I am making a CD of heartbreaking songs

Probably not very well known around here because it so mainstream country, and it was Leann Rimes, bt try listening to a song called "Probably Shouldn't Feel This Way" without having some kind of feeling. Very Sad
 
SHE'S ACTING SINGLE, I'M DRINKING DOUBLES
Gary Stewart


I've seen men look at before
And they think, I don't see them
I'd like to think it makes me proud
But, I'm only.. fooling me

I know she'll be lookin' back
The minute I'm not there
While she pours herself on some stranger
I pour myself a drink somewhere

She's acting single
I'm drinking double
I hide my pain
I drown my troubles

My heart is breaking
Like the tiny bubbles
She's acting single
I'm drinking doubles

I know all she plans to do
But I don't know where or when
If I ask who that stranger was
She'll just say, "an old friend"

I'm not weak, I tell myself
I stay because I'm strong
The truth is, I'm not man enough
To stop her from doing me wrong

She's acting single
I'm drinking doubles
I hide my pain
I drown my troubles

My heart is breaking
Like the tiny bubbles
She's acting single
I'm drinking doubles

She's acting single
I'm drinking doubles
I hide my pain
I drown my troubles
 
By Faron Young originally, and Willie Nelson has a great version:

Hello walls (hello hello) how things go for you today
Don't you miss her since she upped and walked away
And I'll bet you dread to spend another lonely night with me
But lonely walls I'll keep you company
Hello window (hello hello) well I see that you're still here
Aren't you lonely since our darling disappeared
Well look here is that a teardrop in the corner of your pane
Now don't you try to tell me that it's rain
She went away and left us all alone the way she planned
Yes we'll have to learn to get along without her if we can
Hello ceiling (hello hello) I'm gonna stare at you a while
You know I can't sleep so won't you bear with me awhile
We must all stick together or else I'll lose my mind
I've got a feeling she'll be gone a long long time (hello hello)

Speaking of Gordon Lightfoot, how about "The Wreck of the Edmund Fitzgerald?" Haunting song.

The winner, of course, is "He Stopped Loving Her Today."

Country music has hundreds of classics in this genre, try Webb Pierce's-

There stands the glass ...
That will ease all my pain ...
That will settle my brain ...
It's my first one to day ...
There stands the glass ...
That will hide all my tears ...
That will drown all my fears ...
Brother, I'm on my way. ... ...

CHORUS
I'm wond'ring where you are tonight
I'm wond'ring if you all right
I wonder if you think of me
In my mis-e-ry
There stands the glass
Fill it up to the brim
Till my troubles grow dim
It's my first one to day.
 
accuratehorn-- Willie Nelson techincally did the original Hello Walls since he wrote it. But, Faron Young made it famous.
wink.gif
(I love both versions)

I'll thrown in:

"New Yourk Hold Her Tight" - Restless Heart
"If Hollywood Don't Need You" - Don Williams
"Hello Darlin'" - Conway Twitty

And, "He Stopped Loving Her Today" is definitely #1 on any list like this. Sometimes I get choked up just thinking about that song.
 
Every time I click on this thread I think of more songs and can't leave without writing them down

A couple from Dan Seals

"Addicted"
"Everything That Glitters Is Not Gold"
 
Recovering the Satellites - Counting Crowes
(Hell the whole album)

Late for the Sky - Jackson Browne (Good Call, I still remember that scene from "Taxi Driver.")

Elton John -
Your Song
Sixty Years On
My Father's Gun
Talking Old Soldiers (Great Lyrics)
Levon
Mona Lisas and Madhatters
High Flying Bird
Hey, Hey Johnny - Empty Garden (About John Lennon)

Billy Joel -
She's Always a Woman
Captain Jack
Allentown
Goodnight Saigon

Jim Croce -
Tomorrow's Gonna Be a Brighter Day
New York's Not My Home
I Got a Name

Eleanor Rigby - Beatles
Only Women Bleed - Alice Cooper
Taxi - Harry Chapin
In My Life - Beatles
Spread Your Wings - Queen
Fire and Rain - James Taylor
In the Arms of an Angel - Sarah McLachlan
Drinkin' Thing - Gary Stewart

An for some reason, ever since I was a kid I thought "Beth" by Kiss was depressing...
 
I second SRV's "Life Without You." I dedicate it to my father every January 21st.

I would add U2's "Bad" to the list. Haunting music, haunting, voice, and haunting lyrics. Bono, by his own account, sings about the pain and confusion of a friend's heroin overdose.

Because its associated with the Christmas season, Dan Fogleberg's "Same Old Lange Syne" often gets overlooked. Not about a breakup, but the feelings and emotions that come washing over you years later when you, by chance, see that person your soul still quietly weeps for.
 
Rod Stewart -- Reason to Believe, Mandolin Wind. Just now listening to "Reason to Believe," so that's why.

But Todd Snider's "You Think You Know Somebody" is why I'm posting. Won't do a spoiler here, but it's a gut-wrencher about a childhood friend and that friend's child. For a guy who's a hoot, Snider knows how to bring you down, but if you've read much about him, you know why.

Robert Earl Keen's "Then Came Lo Mein" is a killer, too, about a breakdown. He's also got a bunch of other good depressing stuff.

Trout Fishing In America's family songs are usually a good remedy for any of the stuff on this thread.
 
Now that you mention Jim Croce, I think "Time in a Bottle" is extremely depressing, considering how he died shortly after that song came out.

Another vote for U2's "Bad." That is one of my favorite U2 songs, but I just don't listen to it often, if you know what I mean.
 
Janis Ian - Seventeen
REM - Everybody Hurts
Harry Chapin - Cats In The Cradle
Frank Sinatra or Ray Charles & Wille Nelson - When I Was Seventeen
Eric Clapton - Tears In Heaven
Sarah McLachlan - I Will Remember You
Elton John - Sorry Seems to be the Hardest Word
Elton John - Your Song
Don McLean - Vincent
Tori Amos - Silent All These Years
 
Didn't take the time to read and see if someone posted these, but Damien Rice's "Blower's Daughter," "Cheers Darling," and "Delicate."

All off the same album "O", all great, sad songs.
 
I have to just second a few that are already here.

All That Glitters Is Not Gold is heartbreaking, but also uplifting (at least to me) because you just get the sense that Dad + kiddo are gonna be ok, but would really rahter have the old life back. The one that wrecks me to this day is ...

Cats in the Cradle. I used to love listening to the song because the melody is really pretty, but then I realized that it wasn't a good thing that Son had grown up just like Dad, but a bad thing, a tragedy if you will. Given the closeness of my relationship with my dad, that day marked the downfall of that song for me. I still love it, and treat it as a constant reminder to not let it happen to me.

Oh, and He stopped Loving Her Today is tough, no doubt.
 
"June 18, 1976" by Pedro the Lion

A song written about the suicide of a young mother who jumps off the roof of a hospital after giving birth. Its wrist-slittingly sad.
 
The Beatles - Yesterday
James Taylor - Fire And Rain
Frank Sinatra - It Was A Very Good Year
The Temptations - I Wish It Would Rain
Sting - They Dance Alone (Cueca Solo)
Classics IV - Traces
Billy Paul - Me And Mrs. Jones
The Platters - Smoke Gets In Your Eyes
Peter, Paul, And Mary - Three Ravens
Benny Goodman - Goodbye
Fleetwood Mac - Oh Daddy
 
Sufjan Stevens - John Wayne Gacy Jr.

Manages to make Gacy a sympathetic character. Music and lyrics work perfectly there.

It's a quiet song, and it grabs you, and as the last tone of the piano fades at the end of the song, you can hear Sufjan sigh heavily. For some reason, that make the hair stand up on the back of my neck.
 
"The Drugs Don't Work"- Ben Harper

I've always thought "Senora's Death Row" was the saddest song ever, but it's associated with such a pleasant nostalgia for me that it doesn't really make me sad. It doesn't really seem fit to have REK on your suicide watch playlist anyway.
 
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