I <3 Shel Silverstein.

I'm surprised by the amount of people who listed Radiohead songs as being depressing. I like Radiohead, but for the most part, I find a lot of their songs devoid of any real strong emotions. Someone listed The Weepies up above, their song 'Love doesn't last too long' I think is real depressing. I made a mix cd with a bunch of Weepies songs on it, a bunch of rather up beat ones, and then that depressing one at track five or so. This was summer of 2007, around the same time I first met and started spending a lot of time with the girl that I am currently dating, and I just remember so many instances where we'd be in my car, driving somewhere or something, all bright and cheery in the way that you are in the beginning of a relationship, and then that song would come on.

Anything by the Smiths, as well.

I always thought Take Me Out Tonight by The Smiths was one of the most subtle, multi faceted, almost "hidden" sad songs there ever was...

Def have to agree with this. Beck had gotten out of a long term relationship with a girlfriend, around when he started to record this album. You can REALLY sense it in this album. It is kinda crazy how feelings of sadness produce such good songs. If you are a Beck fan, check out Sea Change. Saddest song on the album, hard to say, but it would be wither Lost Cause, The Golden Age, or Already Dead. Hell just look at the cover, you can just see the sadness in Becks eyes. :o:

Neil Young has some pretty sad songs. I love Cortez The Killer.

Aussie songwriters = great sad song writers! Who could go past the melancholy pf the Whitlams Eternal Nightcap album, or the musing of Steve Kilbey of the Church... some of the Heartbreaking songs the Go Betweens have written... there's a treasure trove of sad music by these bands.... I beseech everyone to seek them out and listen!

No Bill Berry
 

'Up' was depressing for me because of the absence of Bill Berry. I think you can really tell the difference with that album.

That is a sad one. He passed away about a year later.
:(

Yeah, Up by REM can be a pretty depressing affair at times, musically and lyrically... but there are splashes of hope from moment to moment spread out through the album... Walk Unafraid always kinda lifts me up from when I feel embarassed and awkward, and there's a strength and beauty in lines like "someone has to take the fall/ why not me? If consequnce chose differently, if fate had played its hand/ my actions make me beautiful, dignify the flesh/ me, I am free...

I can dig it. Lotus is the heaviest and saddest track there, I think.

that song "when i was 17"...forgot who it was by.
but simpsons ripped it off...

I always "Four Seasons In One Day" by Crowded House to be a pretty darn sad song...

"Asleep"
 

Jeez, there are so many great songs to just sit and wallow with.

One that gets me every time is "Asleep" by the Smiths.

Hope nobody suggested that already.

At 17 I think was by Janice Ian initially.

Oh yeah, I remember that Song and the Simpsons knock off of it...

When I was seventeen, I drank a very good beer...

Morphine - Saddest Song
Great imagery my friend

sad
 

Andrew McCahon sucks, but Konstantine is really sad. Makes my eyes burn.

So,
Konstantine - Something Corporate
Sleeper 1972 - Manchester Orchestra
Jesus Christ - Brand New ("Jesus Christ I'm alone again, so what did you do
those three days you were dead? 'Cause this problem's
gonna last more than the weekend.")
Oh, Deceiver - Right Away, Great Captian
No Name No. 5 - Elliott Smith
Why I'm So Unhappy - Dntel
This Blackest Purse - Why?
A Ghost Beneath the Tower - The Winston Jazz Routine
My Sundown - Jimmy Eat World
Your Ex-Lover Is Dead - Stars
I've Been Eating For You - Bright Eyes

I approve of about half your list and your username just makes me laugh.

Nothingman by Pearl Jam... got it on right now and it nearly breaks my heart in two every time I hear it...

Said the whale - Curse of the currents/from autumn to ashes - chloroform perfume
Works every time :}

I can't believe a not single one of you mentioned Dead Of Winter by Eels. Easily the saddest song I've heard (about his mother, who he was nursing through her final days battling cancer when the song was written)

Also, nice one to whoever said This Woman's Work by Kate Bush.

She's Gone-Tindersticks.

Oh by the breeders is definetly a tear jerker

I always found the re - recorded version of "Here Comes the Flood" by Peter Gabriel to be really sad sounding... just him and a piano and some really saddening lyrics about a flood arresting a village's life... I also always used this song as a bit of a parallel to the times in my life I've felt overwhelmed and "flooded out"... but that's just my personal adaptation of it...

Tiny Vessels-Death Cab for Cutie
November-Azure Ray
I'm Your Puppet-Gregory and the Hawk

Martin Sexton - Where Did I Go Wrong With You

Cake - Long Line of Cars - I think it's about a dude that blows his head off in traffic.

Yellow - Coldplay

The original Needle of Death by Bert Jansch is easily one of the most depressing songs of all time. It is one of the only songs that have ever made me cry, in fact I can't even think of another. Eels also have a lot of very very sad stuff, it depends on what was going on in E's life when he was writing the music.

Yeah, the Eels definitely do have some incredibly sad songs in their catalogue... but E definitely had some deep dark stuff going on in his life at the time if I remember rightly... I am thinking songwriting must have been quite the cathartic experience for him in those times...

Amor for sleep- Car underwater.

Hideaway by Karen O & The Kids just flat-out puts tears in my eyes. Something about it just gives you a reminiscent feeling.

Angry Son by Indian Summer.

that too.

A lot of good ones already mentioned. A few I didn't see:

Sufjan - Casimir Pulaski Day

Atmosphere - That Night
"She was sixteen
Another young angel with clipped wings
She came to the shows, but I never met her
Don't even know if she was listening
That night, somebody lost a daughter
He raped and killed her at the venue
I can't comprehend what her friends must've been through
That night, the sun went dark
Now watch everyone on the tour bus fall apart
That night, Lord have mercy
That music died that night in Albuquerque"
^A song Slug 'wasn't supposed to write'

That's like, happy sad. God do I love that song. It's happy and warm sounding, but such a sad story.

I think the saddest Soofyan song is For The Widows In Paradise

I'm listening to Pulp's This Is Hardcore album right now... God I never realised how many sad songs there were on this... lotsa break up sounding stuff, forlorn lovers, unrequited feelings...the track I'm listening to now "TV Movie" is pretty darn sad...

I bet Hospice is a sad album, it's about caring for someone that's terminally ill and dying of cancer, I'm not going to be descriptive because I didn't care for it that much and got old fast but it's probably got very sad lyrics as well.

And yeah, if you listen to the lyrics on the songs on each of E's albums, you can definitely tell when his life is going good and when he's having a bad time. In some of those song he really pours his soul into his songwriting. Not Hombre Lobo though, that was ****.

betterman or wishlist by pearl jam.

I personally think Casimir Pulaski Day is much sadder than Widows. But don't get me wrong, both are such beautiful songs. I'm not sure if you'll get me, but they're different types of sad... if you know what I mean.

That song by Cat Power "Names" of her album Free. So sad.