There’s a pain goes on and on.
NOTE: To avoid oversaturating this list with too many songs from the same shows, I limited my choices to one song per musical. The songs are presented in semi-random order, not ranked. Tissues are needed for all.
"You'll Never Walk Alone" (Carousel)
Sure, this is a song of hope, but like most songs of hope, it's sung in a moment of utter despair. And it won't bring Billy back.
"Losing My Mind" (Follies)
Nothing breaks your heart like unrequited love. Scratch that — nothing breaks your heart like Sondheim writing about unrequited love.
"Till We Reach That Day" (Ragtime)
You'll start crying the moment Brian Stokes Mitchell lets out that anguished scream. (But you'll probably already be crying, because Ragtime.)
