I am making a CD of heartbreaking songs

When I saw the thread title, the sappiest song I've ever heard (and yet, it still chokes me up)...

"I'll Be True to You" -- Oak Ridge Boys.


Also, Bruce Robison's "Angry All the Time" hits too close to home sometimes.

And for some reason, although I like the song, "100 Years to Live" by Five For Fighting depresses me.
 
Springsteen has some great ones. Stolen Car, mentioned already was first that came to mind. But also:

Most of the Tunnel of Love album, especially "One Step Up" for me
Meeting Across the River
Point Blank
Nebraska
Untitled song at the end of the new Magic album, "When they built you, brother, they broke the mold"
 
One to consider:

Old Blue Lyrics:
I had an old dog, and his name was blue
Bet your life he was a good dog too
Blue chased a possum up a hollow limb
Possum won, got the best of him
Bye-bye blue
You good dog, you
Bye-bye blue
You good dog, you
Blue he died, and he died so hard
He shook the ground in my backyard
We lowered him down with a golden chain
Every link we’d call his name
Bye-bye blue
You good dog, you
Bye-bye blue
You good dog, you
My old blue was a good old hound
You could hear him holler for miles around
When I get to heaven, first thing I’ll do
I’ll grab my horn and call old blue
Bye-bye blue
You good dog, you
Bye-bye blue
You good dog, you
Bye-bye blue
You good dog, you
Bye-bye blue
You good dog, you
Bye-bye blue

And if you can get past the maudlin nature of these two:
D-I-V-O-R-C-E and I Don't Want to Play House.
 
I did a keyword search on this entire thread and didn't see one mention of "Richest One" by Toni Price. That's just a shame. A damn shame.

On an Austin, Texas message board no less.....
 
This is all Texas Country (my music of choice) so if you don't like Texas Country then ignore this post

Jack Ingram - She Don't Love You
Jack Ingram - Maybe She'll Get Lonely
Roger Creager - Crying, Moaning
Aaron Watson - What She Don't Know
Cory Morrow - Love Me Like You Use To Do
Chris Knight - Cry Lonely (now covered by Ragweed)
 
I swear to God this song actually makes me cry sometimes:


The Blind Man in the Bleachers - - Kenny Starr






He's just the blind man in the bleachers to the local hometown fans
And he sits beneath the speakers way back in the stands
And he listens to the play by play, he's just waiting for one name
He wants to hear his son get in the game

But the boy's just not a hero, he's strictly second team
Though he runs each night for touchdowns in his fathers sweetest dreams
He's gonna be a star someday though you might never tell
But the blind man in the bleachers knows he will


And the last game of the season is a Friday night at home
And no one knows the reason but the blind man didn't come
And his boy looks kinda nervous,sometimes turns around and stares
Just as though he sees the old man sitting there


Well, the local boys are tryin' but they slowly lose their will
Another players down and now he's carried from the field
At halftime in the locker room the kid goes off alone
And no one sees him talkin' on the phone

And the games already started when he gets back to the team
And half the crowd can hear his coach yell, "Where the hell you been?"
"Just getting' ready for the second half", is all he'll say
"Cause no you're gonna let me in to play"

And without another word he turns and runs into the game
And though the silence on the field, loudspeakers call his name
It'll make the local papers how the team came from behind
When they saw him playing out his heart to win

And when the game was over the coach asked him to tell
What was it he was thinkin' of that made him play so well
"Well, you knew my Dad was blind", he said, "Tonight he passed away"
"It's the first time that my father's seen me play"
 
Didn't read the whole thread but I'll add "Houses on the Hill" by Whiskeytown

Eisenhower sent him to war
He kept her picture in his pocket that was closest to his heart
And when he hit shore
Must've been a target for the gunman.
 
I'm back, and I'm beginning to think I listen to this kind of music way too much also... A couple of these might be repeats from my other posts, I'm just going through some of the songs on my computer.

Jimmy LaFave - How It Must Remain
The Platters - Smoke Gets In Your Eyes
Kansas - Dust In The Wind
Glen Campbell - By The Time I Get To Phoenix
Glen Campbell - Everyday Housewife
Frank Sinatra - One For My Baby, One More For The Road
Hank Williams - I'm So Lonesome I Could Cry
Indigo Girls - I Don't Wanna Talk About It
k.d. lang - Constant Craving
Elvis Costello - Veronica
Emerson, Lake & Palmer - C'est La Vie
TLC - Waterfalls
Them - It's All Over Now Baby Blue
The Who - The Song Is Over
The Moody Blues - You Can Never Go Home
The Moody Blues - And The Tide Rushes In
Willie Nelson - Blue Eyes Crying In The Rain
Willie Nelson - The Great Divide
 
I can't believe no one has mentioned these:

Counting Crows - Raining in Baltimore

Dixie Chicks - Traveling Soldier


Both of those songs really hit me
 
I was just about to ask how Traveling Soldier went 6 pages without mention until I saw your post. Also not sure how this one didn't make it:

It makes no difference where I turn
I can't get over you and the flame still burns
It makes no difference, night or day
The shadow never seems to fade away

And the sun don't shine any more
And the rains fall down on my door

Now there's no love as true as the love that dies untold
But the clouds never hung so low before

It makes no difference how far I go
Like a scar the hurt will always show
It makes no difference who else I meet
They're just a face in the crowd on a dead-end street

And the sun don't shine any more
And the rains fall down on my door

These old love letters that I just can't keep
It's just like the gambler says: "Read 'em and weep"
And the dawn don't rescue me no more

Without your love I am nothing at all
Like an empty hall, it's a lonely fall
Since you've gone it's a losing battle
Stampedin' cattle, they rattle the walls

And the sun don't shine any more
And the rains fall down on my door

Well I love you so much that it's all I can do just to keep myself from telling you
And I've never felt so alone before

"It Makes No Difference" - The Band
 
Everclear - Pale Green Stars
Pete Droge - Northern Bound Train
Pete Droge - Fourth of July
Freedy Johnston - This Perfect World
Freedy Johnston - Bad Reputation
 
Ghost in this house - Allison Krauss also done by Shenandoah before Allison Kraus
Is It Raining at Your house by Vern Gosdin
Grey Eyes You know-Waylon
 
A few others:

"How Will I Ever Be Simple Again" - Richard Thompson
"Goodbye" - Steve Earle
"Jennifer Johnson & Me" - Robert Earl Keen
"Misfits" - The Kinks
"Tecumseh Valley" - Townes Van Zant
"Our Town" - Iris Dement
"Carmelita" - Warren Zevon
"Across the Border" - Bruce Springsteen
 
Damn, this is a long thread. I've always wondered if anybody actually reads these threads or just post their own suggestion. I'm certainly not about to read the 1000 or so suggestions on here.
 
Two Steve Goodman songs:

Penny Evans - sang a capella and personalizes the effect of war on the homefront.

A Dying Cub Fan's Last Request - a song before he died of cancer.
 
I was on the outskirts of a little southern town
Tryin' to reach my destination
Before the sun went down
The old CB was blarin' away on channel 1-9
When there came
A little boy's voice on the radio line
And he said
Breaker 1-9
Is anyone there
Come on back truckers
And talk to Teddy Bear


Well I keyed the mike and said
You got it
Teddy Bear
And a little boy's voice came back on the air
Preciate the break
Who we got on that end
I told him my handle
And then he began
Now I'm not supposed to bother you fellows out there
Mom says you're busy
And for me to stay off the air
But you see
I get lonely and it helps to talk
'Cause that's about all I can do
I'm crippled
And I can't walk
I came back and told him to fire up that mike
And I'd talk to him
As long as he liked
This was my dad's radio
The little boy said
But I guess it's mine and mom's now
'Cause my daddy's dead
Dad had a wreck about a month ago
He was trying to get home in a blindin' snow
Mom has to work now
To make ends meet
And I'm not much help
With my two crippled feet
She says not to worry
That we'll make it alright
But I hear her crying
Sometimes late at night
You know there's one thing
I want more than anything else to see
Aw, I know you guys are too busy to bother with me
But you see
My dad used to take me for rides
When he was home
But.... I guess that's all over now
Since my daddy's gone
Not one breaker came on the old CB
As that little crippled boy
Talked with me
I tried hard to swallow
A lump
That just wouldn't stay down
As I thought about my boy
Back in Greenville Town
Dad was going to take mom and me with him
Later on this year
Why l remember him saying
Someday this old truck will be yours Teddy Bear
But I know I'll never get to ride an 18-wheeler again
But this old base will keep me in touch
With all my trucker friends
Teddy Bear's gonna back on out now
And leave you alone
'Cause it's about time for
Mom to come home


But you give me a shout when you're passin' through
And I'll sure be happy to come back to you
Well I came back and I said
Uh...Before you go 10-10
What's your home 20
Little CB friend
Well he gave me his address
And I didn't once hesitate
'Cause this hot load of freight
Was just gonna have to wait
I turned that truck around on a dime
And headed straight for Jackson Street, 229
And as I rounded the corner
Oh I got one heck of a shock
l8 wheelers were lined up for three city blocks
Why I guess every driver for miles around
Had caught Teddy Bear's call
And that little crippled boy was having a ball
For as fast as one driver would carry him in
Another would carry him to his truck
And take off again
Well you better believe
I took my turn at riding Teddy Bear
And then I carried him back in
And put him down in his chair
And buddy if I never live to see happiness again
I want you to know
I saw it that day
In the face of that little man
We took up a collection for him
Before his mama got home
And each driver said goodbye
And then they all were gone
He shook my hand with a mile-long grin
And said
So long trucker
I'll catch ya again


Well I hit the Interstate
With tears in my eyes
I turned on the radio
And I got another surprise
Breaker 1-9
Came a voice on the air
Just one word of thanks
From Mama Teddy Bear
We wish each and every one
A special prayer for you
Cause, You just made my little boy's
Dream come true
I'll sign off now
Before I start to cry
May God ride with ya
10-4
And goodbye
 
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