I just got a new pair of cheap headphones and noticed that songs that appealed to me most emotionally really sang with these phones, so I've looked up my 30, in no particular order. Not saying they're they're the greatest in some pseudo-objective sense. Just the songs that moved and still move me.
Hatfield and the North, "It Didn't Matter Anyway"
Camel, "Unevensong"
The Unthanks, "Starless"
John Cale, "John Milton"
Barclay James Harvest, "Galadriel"
King Crimson, "Islands"
Bonzo Dog Band, "Readymades"
Caravan, "Nine Feet Underground"
Gene Clark, "Some Misunderstanding"
Velvet Underground, "I'm Set Free"
Jonathan Richman and the Modern Lovers, "Morning of Our Lives"
David Ackles, "Be My Friend"
Kevin Ayers and the Whole World, "Red Green and You Blue"
John Coltrane, "Dear Lord"
Kinks, "Where Did My Spring Go?"
Paul Bley, "Mr. Joy" (either the piano or the synthesizer version)
Chico Buarque, "Mulher"
Circus Maximus (Jerry Jeff Walker) "Hansel and Gretel"
Aroah, "El Dia Despues"
Lou Reed, "Coney Island Baby"
Clarice Falcao, "Fred Astaire" (the Portuguese version is a little more entertaining than the English one, but both are so damn good who cares)
Hello Saferide, "Leaving You Behind"
El Perro del Mar, "How Did We Forget"
Laleh, "Goliat"
John Fahey, "Sligo River Blues"
Wintergatan, Paradis
Wayne Raney, "Gathering in the Sky"
Mono and World's End Girlfriend, "Palmless Prayer / Mass Murder Refrain"
Matching Mole, "O Caroline"
Loney Dear, "What Have I Become" ("and if I only knew why I was drawn to this"--kind of sums up the whole list)