Five of the saddest songs of all time


Many of the world’s greatest songs are also some of the saddest. But what makes a song sad, and is a sad song necessarily depressing? Furthermore, are songs that juxtapose a cheerful melody with dark lyrics still sad? Are songs with sad music but optimistic lyrics joyful? To my ear, the score sets the tone and mood, regardless of the verbal content. Generally speaking lyrics contain only semantic content, whereas the music is the emotional component that imbue the words with their full, human meaning.

If one takes a look at a printed song lyric, it can come across as rather silly and trivial, while it in its proper context may feel both impassioned and expressive. It’s not always the words themselves that are of the biggest importance, but rather how the words are sung. The true meaning of the words comes to light only in their correct backdrop.

However, I think it’s safe to say that these songs, five of the saddest I know of, all have music and lyrics that both are on the same despondent level. I thought it would be interesting to make such a list, and this is of course a highly subjective compilation.


Red House Painters – Katy Song (Red House Painters, 1993). To the best of my recollection, it was back in 1999 that Laura, an American friend of mine, introduced me to the Red House Painters with their song New Jersey (the re-recorded version). From then on I was hooked on Mark Kozelek’s eerie vocals, his honest, introspective and deeply personal lyrics and the distinguishable, slow-paced music (All Music Guide actually label their music as “Sadcore,” which I find a bit funny).

Red House Painters is one of few musical acts that it only takes seconds to identify, since their music is unique and no one else sounds quite like them. In fact, when I saw Vanilla Sky in 2001 and a version of Have You Forgotten that was recorded especially for the movie could be heard low in the background in one scene, I instantly recognized that it was Mark Kozelek behind the microphone.

One could argue that a harrowing track like Uncle Joe exudes more melancholy than Katy Song. After all, few other recordings are as downhearted and as blunt in its despair and desperation: “Where have all the people gone in my life? / I’m looking at the ceiling / With an awful feeling of loss and loneliness / The after late night television pain / I’m running out of strength.” Medicine Bottle off 1992’s Down Colorful Hill is perhaps equally gloomy, as it acutely recounts a collapsed relationship (“The hurting never ends / Like birthdays and old friends”) against a doom-laden musical backdrop. However, I still picked Katy Song because of such forlorn and beautiful lines as these:

I know tomorrow you will be
Somewhere in London, living with someone
You’ve got some kind of family there to turn to
And that’s more than I could ever give you

A chance for calm
A hope for freedom
Outlet from my cold solitary kingdom
By the forest of our spring stay
Where you walked away
And left a bleeding part of me
Empty and bothered, watching the water
Quiet in the corner, numb and falling through
Without you what does my life amount to?


The Shins – A Comet Appears (Wincing the Night Away, 2007). I didn’t discover The Shins until I heard them on the soundtrack to cult movie Garden State in 2004. I was instantly infatuated with New Slang, and I just had to hear it again and again. It’s still one of my all time favorite songs. When their latest album Wincing the Night Away was released in 2007, I was initially a bit disappointed, even if I came to appreciate it more with time (it’s a great record to fall asleep to). However, one song that instantly moved me was the tragic ending track: A Comet Appears. I wish I could quote the entire lyrics, because they are excellent, but here is an illustrative excerpt.

Close your eyes to corral a virtue
Is this fooling anyone else?
Never worked so long and hard
To cement a failure

We can blow on our thumbs and posture
But the lonely is such delicate things
The wind from a wasp could blow them
Into the sea, with stones on their feet
Lost to the light and the loving we need

Still to come
The worst part and you know it
There is a numbness
In your heart and it’s growing


The Velvet Underground – Heroin (The Velvet Underground & Nico, 1967). This classic song depicting heroin addiction is one of the Velvet Underground’s most highly-esteemed compositions, and it was written by Lou Reed in 1964. While the song only has major chords, the lyrics are heartrending.

…I wish that I was born a thousand years ago
I wish that I’d sailed the darkened seas
On a great big clipper ship
Going from this land here to that
On a sailor’s suit and cap
Away from the big city
Where a man cannot be free
Of all the evils of this town
And of himself and those around

Oh, and I guess that I just don’t know
Oh, and I guess that I just don’t know

Heroin, be the death of me
Heroin, it’s my wife and it’s my life
Because a mainer to my vein
Leads to a center in my head
And then I’m better off than dead…


Elliott Smith – I Didn’t Understand (XO, 1998). When it comes to sad Elliott Smith songs: take your pick. The songwriting singer, who died from a (self-inflicted?) stab wound to the chest in 2003 at age 34, might have claimed in interviews that there’s plenty of joy in his music, and that the sadness partly is there to provide a contrast to the happiness in order to underline it.

A few of his songs might be a bit on the sunny side, but even the more upbeat tracks still have themes that revolve around mental illness, depression, loss and addiction. I don’t think I know of an artist that has been more consistently downhearted in both lyrics and melody. He’s also probably the composer of popular music I admire the most: his work is often brilliant and distinctive, with exquisite, well thought-out chord changes, poetic lyrics, excellent arrangements and soft, whispering vocals. I’ve been in awe since Good Will Hunting.

Songs like Sweet Adeline (“It’s a picture perfect evening and I’m staring down the sun / Fully loaded, deaf and dumb and done / Waiting for sedation to disconnect my head / Or any situation where I’m better off then dead”) tell tales of despair, addiction and doing anything to escape the burdening realities of life. He has also written some of the greatest love songs of all time, Say Yes (“I’m in love with the world / Through the eyes of a girl”) and Between the Bars; his signature track:

Drink up, baby, stay up all night
With the things you could do, you won’t but you might
The potential you’ll be that you’ll never see
The promises you’ll only make

Drink up with me now and forget all about
The pressure of days, do what I say
And I’ll make you okay and drive them away
The images stuck in your head

People you’ve been before
That you don’t want around anymore
That push and shove and won’t bend to your will
I’ll keep them still

Drink up, baby, look at the stars
I’ll kiss you again, between the bars
Where I’m seeing you there, with your hands in the air
Waiting to finally be caught

Drink up one more time and I’ll make you mine
Keep you apart, deep in my heart
Separate from the rest, where I like you the best
And keep the things you forgot

People you’ve been before
That you don’t want around anymore
That push and shove and won’t bend to your will
I’ll keep them still

It’s impossible to pick Elliott Smith’s saddest song, and there’s really no point in doing so either. Let’s Get Lost (“Burning every bridge that I cross / To find some beautiful place to get lost”), A Fond Farewell (“I can deal with some psychic pain / If it’ll slow down my higher brain / Veins full of disappearing ink / Vomiting in the kitchen sink”), King’s Crossing (“Every wave is tidal – if you hang around you’re going to get wet / I can’t prepare for death any more than I already have”) or Waltz #2 (“She appears composed, so she is, I suppose / Who can really tell? She shows no emotion at all / Stares into space like a dead china doll”)?

Finally, almost randomly, I picked I Didn’t Understand from Elliott’s 1998 album XO.

Thought you’d be looking for the next in line to love
Then ignore, put out and put away
And so you’d soon be leaving me
Alone like I’m supposed to be
Tonight, tomorrow and everyday

There’s nothing here that you’ll miss
I can guarantee you this, is a cloud of smoke
Trying to occupy space
What a fucking joke, what a fucking joke

I waited for a bus to separate the both of us
And take me off far away from you
‘Cause my feelings never change a bit
I always feel like shit
I don’t know why I guess that I “just do”

You once talked to me about love
And you painted pictures of
A never-neverland
And I could’ve gone to that place
But I didn’t understand
I didn’t understand
I didn’t understand


David & the Citizens – Something, Not Sunlight (For All Happy Endings). This song from the early 00’s by now defunct Swedish indie outfit David & the Citizens may not have obviously sad lyrics, but it’s without a doubt one of the most desperate songs I know of; the vocal performance and the music really scream of despair, and towards the end it explodes in grief and utter hopelessness. Apparently, the song is about the singer’s loss of his mother. I think listening to this recording almost can be a physically painful experience at times.

Now we scream in the car
Just because no one can hear it
And no one can say it’s dumb
Another day gone and done

Like something, not sunlight

I move the spoon slowly
The rain hammers on the street
A feeling that just won’t pass
The question still stands

Like something, not sunlight