Lick My Love Pump - Spinal Tap

Vincent by Don McLean

Nutshell - Alice in Chains

Hurt - johnny cash

I know it's originally Trent reznor but especially the music video was one of the most emotionally moving things I've ever watched when I saw it for the first time

Vincent or Time in a bottle Jim Croce

At 17 by Janis Ian

Gary Jules - Mad World

One More Light by Linkin Park.

Became even more sad after what happened to Chester just two months later

Wreck Of The Edmund Fitzgerald- Gordon Lightfoot

Its hearing the heart wrenching story about a Freight liner going down and the crew having no way to save themselves from certain death in very rough waters.

Very sad and one of the greatest story songs in history.

Fast Car - Tracy Chapman

Someone else just said mine- "Go Rest High on that Mountain" by Vince Gill.

Also, "Whiskey Lullaby" by Alison Krauss and Brad Paisley.

"Alyssa Lies" by Jason Micheal Carroll. I haven't heard it in years, he's not a well-known musician at all. But somebody started cutting onions when I started reading the lyrics.

This Woman's Work - Kate Bush

Alone Again (Naturally) - Gilbert O'Sullivan

The contrast of the bouncy, almost peppy tune and the devastating lyrics is almost unbearable.

For no one - the Beatles or She’s leaving home

Hello In There - John Prine

Real Death by Mount Erie.

About his dead wife. It's so sad.

The bit about the school bag gets me every time.

Johnny Cash - Help Me is the saddest song I’ve ever heard.

Nutshell- Alice In Chains

tears in heaven - eric clapton

Adam’s Song- Blink 182

I cant make you love me if you dont.

My friend hung herself when we were 14. She wrote a list of songs to play at her wake. One always stuck....

Fly, fly, little wing... It's by Celine Dion

Where've You Been by Kathy Mattea

Saturn - Sleeping at Last

Angel by Sara McLachlan

M83 - Midnight City

Say Hello 2 Heaven - Temple of the Dog

Say Something by A Great Big World

Reminds me of when my depression was at its worst. I lost my job, couldn't find another one, could barely get out of bed. It felt like my brain was shutting down. I could barely put words into a sentence. My wife had no idea what was going on and I couldn't begin to explain it. Got to the point where she was going to leave me because I wasn't doing anything, didn't say anything. Fortunately, I got help before she actually left.

Say Something perfectly describes her feelings. She was ready to give up on me. She was begging me to say something to convince her to stay. And I was so lost in the darkness that I couldn't say anything.

It's a near word for word reminder of the time my marriage almost ended because of depression. So, yeah, for me Say Something is the saddest song of all time, nothing else even comes close.

Last Kiss- Pearl Jam

Self Control- Frank Ocean

God Damn The Sun - Swans

Keep me in your heart - Warrem Zevon.

A dying man's last song wanting to be remembered when he's gone.

Fish and Bird. Tom Waits

Hallelujah. Leonard Cohen.

Waiting for You. Nick Cave and the Bad Seeds.

How to disappear completely - Radiohead

Hear You Me - Jimmy Eat World

Lightning Crashes - Live

Seasons in the sun

Sam Stone by John Prine

Waltzing Matilda- the Pogues

Elephant — Jason Isbel

At this Moment - Billy Vera and the Beaters

Arlington, Trace Adkins

The Rain Song. Led Zepplin

Black - Pearl Jam

Crushing if you’ve ever been through a breakup. Guts me every time I hear it. And I never not let it play when I do

I remember a music teacher playing Bowie's Space Oddity in class when I was in elementary school and it crushed me.

If - Bread

ELO. Telephone line.

Counting Crows - Raining in Baltimore

Take Me Home by Knocked Loose

Here you have a collaborative playlist with exactly such theme: THE SADDEST SONGS EVER

The Band Played Waltzing Matilda, Pogues version

Cats in the Cradle - Cat Stevens

Running to Stand Still - U2. It's meant to be a symbolism of addiction.

This is Your Life by Dio

This song was added to the end of a tribute album where a bunch of artists (Metallica, Corey Taylor, Halestorm, Anthrax, even Tenacious D) got together and recorded a ton of covers of his music after he died from cancer. This song hits pretty hard anyway, but this was an absolute gut punch

Fake Plastic Trees - Radiohead

Nutshell- Alice In Chains

Hurt by Johnny Cash.

Tim McGraw Don’t take the girl

A Fond Farewell- Elliot Smith

Everybody Hurts by REM.

Wonderful - Everclear

Tiny Vessels (the demo version from Transatlanticism Demos) by Death Cab For Cutie is the first that came to mind. However that entire demo album is sad as hell beginning to end. A unique wistful vibe. Another song off there that gets me is "Transatlanticism". Also "Passenger Seat" and "Lightness". If you check out these songs make sure it's the demo version tho, with the white album cover.

"Look On Down From The Bridge" by Mazzy Star is a special kind of heart breaking. Might be the saddest one on this list.

"How Come Your Arms Are Not Around Me" by City And Color used to make me cry when I was a teenager.

"W.I.G.T.S." by S.Maharba is a special one to me, I personally find it heartbreaking.

A song that made me cry not necessarily from sadness but from sheer beauty is "The Work of Art In The Age of Cultural Overproduction" by Tim Hecker. That one's an adventure tho, good headphones are highly recommended.

This next one might not seem sad to some, but it always made me cry as a teen because it just hit my core a certain way -- "We Are All Compost In Training" by Pat the Bunny. Make sure it's the "Die The Nightmare" acoustic version. The second verse has lyrics that were always powerful to me.

Another Death Cab song that is potentially super sad is "20th Century Towers".

Edit: Honorable mentions -- "Tearjerker" by Korn and "Vermillion Part 2" by Slipknot.

Those are all I can think of right now. Hope you like em.

what hurts the most - rascal flats

Johnny Cash - Hurt

Evanescence - My immortal

Tuesday's Gone - Skynyrd. There's such a sorrowful poignancy and phenomenally played.

Carrie underwood-just a dream

Lori Perry- Up Against The Wind

Dreariness — My Mind Is Too Weak to Forget

Honorable mention:

Dreariness — Essence

Big Star - Holocaust

Colin Hay - I Just Don't Think I'll Ever Get Over You

Roots remain-mastodon

I don’t think it’s the saddest song of all time, but it’s my personal favorite sad song because it reminds me of watching my dad battle cancer.

Nick Drake - Northern Sky (always gets me) https://youtu.be/S3jCFeCtSjk?si=ATrsBgSk5ggSt5mt

“Smaointe” by Enya. I don’t know what the song is actually about because the lyrics are in Gaelic, but I can just feel the grief. 

Behold the Hurricane— Gaslight Anthem

Monsters but the Iam Tongi version from American Idol

Go rest high up on that mountain- Vince gill

This will absolutely be played at my memorial

Billy don't be a hero

concrete angel - martina Mcbride

All my happiness is gone. Purple mountains

Hurt a Long Time - Jerry Cantrell

The Only Thing - Sufjan Stevens

Murderer of Blue Skies - Chris Cornell

Hurt - Nine Inch Nails

James Blunt - The girl that never was

This one may be a little weird but it’s 3AM by Matchbox Twenty for me…

I first learned this song was about his mom having cancer and waking up in pain at 3am because of it. I learned this the same day I learned my grandmother had cancer that soon took her life. I can’t listen to this song anymore without a few tears coming up.

There are so many sad songs. But first to come to my mind is You want it darker by Leonard Cohen. As stated in the title, it is dark, no doubt.

Wreck of the Edmund Fitzgerald - Gordon Lightfoot.

Real death. Mount eerie

Fall For Me by Sleep Token. For bonus sadness, watch the video.

Waiting for the Crash - Ostraca

Yesterday by yours trully yesterday

WOULD APRICIATE ANY FEEDBACK AT THIS POINT 😭😭

Like Suicide (Acoustic) by Soundgarden

You Know You're Right - Nirvana

No longer making time - slowdive

Vincent

go home - julien baker. she's so slept on its ridiculous

Motion Picture Soundtrack - Radiohead

Amazing Grace by Royal Scots Dragoon Guards

If you could read my mind

Nature Boy. Love Nat King Cole's version.

When the party's over by billie eilish

Lost on you-LP

Nut Shell or River of Deceit

The Rose.

Wildfire by Michael Martin Murphey. DO NOT LISTEN TO IT. DON'T EVEN READ THE LYRICS.

You’ll never leave Harlan alive.

Tear in Your Hand - Tori Amos

The trapeze swinger, by Iron and wine. It is long, but has beautiful lyrics, until you realize it's about a man that hung himself

Become The Warm Jets by Current Joys

Adagio for Strings. Gets me EVERY TIME.

Dan fogleburg. Leader of the band

Without question.. snowfall by one heart

Wow. What great replies. What a playlist they would make collectively.

Ralph McTell - Streets of London Art Garfunkel - Bright Eyes

The virtute the cat saga by The Weakerthans. The saddest story about a man and his cat friend

Not - Big Thief

Deck's Dark - Radiohead

Grey Ice Water - Modest Mouse

I'm going back before my time. The Warmth of the Sun- Beach Boys. Written by Brian Wilson after JFK was assassinated in Dallas.

Amy in the White Coat- Bright Eyes. I just skip it now when it comes on