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.