a breakup, and then on the second, she gets pissed.
posted by mollywas at 7:28 PM on November 21, 2009