I recently decided to ask all of my colleagues at Discogs which album they considered the saddest of all-time. We had tapped into the deep music knowledge of Discogs staff in that past for the best music for a BBQ and the best Halloween records, so why not explore sad records too? What surprised and intrigued me was the massive amount of replies and comments we received on the Blog and social media accounts after publishing the article and sharing it with the Discogs Community. By pure chance, I clicked the right button: Everybody loves sad music. I’m confident that the opposite subject, covering happy music, wouldn’t be as relatable and popular. It’s taken me forever but it’s finally happening, I’m sitting down in front of my computer deciding how to speak about sad music and albums that you, our beloved community, have mentioned.

The main disagreement with our previous blog post was that we “forgot” about a lot of the saddest albums in history. In defense of the Discogs staff, there are only so many of us. The rules for our Staff Picks are clear: one release per person. Trust me on this one, it would be much easier for each of us to pick 50 than just one. The rules that apply are similar to those at your nearest casino roulette table: If you bet all of your money on just one number, the odds are incredibly high that you won’t win anything. So this time, without those limitations, I’ll cover much more sad music, spanning a diverse set of genres, artists and moods.

Before I jump into the usual list format, I wanted to reflect on why sad music has such an impact on listeners’ lives. I easily found two great pieces in Psychology Today. The first one, written by Dr. Robert Berezin, is called . As straightforward as it sounds, Dr. Berezin explored the different reasons why sad music is a great companion under many different life circumstances. The second one, written by Ph.D. Shahram Heshmat, is called and it points out reasons that you might have never thought about before, such as the production of prolactin or the role of empathy. I recommend you read both since I admit my inability to put into words so precisely the reasons why we, as humans, use sad music as such an endless resource.

Now that the doctors have covered the psychological reasons why we turn to sad music under so many different circumstances, it’s my time to do what we do best at Discogs, cover the music side of things. I wanted to send a heartful “thank you” to my colleague Jess Thompson for the beautiful texts she’s written to accompany Sea Change, Either/Or, Pink Moon, White Chalk, Dummy, Purple Mountains, and Carrie & Lowell.

35 Albums That Will Hit You Right In The Feels

Beck – Sea Change (2002)

When news broke earlier this year that divorce was on the cards for Beck and his wife of almost 15 years, a small, petty part of me that Only Cares About The Music™ (whatever, you have that part too) was stoked. Another Beck breakup record was sure to follow! Sad-Beck might be Beck at his finest.

If you’re looking for proof of that, look no further than Sea Change. It’s an unrivaled masterpiece of a breakup album. Where its predecessor, was all “Peaches & Cream” and “Nicotine & Gravy,”” Sea Change was “Lonesome Tears” and “Lost Causes.” Heartbreak radiates from this record and his breakup with a longtime girlfriend was the major influence for the dramatic shift in tone. You’d be upset too; a few weeks before his 30th birthday he learned of his fiance’s affair with a member of Whiskey Biscuit.

Sea Change provides plenty of opportunity to wallow, but as a whole it’s also strangely uplifting. You also get the sense that he’s going to come out of the other side of this record exorcised and ultimately all right. What Beck delivers with Sea Change is catharsis. Through his despair into this album, he’s also provided an outlet for anyone who has felt similarly lousy at the end of a relationship. BYOTears.

Saddest moment

It’s only lies that i’m living,
It’s only tears that I’m crying,
It’s only you I’m losing,
Guess I’m doing fine

Big Star – 3rd / Sister Lovers (1975)

Part of what makes the third and last album by Big Star such a heartbreaking one comes with knowing the details of its recording and release. After not succeeding commercially with and , 3rd / Sister Lovers was recorded in 1975 and then slated by the company until it was finally released in 1978. By that time, Big Star was no more and, to add insult to the already ill-starred career of the band, their third album was met with apathy by both audience and critics back in the day. If you’ve ever listened to this record, even just once, you’ll understand how unfair this is. 3rd is an aching, extremely beautiful collection of songs. It’s not all gloomy, the beginning of “Kizza Me” gives a hint of cheerful power-pop glory before the album sinks into some of the most depressing lyrics and sounds ever produced in the seventies.

Saddest moment

It’s hard not to weep when Alex Chilton sings these lines in the devastating, “Holocaust”:

Your mother’s dead, you’re on your own
She’s in her bed

Bon Iver – For Emma, Forever Ago (2008)

In 2008, it was hard to foresee the huge success that Bon Iver had with this intimate, small miracle of a record. But sometimes, luckily, the music that connects with the masses can be this gorgeous. For Emma, Forever Ago has been labeled by many as THE breakup album. And while it’s not the only one out there on the subject, it might be indeed the most popular of them all. Justin Vernon recorded it in a cabin between 2006 and 2007 starting, if you ask me, a weird trend for many other musicians to do exactly the same with – obviously – unequal results. Few albums out there feel as healing and empathetic as this one when you’re going through a breakup.

Saddest moment

In an album full of those moments, it’s safe to say that “Skinny Love” hits all the right buttons.

Bonnie “Prince” Billy – I See A Darkness (1999)

I remember listening to this album obsessively in the early 2000s. Just to give you an insight into how heavy I See A Darkness feels, I didn’t speak English – or at least decent English – at the time and I could still perceive the great sadness that flows through it. It’s a magical record. To me and to many others, the highest peak of a career filled with incredible music. Bonnie “Prince” Billy’s honesty and lyrical quality can be felt in every corner of this masterpiece. And just in case you didn’t get it from the artwork: Yes, this is an album about death. And about many more things. Please, listen to it right now if you haven’t before.

Saddest moment

“I See A Darkness,” the song, is not only one of the saddest songs of all-time, but also one of the most beautiful and fragile ones.

Cat Power – Moon Pix (1998)

How much devastation are you able to stand? This question is an important one to ask before playing Moon Pix for someone. For many, the best collection of songs by Chan Marshall, and that’s a lot taking into account the unparalleled brilliance of the singer-songwriter’s career. Written in full after a hallucinatory nightmare, Moon Pix showed Cat Power at her most vulnerable yet, and on the way delivered some of the most achingly beautiful songs ever written. But be prepared because nobody crosses through Moon Pix unharmed.

Saddest moment

To many, the saddest story told in the album is “Cross Bones Style.” Rightfully so. These verses on “He Turns Down,” a song about being rejected by God, have always stuck with me:

It’s not me, I am pretending
I’m not saved,
he turned me down.
He turns down

Codeine – Frigid Stars LP (1990)

Sometimes I feel like Codeine will never get as much appreciation as they deserve. The pioneers of slowcore released this incredible album in 1990 and cleared the path for many bands to follow. Not many understood that rock music could be this slow and this powerful at the same time. Emo much before emo existed. Raw, emotional, and evocative. Frigid Stars LP still remains as one of the best albums of the genre and it will keep bringing us down for many decades to come.

Saddest moment

For an album with the emotional depth of Frigid Stars LP, it’s impossible to pick just one moment.

David Bowie – ★ (Blackstar) (2016)

Everything around the last record of David Bowie is designed to make you feel like you’ve been run over by a truck. Released days before the death of David Bowie, ★ (Blackstar) immediately took on a new and deeper significance. It’s the final statement of one of the most important artists in history. 7 songs clocking in at 41 minutes were enough for this album to become one of the most important in a triumphant career and also the second most collected album of the decade by the Discogs Community. If this was goodbye, what a way to say it.

Saddest moment

The first lines of “Lazarus” always hit like a punch in the gut of the stomach:

Look up here, I’m in heaven
I’ve got scars that can’t be seen
I’ve got drama, can’t be stolen
Everybody knows me now

Elliott Smith – Either/Or (1997)

Sad and Elliott Smith are two inextricable companions. Picking the saddest of his albums is a futile exercise, but here we are.

Where some of his later albums, and leaned further into electric guitar and piano arrangements – even flirting with orchestras on Figure 8 – Either/Or is primarily Smith with an acoustic guitar and fragile, whispery vocals. Either/Or runs us through a spectrum of emotion, pushing off slowly with “Speed Trials,” raging against “Pictures Of Me,” plunging into full-scale despair on “No Name No. 5” and tentatively reemerging on “Cupid’s Trick.”

For such a despairing album, Elliott leaves us on a bright note of hope with “Say Yes,” albeit typically Smith-style muted hope. Don’t take it personally, that current of sadness is never too far from the surface.

Saddest moment

No contest – the whole of “No Name No. 5”, but especially:

Got a broken heart and your name on my cast, and everybody’s gone at last

Grandaddy – The Sophtware Slump (2000)

Few albums, if any, captured the technologic disappointment awaiting us with the energy of the sophomore album by Grandaddy. The Sophtware Slump was released soon after the turn of the millennium and it combined traditional elements of the American underground with unexpected themes for the time. This is not science fiction, this is an utterly sensitive author opening up in infinite new creative ways and letting us have a look at his anxiety. Jason Lytle was quoted at the time saying, “…I just remember everything out there was dusty. Humidity and dust,” and that he made the recordings “…in my boxer shorts, bent over keyboards with sweat dripping off my forehead, frustrated, hungover and trying to call my coke dealer.”

Saddest moment

“Jed The Humanoid” is a huge tearjerker.

Grouper – Ruins (2014)

I was about to write in here: everything ever released by Grouper. Liz Harris has built one of the most wonderfully unique careers in the industry since she started releasing music in the mid-2000s. Her music exists outside of time and trends, and what you feel the first time you listen to it is very similar to finding hidden treasure from a past civilization buried in the soil.

Mysterious, atmospheric, and haunting, Ruins was released in 2014. Because of how stripped down her songs are after years of heavy layering, it felt like her most direct and impactful release. Liz Harris, her piano, a portable 4-track recorder and a Sony stereo microphone were enough for her to capture the enigmatic and gloomy atmosphere that persists through the album.

I remember reading an interview back in the day in which she mentioned that this album represented “living in the remains of love.” It feels that profound.

Saddest moment

It’s impossible to choose, this whole album carries such a nostalgic and regretful mood.

Interpol – Turn On The Bright Lights (2002)

The debut album by Interpol is a whole mood in itself. Recorded only two months after 9/11 and released in August 2002, the record connected with a whole generation in a moment of collective existential dread. The line between oppressive and sad isn’t always clear, and that’s where Interpol found their voice in the new generation of rock bands at the turn of the millennium. To most fans, Turn On The Bright Lights remains their best effort almost 18 years after.

Saddest moment

This might be a very personal pick, but the whole melodic mood of the opener “Untitled” and those last two lines are devastating.

James Blake – James Blake (2011)

James Blake took the world by storm with this debut album. Not that we weren’t unaware of the immense talent of the British artist, all of his previous EPs were incredible. A new way of making music showcased his sensibilities to the world and the album was an instant hit. It wasn’t as easy as it looks like, his self-titled debut is still a demanding listen. Not only sonically, but the lyrics also dig deep into the soul of a tortured crooner. In his most recent release, Assume Form, James Blake deals with very different feelings, a much happier and fulfilled Blake is in front of our eyes. He made it.

Saddest moment

His rendition of Feist’s “Limit To Your Love” is simply perfect.

Joy Division – Unknown Pleasures (1979)

In our previous blog post, we got roasted pretty hard for not including one single album by Joy Division. I agree, probably no other band will ever achieve this level of sadness and depression while at the same time delivering good (even catchy) melodies and profound lyrics. At 40, Unknown Pleasures is still one of those albums that you come back to over and over each year, and few albums can stand the test of time with such grace.

Saddest moment

The whole album.

Leonard Cohen – Songs Of Love And Hate (1970)

Few albums out there evoke winter both in a metaphorical and literal way as Songs Of Love And Hate does. That’s not everything this record does right, it’s hard not to fall in love with its melancholic quality and with how Leonard Cohen even puts himself in the skin of Joan of Arc. Most of the time, when you think of sad albums, you think of minimal instrumentation and naked songwriting. That’s not what you’ll find here, Song Of Love And Hate is complex, lush, poetic and full of evocative images.

Saddest moment

It’s close to impossible to set the tone of a whole album the way “Avalanche” does.

Lisa Germano – Geek The Girl (1994)

Let me start out by thanking the Discogs Community for pointing me to this album. I was familiar with Lisa Germano probably thanks to the fact that she was part of the roster of 4AD during the nineties. But I never listened to any of her albums, and Geek The Girl feels like a revelation. While not necessarily sad at all times, whenever Lisa Germano tried to get there, she delivered stunning results. I can’t wait to listen to the rest of her discography.

Saddest moment

The beautiful instrumentation of “Cry Wolf” right before the horror of “… A Psychopath” (a song that even she had trouble recording due to the nature of the real 911 call used in the background)

Lou Reed – Berlin (1973)

A lot of our users were quick to claim that Berlin is the saddest album ever recorded. Lou Reed released Berlin in 1973 as a rock opera recalling the story of a couple – Jim and Caroline – whose lives spiral out of control while covering subjects as rough as drug addiction, prostitution, depression, domestic violence, and suicide. While each and every song doesn’t feel so heavy, certain parts of the album still feel dreadful.

Saddest moment

All the B-side of this album, when things get really ugly for the couple, is super sad. This includes kids crying in “The Kids.”

Low – I Could Live In Hope (1993)

In our Staff Picks post, I used my pick to choose as my number one saddest record of all time. I didn’t know we had so many Low fans in our audience, and many of you pointed out how you actually preferred their debut record, I Could Live In Hope. I’m not here to establish a weird self-competition on which album is sadder (or better for that matter.) In my book, both are fantastic examples of the endless talent of Alan Sparhawk and Mimi Parker, one of the most beloved and iconic couples of the American underground. I Could Live In Hope is still revered as the most representative slowcore album and one that opened infinite doors to other musicians by slowing down the rhythm.

And now that we’re here… this album also deserves a proper reissue.

Saddest moment

All of you probably have your own, it’s an album worth listening in its entirety every single time.

Mount Eerie – A Crow Looked At Me (2017)

No list about sad albums can do without A Crow Looked At Me. None. But this time, happily, we already included it in our previous list. For those unfamiliar with the story behind this album, Phil Elverum’s wife, Geneviève, died in 2015 four months after the birth of their first child of pancreatic cancer. I don’t know if you already feel like crying, but I do. As devastating as this all sounds, Mount Eerie took all of that sadness, grief, hopelessness, and disorientation and turned it into A Crow Looked At Me. A collection of songs so raw, so authentic, so deeply personal that it’s impossible to escape its sadness and, in a way, making it ours as well. Because empathy is one of the reasons why we all love sad music, A Crow Looked At Me is an album that relentlessly asks us to join Elverum through the dark path of grief.

Saddest moment

It’s literally impossible to choose one, but if these lines out of “Real Death” don’t make you weep, you have a problem:

A week after you died, a package with your name on it came, and
inside was a gift for our daughter you had ordered in secret, and
collapsed there on the front steps. I wailed.
A backpack for when she goes to school a couple years from now.

Nick Cave & The Bad Seeds – Ghosteen (2019)

Nobody can be emotionally prepared for this album. After the incredibly sad and unforgettable , Nick Cave continues mourning and takes us along with him. Even though officially it is not just about the tragedy, at times this album requires an insane amount of emotional stamina to stand. This double album is as beautiful as it gets, but be ready to get a lump in your throat throughout.

Saddest moment

I haven’t wrapped my head around it yet, I recommend you to listen to this album now and decide by yourself.

Nick Drake – Pink Moon (1972)

Although Nick Drake’s catalog is often associated with his struggle with depression, Cally Calloman of Bryter Music states that Drake was incapable of writing or and recording during periods of depression.

The music Drake manages to create with just his voice and an acoustic guitar is a testament to both his immense skill as a songwriter and guitar player. While Pink Moon will never be considered an upbeat album, it’s not especially dismal or bleak, and it’s not going to plunge you into depression.

Saddest moment

It’s hard not to be moved when he sings in “Place To Be”:

Now I’m darker than the deepest sea
Just hand me down, give me a place to be

Nico – Desertshore (1970)

Desertshore is such a raw, at times desperate, piece of music history. For Nico, the easiest would have been to simply remain as an appendix to The Velvet Underground history. But she was much more than that and she was ready to prove it to the world. After releasing the equally stunning and , Desertshore felt like her true leap of faith into unknown territory.

Desertshore is so passionate and so magnetic that once you’ve started playing it, there’s no way back. She dedicated “Janitor Of Lunacy” to her recently deceased friend Brian Jones, sang with her little child Ari in “Le Petit Chevalier” and collaborated with her then-boyfriend Philippe Garrel in the experimental film La Cicatrice Interieur (featuring music from the album as its soundtrack).

A legendary album by an artist who proved to be much more than a femme fatale. Also, how many other artists out there got their albums reworked by Throbbing Gristle?

Saddest moment

This album absolutely always brings me down when Nico sings achingly in “Afraid”:

You are beautiful and you are alone
You are beautiful and you are alone

PJ Harvey – White Chalk (2007)

The album is so affecting I can only listen to it when I’m in the most stable genius of moods. It’s a sharp departure from its predecessor, (and every other album she’s ever released), trading guitar and full band for an eerily stripped back piano and austere arrangements. Harvey also tries out a different vocal style for this album, moving into the higher end of her range, allowing her voice to take on more vulnerability, fragility, and precariousness at the edge of her register.

Where some of the albums on this list offer a contrast of upbeat instrumentals with despairing vocals, or glimpses of light at the corners of depression, White Chalk is unyieldingly grim. Sometimes you just want to revel in your sadness, and it’s comforting to have Harvey’s hand to hold to edge further into those depths.

Saddest moment

There’s a plethora to choose from here, but here’s one to launch your ship across those dark seas:

Please, don’t reproach me for just how empty my life has become 

Portishead – Dummy (1994)

Portishead’s genre-bending, widely revered debut album is often attributed with taking trip-hop mainstream. Even 25 years after it was released, nothing really sounds like Dummy. It gets under your skin and feels like being deserted on an alien planet. It’s lonely, but at the same time there’s so much to keep you occupied that you barely really notice. The effortless blend of hip-hop, soul, jazz and blues, topped with Beth Gibbons’ dazzlingly chilling vocals, it all works together so well.

Despite being a critical darling, the sad core of this album really creeps up on you. Pitchfork pointed out the irony of the title – more commonly referred to in the US as a pacifier – going on to describe the album is “discomfort food: curl-up-and-die music, head-under-the-covers music”.

Saddest moment

“Roads” is a strong contender for the most heartbreaking song of all-time, and also one which will bring you down each time.

Purple Mountains – Purple Mountains (2019)

After a long absence from music, fans rejoiced the welcome return of Silver Jews’ David Berman to the music scene under the moniker, Purple Mountains. It was his first studio album since SJ disbanded in 2009. While the self-titled debut is a stunning album in its own right, sadly, it’s become one of those albums whose listenings has been irrevocably colored by following tragedy after Berman took his life less than a month after the album was released. Although Berman had long struggled with treatment-resistant depression – compounded with the death of his mother and separation from his wife of 20 years – the completion of Purple Mountains seemed to buoy his spirits.

Musically, Purple Mountains is pretty upbeat and lively for a ‘sad’ record. I defy you not to dance around your living room to a song like “Margaritas at the Mall.” It’s like plastering a happy face shattered soul to face the world. Lyrically, poignant and bleak but with still brimming with Berman’s characteristic wit and uncompromising sense of humor.

It’s a beautiful, if painful, parting message from a man who was trying but couldn’t bear the weight of the world anymore.

Saddest moment

Starts at 0:01 and relents at the end.

Red House Painters – Down Colorful Hill (1992)

Here we go again. Officially nobody was happy to see that none of the Discogs staff picked a record by Red House Painters for the saddest album of all-time. Well, again my friends, you were very right. Down Colorful Hill is and will forever be in my top five, at least.

Red House Painters, the band fronted by Mark Kozelek (aka Sun Kil Moon) released their debut record in 1992 and it doesn’t get much more depressing than this when you’re 24. Only six songs and 43 minutes were enough for Red House Painters to establish themselves as one of the most revered bands of the nineties. Very few times the artwork of an album matched so perfectly the mood of its music. Don’t stop here, we have to thank Mark Kozelek for a whole career of heartbreaking music. So no, we haven’t forgotten about .

Saddest moment

I don’t know exactly why, but the opener “24” absolutely always gets me.

Radiohead – A Moon Shaped Pool (2016)

Don’t take me wrong, it’s not like we wouldn’t expect a certain dose of sadness in a Radiohead record. But A Moon Shaped Pool definitely caught many of us off-guard after . A Moon Shaped Pool explored thoroughly the dark corners of the soul, and it did it in such an orchestral and spectral way that at times it makes it hard to cope with it. It’s not an album I want to listen to when I’m feeling down, and you probably shouldn’t either.

Saddest moment

“Daydreaming” is the saddest Radiohead song ever, an absolutely devastating post-breakup statatement.

Smog – The Doctor Came At Dawn (1996)

With a career spanning three decades, Bill Callahan (fka Smog) is one of the greatest American singer-songwriters. The Doctor Came At Dawn is Smog at his most slowcore. Looking back, 1996 was a great year for this. And yet again, with such beautiful music coating it, the lyrics of the songs remain the true star of this release.

Saddest moment

Even though “Hangman Blues” is the most devastating song in its simplicity, I think the post-breakup heartache depicted in “All Your Women Things” is the song that really brings me down.

Songs: Ohia – Ghost Tropic (2000)

I just can’t put it better to words than my colleague Jason did in our previous blog post, so here you go:
Lumbering and somber, but somehow effortlessly incorporates tropical birdsong. The lyrics are bleak, even for Jason Molina, and they hang suspended for perusal. A harrowing, gorgeous meditation on an ending.
I asked him to pick as well his saddest moment of the record:

Saddest moment

I picked Ghost Tropic over other Molina records with bleaker lyrics mostly because of “Not Just a Ghost’s Heart.” The record feels like a single unbroken mood, for which that song is a microcosm. It’s a giant messy dirge that invites wallowing; in fits of melancholy I have listened to that song repeatedly for days.

Sparklehorse – It’s A Wonderful Life (2001)

Music media always loves a tortured soul, and sometimes that’s unfair. The tragic circumstances of Mark Linkous weren’t something to be thrilled about. As much as it’s easy to get detached from the circumstances of artists creating these masterpieces, it’s also unfair the high rate of mental and physical health issues among musicians.

The life of Mark Linkous wasn’t an easy one and, sadly, he killed himself in 2010. A true loss for the music world, he left behind a bunch of incredible albums worth everybody’s attention. It’s hard to pick just one album representing that beautiful sadness that covered his whole career, but I feel confident in putting in front of you It’s A Wonderful Life. A full hour that sums up what made Linkous such a great composer, I hope you enjoy it.

Saddest moment

The references to death in “Eyepennies” are hard to look away from.

Sufjan Stevens – Carrie & Lowell (2015)

A memorial to Stevens’ late mother, Carrie & Lowell was never going to be a happy event. Referring to his mother and her second husband, Lowell, the songs were inspired by family trips they took to Oregon in Stevens’ childhood. By all accounts, Stevens’ relationship with his mother was complex; she suffered from depression, schizophrenia, and substance abuse and abandoned him and his brother on more than one occasion as small children. This record is Stevens’ means of processing his grief, not just from his mother’ passing, but also the myriad complex emotions we’re left with from people who are difficult to love but we can’t help but loving, regardless.

Carrie & Lowell is atmospheric and evocative of the pain and loneliness in the wake of loss, and the need to retrace familiar territory for evidence of the person you love, the need to reinforce they were really here.

Saddest moment

What could I have said to raise you from the dead?
Oh could I be the sky on the Fourth of July? 

The Antlers – Hospice (2009)

In their breakthrough album, The Antlers told the story of the relationship between a hospice worker and a female patient suffering from terminal bone cancer. If this line already sounds bleak for you, you’ll be happy to know that the whole plot of this concept album also plays as a metaphor for an emotionally abusive relationship. Not exactly a party. All the hospital and cancer references give a raw edge to it, too. Even if from the melodic side of things the album reaches pretty sweet heights.

Saddest moment

There are so many heartbreaking moments in this record that there’s even a Reddit thread about it.

The Cure – Faith (1981)

I always have trouble choosing which is the saddest The Cure album. I guess for a lot of people it is , but I’ve always read part of that album as more of a nostalgic vibe than straight up sadness. , sure, super dreadful and meditative at times. But if you ask me, Faith is the one I’ve always found the saddest one. The atmosphere of the record feels like the closest you can get to a coma as a listening experience. Slow, gloomy, gothic…everything about this album after “Primary” is black. Blackest ever black.

Saddest moment

The self-titled song captures perfectly the spirit of the album and is an incredible ending for this record.

This Mortal Coil – It’ll End In Tears (1984)

The debut album by This Mortal Coil could have been quite a Frankenstein. Created by 4AD head honcho Ivo Watts-Russell in collaboration with 4AD producer John Fryer, the idea was to cover the favorite records of Watts-Russell but adapted to the sonic aesthetics of the label.

Performed by some artists of the label such as Cocteau Twins, Lisa Gerrard (Dead Can Dance,) Kim Deal…then assembled with instrumentals created purposedly for the album. Funny enough, a couple of those songs were straight out of 3rd / Sister Lovers by Big Star, another one of the sad albums on this list.

The results of this experiment gave us one of the most beloved records from the eighties. A record that somehow anticipated some of the key elements of shoegaze but with the sound of rock from the seventies still fresh.

Saddest moment

Very few times a cover outdoes the original, but the cover of “Song To The Siren” included in this record sang by Elizabeth Fraser is one of the purest moments in music history.

Vic Chesnutt – About To Choke (1996)

As much as the comments section of most social media these days are a dumpster fire. Sometimes, only sometimes, the comments section of Youtube videos can become a celebration we’re all invited to join. This is what I’m finding with a big smile on my face while revisiting About To Choke: everybody leaving their recollections attached to the incredible legacy of Vic Chesnutt, who sadly left us back in 2009.

The greatest ability of Chesnutt’s music was to take you from the darkest depth to a burst of laughter within seconds. I doubt he would like to be remembered as a tragic figure, he was so much more than that. His major label debut, About To Choke, is solid evidence of this.

I’ll join the Youtube choir: Vic, I still miss you.

Saddest moment

“See You Around” is just pure emotion.

William Basinski – The Disintegration Loops (2002)

It hasn’t been too long . But, that was for a different reasons, and here we are again. Don’t get me wrong, I could talk for the rest of my life about this masterpiece and never get tired of it.

The story behind these loops are well known, but just in case you’ve never heard of it: William Basinski intended to transfer different tapes he recorded in the 1980s to digital in order to preseve their content. When he started with the process, he realized that the tapes were already deteriorated but, instead of trying a different approach, he played those tapes over and over again in order to further contribute to their disintegration. By pure chance, he finished the project on the morning of 9/11 in Brooklyn from where he and his friends watched the twin towers collapse. He filmed video footage of the attack during the last hour of daylight from a roof, and the following morning he played “Disintegration Loop 1.1” as a soundtrack to the aftermath.

Whether it happened unexpectedly or not feels irrelevant when listening to this music. Listening to these tapes disintegrate is a transcendent and unforgettable experience. And thanks to its context, one of the saddest ones as well.

Saddest moment

The moment when you read the history behind the album.

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