50 of the saddest songs of all time

50 of the saddest songs of all time

I've been putting this one off for a while, simply because I've just been trying to be a bit more creative than listing sad songs, which realistically makes up the majority of my music library. But I've decided to just bite the bullet and do it, so here we are. There's a good mix in here as always, the majority are indie but I've chucked the odd rock, metal and pop song in there for the fun of it. Not every one of these is the most obviously devastating song (although there are plenty that are), but in their own way each one is truly heartbreaking. I've tried to stick to one song per artist but in a few places this just wasn't possible, but who cares? Just a quick content warning, there are mentions of mental health issues, suicide and drug use/ abuse, so just watch out in case you're sensitive to that. As always there's a playlist to go with the list, as well as my larger sad songs playlist linked. So in no particular order, let's get started. 

Attic Basement - A Werewolf

Whilst the production could be a little sharper, the slightly dull bass guitar really contributes to the rainy-day feel of 'A Werewolf'. A song about trust and sacrificing things in order to make a relationship work, this isn't the most obviously tragic song but just something about the way 'I can be a werewolf, if you want me to' just rings so true of a relationship where you'll do anything, including becoming someone you aren't, to keep it alive.

Phoebe Bridgers - I know The End

I've seen quite a few other Bridgers songs on similar lists and while I can see why this one isn't often an addition to these lists, something about beautiful introduction and hauntingly aggressive ending give such a feeling of bittersweet closure. Not to mention the truly devastating 'The end is here', managing to be both uplifting and yet funeral-ish all in one fell swoop.

flora cash  - You're Somebody Else

This beautiful track did the rounds on TikTok a few months ago, and while that can sometimes result in the song being a bit ruined (See Greek Tragedy by the Wombats), in this case it simply served to circulate the song more widely. Another one about becoming somebody that you're not, the background distortions and fluttering strings giving a sense of discomfort akin to this feeling, it's simple but layered and beautiful. 

Damien Rice - Delicate

I first heard this in a truly tragic scene in Misfits, which works so perfectly to tie the entire scene together, but still works outside of the context of it, being so calm and soothing yet so sad. The title is so fitting to how beautifully gentle and authentic the track is, softly lulling through the runtime and just so softly devastating you.

Radiohead - Videotape

I could easily make this list just songs by Radiohead, The National and Bon Iver songs, so to choose just one (or two) by the former was incredibly difficult. But something about Videotape just stands out above the rest, the gently plodding keyboard, fluttering persistent electronics in the background and so straight-forward and raw vocals just grip me from start to finish. The extended outro may be a bit repetitive but it closes the song out beautifully, drawing it to a finish by subtly removing one element at a time just leaving the sound resonating. 

Vancouver Sleep Clinic - Someone To Stay

 Minimalism is probably the best way to get me to describe a song as beautiful, yet this song does the exact opposite, throwing element after element on top of one another (which under different production can easily lead to a cluttered sound) to the point where it sounds nigh-ethereal and manages to feel both uplifting and brutally sad depending on your emotional state. Most of the bands' back-catalogue isn't really worth much of a listen, but this one will be difficult to keep off playlists. 

Bon Iver - Blood Bank

Again it was so difficult to choose from Bon Iver's discography, with his signature sound basically being ultra-melancholia and heartache. But I've chosen what is essentially an outtake from For Emma, Forever Ago, being written in the same post-breakup cabin-isolation writing session by Justin Vernon, which I honestly can't understand how it was cut from the main release. That aside, 'Blood Blank' is a harrowing track about mortality (at least from my interpretation) that I would do just about anything to hear live, and probably cry to hear. 

Slaughter Beach, Dog -104 Degrees

A track that's fairly obviously more about the lyrics than the music, the latter being a simple set of instrumentations that lay a foundation for the subtle yet emotional vocals. Even though nothing about this song is overtly sad it manages to bring me right down every time I hear it, somehow it just feels like such a mundane sadness, far more relatable than the melodramatic kind so often seen in a lot of sad songs. 

Flatsound - I exist I exist I exist

Through writing this list I'm realising that the tracks that really pull on my heartstrings aren't those that slap you in the face with sadness, not ones that just say 'Oh I'm dying. that's sad' (although these obviously still hit me) but it's just the ones that creep up on you after a few listens till you realise quite how brutally melancholic they are. This cut is a perfect example of the latter, so musically simple, calming and nigh on hypnotic but every single word cuts like a knife. 

Keaton Hanson - You Don't Know How Lucky You Are

The feeling that the person you love may be better off with someone else but still you just don't quite want to let them go because they're yours and you know how to be with them just right? Yeah that'll do it.

The Hotelier - Your Deep Rest

Emo is fairly obviously overwhelmed with sad songs, with the majority of the genre's lyrical contents being fairly depressing and melodramatic. But even by Emo's standards this modern classic from The Hotelier is up there with some of the most tragic, looking at someone who feels guilt surrounding his friend's death to the point where he can't even go to their funeral or look their family in the eye. This was one of the first Emo songs I fell in love with and therefore it has a bit of a special place in my heart, but good God that's for a good reason. This cut is as headbang-inducing as it is heartbreaking.

Against Me! - Two Coffins 

On a record about transgender dysphoria and the depression that the lead singer experienced in the midst of her gender transition, it's no surprise that there's a track here and there that bog you down a bit. The surprise comes from how simply beautiful the song is, no punk band has the right to be quite this effortlessly stunning and melancholic. Employing an incredibly simple acoustic guitar melody, drums and echoey vocals the band create a truly incredible ballad about death. 

Daughter - Medicine

I won't lie I'm going to struggle to write much on this one, a track about the dangers of addiction but always feels a bit of a comfort to people on antidepressents this song is just so fucking heartbreaking. and that's that.

Johnny Cash - Hurt

I couldn't decide between this and the original by Nine Inch Nails, and while they both have their merits, the industrial-ballad from the latter giving an edge to the track. But something about the rawness in Johnny's vocals, the fact he recorded it not long before his death, the pure bliss he sounds in despite the morbidity of it and just how beautifully gruff and tragic he sounds, almost like he's choking back tears at every line. 

Snow Patrol - You Could Be Happy 

From the same album as the absolutely euphoric and incredible 'Chasing Cars' is a self-deprecating ballad about choosing someone else's happiness over your own. Yeah yeah Snow Patrol are a bit out of it and stale but there's no doubting the simplistic beauty in this cut. 

Brand New - The Boy Who Blocked His Own Shot

Back we go into the land of Emo, once again without the eyeliner and melodrama, a delicate and intimate acoustic track with a storyline I've never been able to follow too well. Every time I listen I hear extra little details, like the stunning vocal layering, slightly canonized and echoey acoustic guitar and tiny little sound effects. Much of Emo hasn't stood the test of time, but that can't be ever said of this classic.

Los Campesinos - The Sea Is A Good Place To Think Of The Future

Another track about truly bleak subject matter - a girl trying to avoid an eating disorder, trauama and depression by experimenting with drugs until she overdoses, yeah it's not an easy listen sometimes. But when you're up for it it hits like a baseball bat, the monotone delivery of the vocals with the randomly interspersed hyper-layered and autotuned harmonies just colliding together into one big wall of sound and sadness.

Okkervil River - A Stone

Folk often has some of music's best storytelling, and this track proves that in the best way possible, telling a somewhat nonsensical story of unrequited love through beautiful metaphors and lyricism. So weird yet so stunning.

The National - About Today

A friend of mine once skipped through this song trying to find some vocals but all he got every skip was instrumentals, which is really what makes this song so incredible. It just makes the 'Well can I ask you, about today' all the more absolutely devastating when they eventually come. This is up there on my bucket list of songs to hear live. 

Jeff Rosenstock - I'm Serious, I'm sorry

So deceptively upbeat this cut's seemingly a mix of stories about suicide, regret and just general horrible life experiences. Somehow it's all tied together into a track that gets your headbanging no matter how close to tears you may be. 

Ed Sheeran - Small Bump

Okay okay, I know Ed Sheeran is pretty crap, he's annoying, tries to rap when he can't plays fairly boring and generic music and is just everywhere for some reason. Having said that, an admittedly beautiful song about a miscarriage deserves to be on this list, it's absolutely heartbreaking and so irritatingly good. 

Neil Young - Only Love Can Break Your Heart

This one can depend a bit on the mood you're in and your current relationship status, it can either be a hopeful ode to the power and beauty of love and why it's worth having. Or it can be a melancholic ballad about how brutal and painful it can be when it doesn't quite go to plan. Either way, it's a classic that feels as fresh now as it did when it was over 50 years ago. 

LCD Soundsystem - New York, I Love You But You're Bringing Me Down

For a musician primarily geared towards dance music, James Murphy has a real knack for making really quite sad music, especially for people in their mid-30s in New York. While this one sits more on the side of indie than dance, he's still flexing his melancholic muscles to great effect in a simple and timeless cut. And for anyone who hasn't seen the Miles Davis improvisation overlay on the song needs to check it out now, it's stunning.

dandelion hands - How To Never Stop Being Sad

Spoken word has a very mixed reception, often it can be a bit drab and pretentious without providing much sonically, but I think this is a great example of how it can be really fantastic. The faint electronic throbbing underneath the monologue of self-deprecation make for a truly fantastic piece all about self-help and mental health in general. 

The Verve - The Drugs Don't Work

From the band with that orchestral song, (really interesting story behind the rights to that here) comes one of the nation's tear-jerking anthems. While the official interpretation of this song is that it's about Ashcroft's dad's death from cancer, I've always taken this more in the direction of depression or even recreational drugs failing to give the pleasure needed from life. Either way, it's absolutely fantastic and harrowing.

Larry Pink The Human - Love You, Bye

I truly believe that electronic music is by far the most difficult genre in which to make a sad song, something about it just so infrequently lends to the tone whilst still actually being a good and listenable song. So to hear someone in 2020 master this was an absolute revelation, and put Slaves' guitarist Laurence Vincent's solo project on the map and at the top of my to-watch list. Managing to be both beautifully produced and yet still emotionally raw, Love You, Bye is a testament to how good the new indie scene is.

MF Doom - That's That

I'm ashamed to say I only got into MF Doom after his passing last year, and while not all of his catalogue is quite to my taste I am absolutely floored by his talent. The incredible flow, rhymes and beats make this a completely captivating and nearly hypnotic listen, laced with a beautiful sadness that I can't quite put my finger on. 

Bon Iver - Holocene

To only put two Bon Iver songs on was hard enough, with the likes of For Emma, Forever Ago, Hey Ma and Skinny Love not quite making the cut, but I just had to put this one on. I haven't given the Sophomore album from Bon Iver the time it deserves, but I think I've spun this track enough times to make up for it, because it is an absolute masterpiece. Showing Vernon begin to transition into a slightly more electronic, auto-tune-utilising sound but still weaving in the classic acoustic folk sound, Holocene is without a doubt one of the prettiest and saddest tracks I've heard. 

Regina Spektor - Eet

I'll be hones I have no idea what she's on about or quite what makes this song so great, but it is, there.

Bakar - Unhealthy

One of my biggest regrets from Reading Festival 2019 (that I can actually remember and mention) was not seeing Bakar live, I didn't really discover him until the weekend after the festival. This song is proof of what makes him just so fantastic, an incredible and catchy beat, flow and delivery with a very solemn spoken word section in the middle. What brings me down on this track is just the dull acceptance of sadness that's in it, but so perfect.  

Elliott Smith - Between The Bars 

Obviously there was going to be an Elliott Smith song on here, and I know this is probably the most obvious choice out of his discography but come on, its absolutely devastating. I can't bring much original thought to Smith's work as one of the most well-loved and written about songwriters of all time, but I will just say that this song has the ability to bring me to tears far too easily.

My Chemical Romance - Cancer

This song feels a bit out of place on the powerhouse that is The Black Parade, despite being about one of the largest causes of death - the entire theme of the album. Despite that, the monologue of a man on his death bed talking about leaving his love is undoubtedly tragic, and just such a well-written song. Twenty One Pilots gave it a crack but just didn't quite have the passion behind it.

The Lumineers - Slow It Down

There's something so incredibly and unassuming about this cute from the Delilah boys, whereas their main single is blatant about its intentions, this track manages to just creep up on you slowly over the course of the song, sleepily lulling you. 

Sia - Breathe Me

One of the most stunning vocal performances of all time, taking a somewhat bland song and making it a truly fantastic listen simply down to Sia's stunning voice.

Band of Horses - The Funeral

Anyone familiar with How I Met Your Mother will know this track very well, and as a result may have positive associations with the song due to the edited version featured in the show. The standalone track is a little slower and sadder, but no matter which version you listen to it is a completely flawless cut that is one of the most enthralling and immersive listens.

Mac Miller - Good News

There's very little about this song that makes it stand out too much (beyond Miller's classic unique beat and flow), it's fairly standard for his style and fits in well with his discography. However, the simple fact that this was released a few weeks after his death detailing the way he was feeling not long before it makes it truly tragic and stunning.

M83 - Wait

Again showing off an electronic group managing to be emotional, the French duo have crafted one of the best dream pop songs of the 2010s. I don't have too much to say except get a good pair of headphones and stick this on loop, enjoy. 

Blue October - Hate Me

The intro to this song is an actual recording of the lead singer's mum calling him when he was going through addiction and general mental health issues, something I just can never imagine having the balls to do. One of the few tracks on this list that's not slow and definitely upbeat enough to mosh to, despite also having the ability to bring tears to your eyes. 

The Streets - Never Went To Church

For The Streets I couldn't quite decide between this, Dry Your Eyes or It's Too Late, but ultimately Skinner singing about the death of his dad just seemed like it couldn't quite be beaten. While it may not be the Streets' best song, and its album is definitely on the weaker side of the group's discography, there's something so authentic about it that so few hip-hop artists manage to achieve, especially with this level of lyricism. 

The Wonder Years - Cigarettes and Saints

The Wonder Years have become an iconic band in modern Scene, crafting a unique sound with raw and authentic vocals, lyrics and production style merged with a highly energetic and catchy musical style. This cut tells the story of the lead singers' friend's overdose and the grief surrounding this, complex feelings that are pulled off in an incredibly effective and sensitive way, just cementing the band as a group with a highly successful future. 

Architects - Hereafter

For a while 'Snuff' was taking this spot on the list, but when I listened to this again the lyric 'I'm fighting with broken bones' just stuck with me in such a strong way that it felt impossible to leave it off. One of many songs from the band chronicling their battle with grief after the death of former lead-songwriter Tom Searle, all tied together with signature Architects ferocity.

Joy Division - Atmosphere

You'd be hard pressed to find a genuinely happy Joy Division song, even the more upbeat 'Love Will Tear Us Apart' isn't all sunshine and rainbows, so it's no surprise that they've managed to sneak on to this list. The quaintly minimalist 'Atmosphere' may have a twinge of hope laced through its chord progressions, but something about the 'Walk in silence' makes it feel more like Curtis writing his own funeral procession than a genuine glimpse of optimism.

The 1975 - Robbers

One of the songs that gained Matty Healy's crew fame, and for good reason, Robbers is one of the band's absolute best that still appears at pretty much every single live performance and feels as relevant to the band's sound as it did when it came out. Toxic relationships are often difficult to portray with much sensitivity and yet Healy has managed to do this (subtlety not always being his strong suit) with such ease. 

The Smiths - Asleep

I'm in no way saying this is the best Smiths song, as I believe that title goes to 'Girlfriend in a Coma' and it's probably not the most obviously sad from the group, 'Heaven Knows I'm Miserable Now' jumps to mind. But there's a certain quietness, a lack of pomp and attention-grabbingness that so many of the band's cuts have, in 'Asleep' that just makes it stand out above the rest.

Llojd - Hjorthagen 

Look I have no bloody clue what this song is about but it's incredible, sad and stunning and that's what matters.

Sun Kil Moon - Ben's My Friend

Who knew that lyrics such as 'Blue crab cakes, blue crab cakes, blue crab cakes' could be the soundtrack to a truly heartbreaking midlife crisis quite so well. Notes of sadness, humour and existentialism lace this incredible well-told story about the realisation of the singer's situation in life, bringing to life the perfect but admittedly monotone vocal performance. 

Pedro The Lion - Options

So often love and relationships are overly romanticised in music, or at the very least overexaggerated and dramatised. This does the opposite, depicting a struggling marriage where neither party is quite willing to call things as they are and hanging on for the sake of titular 'options'. While it is a somewhat sweet story about choosing to commit to someone, the bleak reality of the love slowly dying with neither able to escape is really quite sombre. 

Burial - Archangel

Once again showing off the more sensitive side of electronic music, this time leaning far more heavily into the electronics than previously on this list. Minimalism is arguably one of my favourite musical styles, and this track masters it to a perfection, looping and sampling the same phrases over and over to within an inch of their life, yet still carving a melodramatic and emotional cut.  

Radiohead - How To Dissappear Completely

I struggle to think of any Radiohead track any sadder than this, despite their entire catalogue essentially being a mission to depress their fanbase as utterly completely as they can manage. But this one takes the cake, blending beautifully delicate electronics, acoustic guitars and soft vocals to absolute perfection. To some people, Kid A was lacking a bit of soul in favour of pure experimentation, but it is hard to deny the heart in this one.   

The Broken Family Band - It's All Over

Bringing this list to a very apt finish is my most listened song of all time, and one that I would struggle to ever not put in my top 5 songs of all time. The delicate and sparse lyricism, building and crashing instrumentals, catchy melodies and sublime but rough production style create what is simply one of the best songs I have ever heard. So simple yet intricately detailed, every time I listen I manage to hone in on a different element of the track and makes me feel a completely different emotion to the last listen. I will simply never tire of this song, no matter how utterly devastating it is each time. 

Hopefully this list will give you some good material for the blues, but also not bring you down too much. 

Here's the wider sad songs playlist

And here's the playlist for this list 

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