Day 04—A song that makes you sad.
I'm going to cheat and put two, because I can't pick between them. Both of them are by Harry Chapin. My parents both love Harry Chapin. As the story goes, they were planning on going to the free concert Harry was going to give in New York when he had a heart attack on the Long Island Expressway. I grew up more on his brother Tom's cheerful (if borderline "black-footed hippie") children's music; I have infinite respect for Harry's master songwriting, but it seems that everything he does just about breaks my heart, so I don't listen to him as much as I should.
There's another video floating around on YouTube of him on Soundstage, doing a live performance. He gives a nice little intro to it, giving credit to his wife, and then he also echoes my sentiments entirely: "And frankly, this song scares me to death."
And here's the Soundstage performace of "Mr. Tanner," with a good long introduction. Based on a real review from the New York times of a debut singer, though with poetic license taken. I still can't listen to it without a lump in my throat.