"Two short years" by Rodgers and Hammerstein. Ted Chapin introduced me to this song, I believe, many years ago. Just the most absolutely perfect, wise and complete lyric I have ever sung: Two short years Are not much time In the age of an infinite world. Two short...
"The Fall," the finale of Queen of the Mist. I am biased, because this musical was written for me, but I cannot listen to it without crying buckets. Queen is by Michael John LaChiusa, and as far as I am concerned, he is a genius.
"Sometimes It Snows in April." Prince. My heart broke the day Prince died. Such a genius. This is another wise, sad song. I love it so much, it is on my album, Have Faith with Micheal Starobin. (Shameless plug). And here's my take with Michael Starobin:
Tony Bennett singing "Here's That Rainy Day" by Johnny Burke and Jimmy Van Heusen. Nobody loves a sad song more than me. Exquisite. And nobody does what Tony Bennett does. Nobody.
"Daybreak" by Adam Guettel from Floyd Collins. I must have listened to this at least 800 times. To my ear, it is a spectacularly sad song, which I love, and Christopher Innvar and Jason Danieley's performances are heartbreaking.