a work of great sadness and joy is Tom Waits' 'Black Ryder' cd The Black Rider (1993 Studio Cast) [CAST RECORDING] Tom Waits, William Burroughs especially hearbreaking are cuts:

3. November
9. The Briar and the Rose
12. I'll Shoot the Moon
18. Lucky Day
19. The Last Rose of Summer

especially joyous is cut:
10. Russian Dance

I would vote for 'Luck Day' or 'November' as saddest