The Five Saddest Songs Ever Written

Categories: Music

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Feeling down and want that extra push into suicide land?

Here are your five best bets:


(5) "Hello, It's Me," by Todd Rundgren

The simple, conversational tone, along with dark feelings like, "Maybe I think too much, but something's wrong," make this 1968 classic achingly intimate. Its raw sweetness slays me every time.


(4) "Anyone Who Had a Heart," by Burt Bacharach/Hal David

A wail of a bad time and a mashochist's wet dream, this 1963 chart topper is also a great venue for a vocalist wanting to play victim and belt out some hurt. Number one with a hankie.


(3) "If Love Were All," by Noël Coward

The dark side of Britain's longtime court jester, this deceptively simple ballad is a plainly stated, deeply felt, and very wise plaint for true romance.

"I believe the more you love a man / The more you give your trust / The more you're bound to lose." Been there!


(2) "Smile," by Charlie Chaplin, John Turner, and Geoffrey Parsons

Intended as a cheer-up song to someone whose heart is loudly breaking, this classic always ends up making everyone feel worse. The melody is so sweet and brittle and the emotions so raw that the singer usually starts falling apart while singing, "Light up your face with gladness / Hide every trace of sadness ..." Killer shit.


And the winner...

(1) "Good Morning Heartache," sung by Billie Holiday

The ultimate depressed person's cry of submission, "Heartache" welcomed a mood spiral at a time before the right meds were on the market. Lines like, "You old gloomy sight / Thought we said goodbye last night," are bone-chilling in their resignation. By time Billie tells heartbreak to just "sit down," the razor's on the wrist, and I'm sort of loving it.

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91 comments
Heguardsyou
Heguardsyou

Aubrey by David Gates. Literally makes me weep...

Melinda9
Melinda9

Somewhere from West Side Story, especially as sung by Reri Grist from the original Bway cast - I always tear up when I hear it.A lot of Puccini arias also make my tears flow - Un Bel Di or Senza Mama or Ch'ella mi creda from La Fanciulla del West. And Ave Maria from Otello (Verdi).

Faith
Faith

I don't consider "Hello, It's Me" a sad song. A bittersweet song, yeah. But straight up SAD? Nah (but it is one of my favorite songs). And Luther Vandross' version of "Anyone Who Had a Heart" is masterfully heartbreaking.

My suggestions:"Seventeen" - Janis Ian (where's the Kleenex?)"My Man" (from "Funny Girl") - Sad, dramatic and defiant; Barbra's specialty."Volcano" - Damien Rice. The very first time I heard that song I cried like a baby (I had just gotten dumped). I have difficulty listening to that song even now...

Bostonspin
Bostonspin

"Mad World" by Tears for Fears -- In fact, almost any song from their album "The Hurting."(e.g. "Pale Shelter", "Watch Me Bleed", "Memories Fade", "Suffer the Children")

Gregeieio
Gregeieio

I Can't Make You Love Me by Bonnie Raitt

puck30
puck30

Just about any track from Supertramp's 'Famous Last Words' makes me want to jump off a bridge in slow motion.

Pat361
Pat361

"Mr. Lonely" sung by Bobby Vinton is the one of the most heartbreaking songs I have ever heard.

Snats
Snats

"Long, Long Time" -- Linda Ronstadt

bsomers
bsomers

Guess I'll Hang My Tears Out to DryLittle Girl BlueSend in the ClownsAnother Winter in a Summer TownAnyone Can Whistle

Melinda9
Melinda9

When Can I See You - Babyface

avonproud
avonproud

Starry Starry Night - Don McLeanAubrey Was Her Name - BreadWicked Game - Chris IsaakRainy Days And Mondays - CarpentersPachelbel Canon

FrankRay
FrankRay

Elliott Smith's "Miss Misery"

on a lighter note...
on a lighter note...

Those are all pretty sad songs but I wonder why no one mentiones Antony. "Hope there's someone" or "I fell in love with a dead Boy" will turn on the waterworks instantly...

Jeff Abraxas Porter
Jeff Abraxas Porter

Love will tear us apart: Joy DivisionYou cry out in your sleep,All my failings exposed.And there's a taste in my mouth,As desperation takes hold.

Bruce
Bruce

Also, "Diamonds and Rust"--Joan Baez."Now we're standing by the window in that crummy hotel over Washington Square/Speaking strictly for me we both could have died then and there."

Rivoli
Rivoli

I Only Wanna Laugh-from the flop 1969 musical JIMMY

Rivoli
Rivoli

My Buddy-Streisand versionIt Must Be Him-Vikki Carr

Helene
Helene

Nowhere Man/Drinking Again/Lush Life/Black Coffee/At Seventeen/Poetry Man/One for my baby/She's Got You/Eleanor Rigby...."...we're drinking my friend, to the end of a brief episode..."

Siouxie
Siouxie

Syd Barrett anyone?  He surely penned some of the most melancholic songs ever.  Dominoes is the first that comes to mind.

F. Packer
F. Packer

PEOPLE!!! "Seasons in the Sun"?? I'm still in therapy!

Jdun
Jdun

"Wreck on the Highway" Bruce Springsteen  from The River

Watsmata4u
Watsmata4u

"I'm So Lonesome I Could Cry" by Hank Williams

Bionic_idiot
Bionic_idiot

"The Drugs Won't Work," by The Verve. Hate the band, LOVE that sad sad song.

Atlanta Dan
Atlanta Dan

Fantastic heartbreaking selections all. Hell, I'm tearing up just reading them.  Might I add:"If You See Her Say Hello" Bob Dylan"Alone Again (Naturally)" Gilbert O Sullivan"Wild Horses" The Sundays cover version"Goodbye to Love" Carpenters"Green Green Grass of Home" Tom Jones (?)

AntiBoyHell
AntiBoyHell

I bought 'Good Morning Heartache' and 2 other Billie Holiday tunes 4 weeks ago.  Just fucking amazing art.  I love having a good cry to 'Good Morning Heartache',  I live in Harlem and when I hear it I feel like Billie is in the room with me!  I know where those blues are coming from and it's as relevant today as it was then.

Dee Snyder
Dee Snyder

Hello?!? Anyone ever heard of Leonard Cohen here?

"Yesterday's Man." Look up the lyrics. That is all.

dre
dre

Jermaine Jackson singing Smile at Michael's funeral was pretty heartbreaking- I don't know how he got through that song.Also almost any version of Hallelujah- but the one especially by John Cale.

Ramadu
Ramadu

'How Do You Keep The Music Playing' by Alan & Marilyn Bergman.

Fflintstone
Fflintstone

Blue Valentine or Letter from a Hooker In Minneapolis, Tom Waits.

Sastout
Sastout

Pissing in the River By Patti Smith

Cokane1
Cokane1

Hurt by Timi Yuro - No argument. And This Womans Work by Kate Bush

Gay Movie Fan
Gay Movie Fan

Down So Low by Tracy Nelson (look it/her up on Youtube). 

lameatman
lameatman

'Not A Day Goes By' Sondheim. Bernadette Peters" I'll die day,after day, after day, after day,after day, after day,after day"

Also ' Gone to Soon' ,sung by Michael Jackson, for Ryan White

Kornish
Kornish

"Society's Child" and "At 17" by Janis Ian

"Desiree" by Laura Nyro

"Eleanor Rigby"

Agree about Diana's "You've Changed"

Ilene
Ilene

"He Ain't Heavy, He's My Brother"

"Superstar"  by the Carpenters

"Patches"

nostradavid
nostradavid

"Seeds and Stems (Again)" from Lost In the Ozone by Commander Cody and His Lost Planet Airmen

Boopsie Schwartz
Boopsie Schwartz

Agree on the Judy classics, esp. Merry Little Christmas.  I also always get weepy when I hear The Circle Game by Joni Mitchell.

Melinda9
Melinda9

My sad contributions: 1) Walk On By - Dionne Warwick 2) My Life - Jj 3) The Way Love Used to Be - The Kinks 4) Stolen Moments - Oliver Nelson (sad tune) 5) Hold On Hold On - Neko Case.

Monsieurpatric
Monsieurpatric

Michael choux, Consider J. Joplin's final piece "Pearl" as a whole and take in what a loss was had.  Elements of Piaf, serious interpretive jazz, colorations....

BinI
BinI

"Hello in There"--as sung by Bette Midler or John Prine or anyone.

"You know old trees just grow stronger and old rivers grow wilder every day...but old people just grow lonesome...waiting for someone to say, 'Hello in there....Hello'."  Sob!

Tozere
Tozere

He stopped loving her today

Dangerwillrobinson
Dangerwillrobinson

Stevie Wonder's "Super Woman (Where Were You When I Needed You?)".

MadTown56
MadTown56

Absolutely.  What heartbreak.

Atlanta Dan
Atlanta Dan

Oh, and one I forgot to add..."Hold On" Sarah McLachlan

puck30
puck30

Hooker is great, let me add 'On The Nickel'.

Ramadu
Ramadu

'Not A Day Goes By' Sondheim. Bernadette Peters

This song, a bottle of pills and a fifth of vodka and you're ready for the the Big Sleep!

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