A snickering cherub that showed graphic slaughterhouse scenes for the first 15 minutes of the concert I attended a couple of years ago. Love the Smiths and earlier Morrissey songs and I will always appreciate that but there’s no doubt in my mind that he’s a miserable bastard.
Nah, he’s hilarious. Keats and Yeats may be on our sides, but Wilde really is on his.
Hey, that’s…comedy gold…right? 
Patsy Cline! Every song of hers is so sad, and her voice is so haunting.
Yeah… between that and the dumb couple salsa dancing to his music in front of me, it was a real joke.
To be fair, I’ve never bought in to that part of his act and being a straight female omnivore, I’m not his target audience.
Gillian Welch. But I could still hear her for hours on end, so I guess it’s a sort of elated depression, whatever that means.
For me it’s “Hello.”
Also Tori Amos, especially “Winter.”
Love the song, but it depresses the hell out of me.
And pretty much Assebmage 23’s entire catalog.
Ugh, that should have been “Assemblage.” My cat is sleeping on one arm and I didn’t want to wake her. :smack:
I’m a little surprised to be the first to mention Gordon Lighfoot. When your greatest hit is 6 and half minutes on the sinking with all hands of a Great Lakes ore freighter, that’s some impressive sadness, right there.
Tom Waits - mainly the ‘pre-Bauhaus’ era.
His song characters are so wonderfully broken that you really root for their
redemption or success . . . and then he kicks you in the heart.
Tom Traubert’s Blues - - YouTube
Ruby’s Arms - Tom Waits - Ruby's Arms - YouTube
+1
“Grapefruit Moon” too…
For me, more than most, it’s Richard Manuel (as I’ve mentioned in other posts).
Plus one
Yep… Zombie drivel
and the overrated jackoff’s of Oasis.
Luther Vandross, ‘Dance With My Father’. This song came out not too long after my dad died at the end of 2002. I heard the song for the first time while driving, and had to pull over and bawl my eyes out because I was afraid I would lose control of the car. My wife quite frankly couldn’t believe I could get that emotional over a song.
It took quite some time, but I finally got over it. I could listen to the song and appreciate it, and then Luther died. Now I can’t listen to his music at all, and he has (had) such an amazing voice.
The Rolling Stones: Songlyrics and music seem to ask for temporary asylum.
Queen: Too many words creeping across the music. A strong feeling of sadness, fear, and loss of hope last far longer than those reckless operas.
Not a singer, but a band: Pink Floyd. With the exception of their song, “Money”, I just can’t listen to Floyd. Everything I’ve heard from them other than “Money” just depresses me.
Dory Previn. In my yewth, there was nothing more uplifting to my tortured, adolescent soul than to listen to someone who was even more miserable than me.
Jane Olivor is a great singer, but wow - make sure there are no bottles of prescription drugs or razor blades in the house when you try to listen to one of her albums.
Bread - Everything I Own. It’s sad in the first place, and then I found out the dude’s singing about his deceased father. 