What's the saddest song on your playlist?

If you ever see my driving down the street with tears streaming down my face and into my gray beard, it’s because this damn song came up in my playlist again:

“The Night I Learned How Not to Pray,” Iris Dement

If you don’t have a song that literally makes you cry like a baby ever time, which one at least makes your eyes a little misty?

Roy Orbison’s “In The Real World.” It’s a sad song as it is (being Roy, and all), but due to its personal relevance to me, it makes me cry every time I hear it.

I think the Dement song kills me because of the double tragedy: first, the family loses her baby brother, which breaks my heart as a parent. Then, instead of finding comfort in God, the tragedy understandably drives her away from God, which breaks my heart for her. Plus Iris just has that perfect, unique voice of hers that makes every song poignant.

That was the night I learned how not to pray
Because God does what God wants to anyway

White Winos by Loudon Wainwright.

Daddy Needs a Drink by Drive-By Truckers. It exudes hopelessness, and I think most people can see themselves in it at certain points of life.

Without You (Harry Nillson version specifically). The two people that wrote it both committed suicide, and I think Nillson really captured the emotions they put into it.

Angels by Robbie Williams - “And when love is dead, I’m loving angels instead”

I guess “Over You” by Paul Revere and the Raiders qualifies as sad, at least initially:

*"There’s a-gonna be some slow, slow walkin’
There’s gonna be some sad sad talkin’
There’s gonna be some flower bringin’
There’s gonna be some sad sad singin’
Over you, child, wo, I said over you
Hey, hey, oh baby, if I ever hear you say we’re through…

Oh, there’ll be a hole about 6 feet deep
For you, baby, to take your sleep
Into a coffin and a-down you go
And you will stay there, sleet or snow…

Wo, gonna kill you, baby
Tell me what I’ll do, what I’ll do
Oh baby, if I ever hear you say we’re through, wow*

:eek:

I’ve got a couple.

“What Do I Do With My Heart?” by the Eagles. The late Glenn Frey’s voice has never been on better display than in this song. It reminds me that we have lost not only a great tunesmith, but also a helluva singer.

“Never Without You” by Ringo Starr. A tribute to his fellow Beatle, the late George Harrison.

*And your song will play on without you
And this world won’t forget about you
Every part of you was in your song
Now we will carry on… Never Without you
Within you without you
Here comes the song it’s about you

I know all things must pass*

when the angels sing by social distortion

its the ultimate funeral song …

Without delving into all of my music…

“Guenevere” from the musical Camelot:

In that dawn, in that gloom
More than love met its doom
In the dying candle’s gleam
Came the sundown of a dream
Guenevere, Guenevere
In that dim, mournful year
Saw the men she held most dear
Go to war for Guenevere

Main and Broadway, a bitterly wistful breakup song by a Canadian trio called Cub.

Love letters, broken lockets,
Dead flowers, candy boxes,
That’s what you’re left with when it’s over

Coil–“Heartworms.”

The singer, Jon Balance, died after falling from a balcony while drunk.

Ronnie Drew’s rendition of “The Band Played Waltzing Mathilda”

My Immortal, by Evanescence

You used to captivate me by your resonating light
Now, I’m bound by the life you left behind
Your face it haunts my once pleasant dreams
Your voice it chased away all the sanity in me
These wounds won’t seem to heal, this pain is just too real
There’s just too much that time cannot erase

Break My Heart Sweetly, by John Moreland

*There’s a scar on my soul, so let me down easy
Break my heart sweetly, like you always do
I guess I can’t let go til you wreck me completely
Break my heart sweetly, drape me in blue *

Waiting on June

Johnny Cash’s Hurt cover.

I generally have to be watching the video as well, but it does get me choked up.

How Can I Help You Say Goodbye breaks me up now that my mom is dead.

Also, Gulf Coast Highway because I heard it a lot right after she died.

And when she dies she says she’ll catch some blackbird’s wing
Then she will fly away to Heaven come some sweet blue bonnet spring

My Hand To God by Daniel Amos

In this, the closing track of a concept album about a fictional couple named Bud and Irma Ackendorf, Bud is on his deathbed saying his last goodbye to his beloved wife.

Springsteen - Stolen Car.

(Runners-up include Joni Mitchell - River, Jackson Browne - Before the Deluge, Dire Straits - Romeo and Juliet, Queen - Save Me, Pink Floyd - The Gunner’s Dream.)