We've all spent time with hundreds of sad songs throughout our listening lives and in researching my new book, This Will End In Tears: The Miserabilist Guide to Music [It Books, $16.99], I found that people tend to be aggressive in defense of the heart-wrenching power of their favorites melancholic tunes.
My book ends with a list of the top 100 saddest songs, which stands as a culmination of the book as a whole. In it rests the sum of the hundreds of hours I spent listening to the saddest music in the world. I pulled from all genres--jazz, rock, classical, country, etc.--and across six centuries, and to avoid a list dominated by Leonard Cohen, Billie Holiday, Elliott Smith, and Townes Van Zandt I stuck to a one-song-per-artist rule. Historical import, crowd-sourcing, straw polls, and my own listening, contemplating, listening again, and second-guessing were all factored into my decision making process.
Here, for argument, applause, and derision, is an excerpt, the tip of the iceberg, of my top 100 saddest songs ever.