Thinking for today, most of my favourite tracks by Simon & Garfunkel, Jim Croce, Neil Young, as well as my favourite country by Kris Kristofferson, Gordon Lightfoot and Merle Haggard are those that strike me as the saddest music wise (I'm lazy to follow the lyrics though). This is one of them: And that striking melancholy vibe is just what makes country one of my favourite music .
Every new edition of this thread there remains always missing an essential artist or band, for that matter. 7 pages thus far, and this thread still couldn't be an exception either - why nothing by ABBA posted so far? Here goes my favourite: ABBA - The Winner Takes It All
Water Liars- "Wyoming" (The official video is also on YouTube, but I've got a feeling the listowner(s) wouldn't be too happy about someone posting it. It's a bit naughty.)
The last verse of Tom Waits's "A Little Rain," always gave me a sad chill. "She was fifteen years old And never seen the ocean, She climbed into a van with a vagabond, And the last thing she said was, 'I love you, Mom.' And a little rain never hurt no one..."
Here's another outstanding example (and with a magical arrangement too) - Ronnie Hawkins, Home from the Forest:
Concerning Popular Music, sometimes there is music that expresses the feelings and emotions pretty more than the sung words... to me at least: Vangelis / Heaven and Hell Part1 / Movement 3
Prine wrote some of the greatest sad songs ever. Hello in There is just the tip of the iceberg. Don't forget -- Six O'Clock News Souvenirs Speed of the Sound of Loneliness He Was in Heaven Before He Died The Hobo Song Summer's End
I can't believe it hasn't been mentioned yet, but the saddest song ever is The Wreck of The Edmund Fitzgerald.
"Patches" by Dickey Lee. Boy's parents won't let him see his girl because she lives in the bad part of town, girl thinks he doesn't come to see her because he doesn't love her any more, girl drowns herself, boy joins her. How much sadder can it get?
A soulful contribution to the "death of the childhood sweetheart" collection: The Chi-Lites - Toby (1974)