The rather lovely book This will end in tears: The miserablist guide to music has given me a playlist of melancholy songs I don’t know.
Marie by Townes van Zandt
Disintegration loops by William Basinski:
the iron oxide particles were gradually turning to dust and dropping into the tape machine, leaving bare plastic spots on the tape, and silence in the corresponding sections of the new recording …
Holocaust by Big Star
Past, present, and future by The Shangri-Las
Lush life by Billy Strayhorn
Dress rehearsal rag by Leonard Cohen
Highway patrolman by Bruce Springsteen
The Electrician by The Walker Brothers