40 Saddest Albums of All Time

Pastel Blues
by Nina Simone

Pastel Blues starts out simple, sparse, and sad even though “Be My Husband” should be a celebration. It builds on that tone, introducing complexity throughout. The final track is a 10-minute frenzy that sounds like someone is running from and toward something monumental.

Saddest moment:

It’s hard to imagine anything sadder than “Strange Fruit.” It personalizes a historic tragedy that reverberates to the current day.

Sea Change
by Beck

Sea Change is an unrivaled masterpiece of a breakup album. Heartbreak radiates from this record and his breakup with a longtime fiancée was the major influence for the dramatic shift in tone. Sea Change provides plenty of opportunities to wallow, but as a whole, it’s also strangely uplifting. 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.

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

Pink Moon
by Nick Drake

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

Either/Or
by Elliott Smith

Where some of his later albums 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. It 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 re-emerging on “Cupid’s Trick.” For such a despairing album, Elliott leaves us on a bright note of hope with “Say Yes,” albeit with Smith-style muted hope.

Saddest moment

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

Songs Of Love And Hate
by Leonard Cohen

Few albums evoke winter both in a metaphorical and literal sense as Songs Of Love And Hate does. It’s hard not to fall in love with its melancholic quality and how Leonard Cohen 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.

A Moon Shaped Pool
by Radiohead

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 The King Of Limbs. 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. It’s an absolutely devastating post-breakup statement.

Carrie & Lowell
by Sufjan Stevens

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 as small children on more than one occasion. This record is Stevens’ means of processing his grief, not just from his mother’s passing, but also the myriad complex emotions were left with from people who are difficult to love but we can’t help but loving, regardless.

Saddest moment

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

Berlin
by Lou Reed

When we asked the Discogs community, a lot of people 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. Each and every song doesn’t feel so heavy, but 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.”

For Emma, Forever Ago
by Bon Iver

In 2008, it was hard to foresee the huge success that Bon Iver would have 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, which started — if you ask me — a weird trend for many other musicians to do exactly the same with unequal results. Few albums 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.

Ten Love Songs
by Susanne Sundfør

The title says it’s 10 love songs, but every one of them is about breaking up, falling into terrible relationships, or both. Most of this is masked by poppy, complex music. It’s all beautiful and heartbreaking.

Saddest moment

This is the kind of love that never goes out of style
‘Cause, baby, I know that you’ll always be waiting
And I’ll always want to come back

Zulema
by Zulema

The arrangements, the voice, and the lyrics are deep on Zulema’s first album, especially “American Fruits with African Roots.”  It is a masterpiece of soul music full of melancholy.

Saddest moment

We came from a distant land
Ours lives already planned
We came in ships from across the sea
Never again home we’ll see
And now we become
American fruit
With African roots

American IV: The Man Comes Around
by Johnny Cash

This album embodies the last years of a man who had seen so much hurt in his lifetime. A truly remarkable album.

Saddest moment

The cover of Nine Inch Nails’ song “Hurt.” Impossible to choose just one element of these lyrics to highlight.

Caetano Veloso
by Caetano Veloso

This record was made while Caetano Veloso was living in exile in London during the early 1970s. He was arrested by a military dictator’s government under the huge sun of Bahia, Brazil and moved to foggy London to escape that terrible regime. The record is written mostly in English with deep melancholia and I think it will make sense for listeners abroad.

Saddest moment

The song “Maria Bethania,” which was written as an homage to his sister (the singer Maria Bethania) and is asking her to send him a letter from Brazil.

Blackstar
by David Bowie

Everything about 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. 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

Donuts
by J Dilla

Donuts was finished on an MPC in a hospital while battling Lupus, a rare blood condition that tragically took his life at 32, four days after the release of the album. It is now regarded by many as one of the greatest hip-hop albums of all time.

Saddest moment

I’ve got to choose two. First is his flip of Dionne Warwicks’ “You’re Gonna Need Me,” hauntingly poignant and truthful. Second is the mind-melting “Don’t Cry,” which masterfully turns a two-step soul record by The Escorts totally on its head, yet with a sincere undertone. Dilla Dilla Dilla, Beats Beats Beats.

3rd
by Big Star

Part of what makes the third and last album by Big Star such a heartbreaking one is knowing the details of its release. After not succeeding commercially with #1 Record and Radio City, this album was recorded in 1975 then slated by the company until it was finally released in 1978. By that time, Big Star was no more and the album was met with apathy by both audience and critics. 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 1970s.

Saddest moment

It’s hard not to weep when Alex Chilton sings in “Holocaust”:

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

I See A Darkness
by Bonnie “Prince” Billy

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 many others, it’s 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

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

Moon Pix
by Cat Power

How much devastation are you able to stand? This question is an important one to ask before playing Moon Pix. For many, it’s the best collection of songs by Chan Marshall, and that’s a lot considering 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 delivering 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. However, the verses on “He Turns Down,” a song about being rejected by God, have always stuck with me.

The Disintegration Loops
by William Basinski

William Basinski intended to transfer different tapes he recorded in the 1980s to a digital format in order to preserve their content. When he started with the process, he realized that the tapes 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. Listening to these tapes disintegrate is a transcendent and unforgettable experience. And, thanks to its context, it is one of the saddest ones as well.

Endless Skies
by Ashbury

Beautiful guitar harmonies and a soft voice create these sad melodies that, from the first song, enter your mind and leave you breathless till the end. “Madman” is absolutely the saddest song I have ever heard. The lyrics and the music let you perfectly imagine the madman running in the rain and how is feeling. Magical and mystical, it creates amazing epic harmonies.

Saddest moment

So, madman, run from the screams in the darkness
Madman, run from the fear in the night
Madman, run from the power of the lawman
Take another look at your life
Oh, you’re just a madman

No Snare
by Tender Forever

Breakups always fuel the best cathartic sound experiences. Tender Forever’s 2010 release No Snare is about pulling yourself out of the ashes after being in love. The title of the album is calling out the deliberate removal of the snare drum, a symbol of removing the heart from the body. While some of Tender Forever’s songs carry the sweetness of pop music, the orchestral undertones of timpani drums feel like heartbeats and the strings and droning synths like long deep sighs. This album is a beloved companion to the oscillation between sadness and perseverance that accompanies heartbreak.

Saddest moment

This heart is not for you
And it is meant to deal
With the whole part of my life
That you won’t get to feel

Desertshore
by Nico

Desertshore is such a raw piece of music history. For Nico, it would have been easy to remain an appendix to The Velvet Underground history. But she was much more than that and she was ready to prove it to the world. Desertshore is so passionate and 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). Also, how many other artists get their albums reworked by Throbbing Gristle?

Saddest moment

You are beautiful and you are alone

White Chalk
PJ Harvey

It’s a sharp departure from its predecessor, Uh Huh Her (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 and 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.

Saddest moment

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

Unknown Pleasures
by Joy Division

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. Decades later, 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.

Turn On The Bright Lights
by Interpol

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.

A Crow Looked At Me
by Mount Eerie

No list about sad albums can do without A Crow Looked At Me. None. Phil Elverum’s wife, Geneviève, died in 2015 of pancreatic cancer four months after the birth of their first child. 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.

Saddest moment

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.

Frigid Stars LP
by Codeine

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. It’s emo before emo existed. Raw, emotional, and evocative, Frigid Stars LP remains as one of the best albums of the genre and it will keep bringing us down for many decades to come.

The Sophtware Slump
by Grandaddy

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.

Ruins
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. 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.

James Blake
by James Blake

James Blake took the world by storm with this debut album. A new way of making music showcased his sensibilities to the world and the album was an instant hit. 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.

I Could Live In Hope
by Low

Both I Could Live In Hope and Things We Lost In The Fire 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.

Ghosteen
by Nick Cave & The Bad Seeds

Nobody can be emotionally prepared for this album. After the incredibly sad and unforgettable Skeleton Tree, 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.

Dummy
by Portishead

Portishead’s genre-bending, widely revered debut album is often attributed with taking trip-hop mainstream. Even 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 works together so well. Despite being a critical darling, the sad core of this album really creeps up on you.

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.

Down Colorful Hill
by Red House Painters

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 1990s. Very few times the artwork of an album matched so perfectly the mood of its music. We have to thank Mark Kozelek for a whole career of heartbreaking music. So no, we haven’t forgotten about Benji.

Saddest moment

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

The Doctor Came At Dawn
by Smog

With a career spanning three decades, Bill Callahan (AKA 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. 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.

Ghost Tropic
Songs: Ohia

Ghost Tropic is 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.

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.

It’ll End in Tears
by This Mortal Coil

The debut album by This Mortal Coil could have been quite a Frankenstein monster. 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 label artists such as Elizabeth Fraser (Cocteau Twins) and Lisa Gerrard (Dead Can Dance), it was assembled with instrumentals created purposely for the album. The results of this experiment gave us one of the most beloved records from the 1980s, a record that somehow anticipated some of the key elements of shoegaze. A couple of those songs were straight out of 3rd by Big Star, another album on this list.

Saddest moment

Very few times does a cover outdo the original, but the cover of “Song To The Siren” by Elizabeth Fraser is one of the purest moments in music history.

It’s A Wonderful Life
by Sparklehorse

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. A true loss for the music world, Linkous 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.

Saddest moment

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

Hospice
by The Antlers

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. Even if from the melodic side of things the album reaches pretty sweet heights.

Faith
by The Cure

I always have trouble choosing which is the saddest The Cure album. For a lot of people, it is Disintegration, but I’ve always read part of that album as more of a nostalgic vibe than straight up sadness. Pornography is 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 bleak.

Saddest moment

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

Editor’s note: Thank you to the entire Discogs team for contributing to this list of sad albums over the years. We couldn’t have cried together without you.