1969, Written by a man who went on to take his own life. This and a few other songs are regarded as his "suicide notes".
I'm sure somebody has mentioned this one upthread, but it's tough to top (or bottom) Floyd's Wish You Were Here in my opinion. It's a simple song with a simple message that needs no elaboration. Two short verses and one "chorus," though I suppose it's more like a third verse since it's never repeated. And there's no explanation as to what Roger Waters is singing about, nor is any needed (though we know it's about their erstwhile guitarist, Syd Barret). And it's a sneaky song filled with misdirection. It follows a major tonality (C, G, D with a little A minor pivot) so it doesn't necessarily sound as if it will be sad, but it climaxes in heartbreak, albeit with Waters matter-of-fact way of delivering a message without a lot of pomp or sappiness. I mean, it's not like he's asking for too much. He just wishes you were here, no matter what that might entail. On a related note, I would also throw Floyd's High Hopes in there too, if only because it's the last song on the last Pink Floyd album and serves as almost a career retrospective for one of the most influential bands of all time. I don't have much use for the post-Roger Waters albums (honestly I think David Gilmour is a piss-poor lyricist (which he always knew) and only a competent singer), but this one still gets me every time:
For me it's always a tie between these two: First up, Billie Holiday "I'm a Fool to Want You." The song itself is sad, but at this point in her career, Billie Holiday was wracked by heroin, which gave her voice a cragginess that made her delivery of the lyrics even sadder. There are prettier versions of this song (Linda Ronstadt, Peggy Lee), but to me, Billie's version gets to the heart of longing for someone. They cheated on you, but your heart hasn't let go yet. Next, Elton John "Sorry Seems to Be the Hardest Word." About the end of a relationship, the lyrics ask all those questions that torment you when you're facing the end of a relationship, when you haven't quite accepted it because it wasn't your idea to end it. The funereal quality to the music make this, in my opinion, a song of mourning. As an aside, this is also the song I play before writing scenes that deal with my FMC's background as an abused teenager, because they fit that situation as well.
This was my mourning John - had me sobbing over taps - 'Life isn't everything...life isn't everything...sob...sob...' I found it one Sunday morning - there's an eccentric BBC guy Marc Tulley presents a 'spiritual' radio programme - just by coincidence the topic was death & attitudes to death, I was on the ropes, 'Death is but a journey along mystic highways unforshadowed by any meaning or comprehension. As the mystic yogi tells us...' then they played EJ at the end. My poor Dad had Enya played at his funeral and I'll never forgive that horror, bloody Orinoco Snow, foxake!
Shelter- Porter Robinson. To be fair... when I first heard the song, I wasnt moved. I thought it was an awesome song..... but then my sister showed me the video to it. now I cant listen to the song without feeling sad
Honestly, I think this song... The lyrics are so sad and the singer did a good job sounding emotional.
