“Cat’s in the Cradle”
“Empty Chairs” by Don Maclean. Thread question answered.
"Tears in Heaven’ by Eric Clapton, especially knowing what it is about.
Strange Fruit. Billie Holiday.
“Into the West,” sung by Annie Lennox on the final credits to Return of the King.
I know plenty of sad songs, have sung some myself but this is the latest uber-sad song I’ve heard.
Pray For Newtown - Sun Kil Moon
The whole album, called Benji, is sad, painful even, in its rawness, bittersweetness. I recommend it.
Skates by Hayden. Song about working in a department store, helping a man purchase some ice skates. Turns out the guy wanted ice skates so he can go rescue his drowned wife from the river when it freezes over, since he can’t swim.
That’s my classic go-to saddest song, but I heard Band of Horses’ No One’s Gonna Love You (“more than I do”) a few years ago and it crushes me every time I hear it. But for personal reasons…it’s not actually that sad.
Casimir Pulaski Day by Sufjan Stevens. The lyrics start with “Goldenrod and the 4-H stone/The things I brought you when I found out/You had cancer of the bone” and it goes from there. The rather upbeat melody just makes it all sadder.
Yeah. And around that general time period, there was a whole spate of “dead teenager” songs. See “Laurie (Strange Things Happen),” “Patches,” “Teen Angel,” “Dead Man’s Curve,” “Tell Laura I Love Her,” etc.
ETA: The wonderful Steve Goodman hits three of these songs here, after starting out with “Born To Be Wild.” (Start at about 3:00 if you want to skip the “Born to Be Wild” part.)
“Dust Bowl” by 10,000 Maniacs.
I used to think “Windsurfer” (guy falls in love with somebody he never has a chance with) from the same album was sad when the same thing happening to me was fresher in my memory, but after almost 18 year of marital bliss it doesn’t have the same effect on me. “Tears in Heaven” might be close for me now; I lost a grandparent around the time it came out.
Beat me to it.
"Without You’ by Badfinger as recorded by Harry Nilsson in 1971:
“The Last Time I Saw Her Face” by Gordon Lightfoot. Can’t even get by the first verse before tears well up. Gordon Lightfoot - The Last Time I Saw Her Face - YouTube
“The Kids” by Lou Reed ( from the album Berlin ). Should depress even the most psychotically cheerful person ;).
Oh, where to start…
Early Mornin’ Rain (link is to PP&M’s cover)
Probably the saddest of the bunch, though, is Jackson Browne’sIn The Shape of a Heart
The video’s a little goofy, but Buck Dharma’s Your Loving Heart is pretty sad.
I always thought The Ballad of Ira Hayes was up the list.
The Great Dust Storm Disaster is as sad as it gets, but probably too hokey/old-timey for a lot of people.
I was getting choked up over Cortez the Killer the other day, but I wonder who else will wait that long for it or see it that way. It is supposed to be about Cortez, but spends almost the entire song mythologizing the Natives, on and on, until the last line says apparently all there is to say about Cortez: what a killer. The Native Apocalypse is basically left to your imagination. What can I say? Dead Indians make me sad.
Mentioned already but Eric Bogle’s version of “The Band Played Waltzing Matilda” is a downer.
If you like horses The Last Parade (a sung version of a Banjo Patterson poem) should do the trick as well.
The Best Ever Death Metal Band In Denton by the Mountain Goats is another contender in my opinion.