Melancholic, depressive, miserablist, misanthropist singer songwriters

I guess that several of those adjectives certainly apply to Eliott Smith.  Died at age 34, suffered from alcoholism, drug use and depression, and wrote and performed some really great music.

I highly recommend "Figure 8" as one of his more "pop oriented" albums.  "Either/Or" as well is just fabulous.  But really I like his entire catalog. 

I find Leonard Cohen quite humorous and uplifting...G

Janis Ian has her moments, just to show it isn't a strictly male preserve.

steve

I know everybody thinks immediately of Leonard, but I also don't find his work depressing.

Mark Eitzel on the other hand ...... sublime and beautiful, but grim at times.

Richard Thompson , has his moments too, mainly when writing about his ex.

Mark E Smith.

Jono

Surprised no one has mentioned the Belfast Cowboy aka Mr Van Morrison.

Graham.

That bloke from everybody hurts-please shoot me-what's his face-something stype.

Melanie (had her moments) ...however her singing was so engaging and the arrangements outstanding  .. I never felt depressed .. I know it's hard looking up the sun when you know in your heart you will never be warm .. But there"s a show on babe rainbow and you, you got to go on. 

Her songs are full of great lines and it was hardly fair that she was third on the bill of a second rate show

but she did sing a song about her friend who did away with herself to the tune of a rocking band

in the end she cheered up and sung you gotta stop me from killing myself

but the saddest thing is her catalogue has been neglected 

There's nothing at the end of the rainbow, there's nothing to grow up for  anymore 

JS Bach could manage to deal with tragedy in a most uplifting way:

http://www.youtube.com/watch?v=2i5O923PzeQ

The Actus Tragicus ...

ATB from George

Billie Joe Armstrong of Green Day often chooses depressing topics for his songs, but the overall melody and drive of  the songs is usually very energetic.  Somehow that makes it possible to listen to an album full of lyrics about social decay and drug use, and feel invigorated.  Maybe it's the relief of angst.  He definitely has a gift for writing melodies.  Hopefully he can get himself rehabbed and back on a successful track.

John Martyn

Miserable, curmudgeonly old scroat though he is as a person, I've never found Van the Man's music at all depressing. Richard Thompson's stuff is pretty doomy though, which contrasts strongly with his personality.

Although a group rather than singer/songwriter, Porcupine Tree are pretty bloody depressing. Steven Wilson I guess.

Graham

I know an absolutely disgusting story about Van Morrison. When we meet up with Steve I will tell all

Roger Waters

From about 1974 to 1990: miserable, angry, bitter, misanthropic, gloomy... he's more cheerful these days, and not half as much fun.

Oh, you tease!

With rather splendid self-deprecating wit, Richard Thompson released the unofficial, fan-club only 'Doom and Gloom from the Tomb'.

The master of the 'love gone wrong' song. You gotta love him.

John.

I'd go for Antimatter. Currently a project of Mick Moss, but earlier Duncan Patterson was involved. 

Country & Western - someone even did a study.

"You can't imagine how it hurts me

To have you treat me like you do

Knowing that my love is just a joke to you

But I'll take it just to see you and laugh as teardrops fall

So when you need a laugh, give me a call

Everybody says I'm crazy to let you treat me this way

But I can't explain, so what else can I say

At least I'm on your mind when you're laughin'

Somehow that breaks the fall

So when you need a laugh, give me a call
I'd gladly trade the laugh you get for making fun of me

To be around the one I love and need so desperately

So even if the laugh's on me, I don't mind at all

So when you need a laugh, give me a call

So when you need a laugh, give me a call"

Peter Hammill's solo stuff, not that the Van Der Graaf material was that cheerful.

Roy Harper has his moments.

Tom Mcrae,

I agree Country & Western music can sound pretty damned depressing.

Do you know what happens when you play a C&W record backward?

....you get your wife back.... your pick up truck starts running.... your dog comes back to life... you find a job.....

but I'm sure it still sounds depressing.

And there you go! I think John Martyn is life affirming!

Tony McPhee fits the bill, with Groundhogs Solid being his finest example. Snowstorm, Jokers Grave and Corn Cob seriously are depressing/miserable. Strangely Solid is my favorite Groundhogs album, not a happy or bad track on it.

I completely agree!  It wasn't a criticism.  G