Here are some songs that came to mind, varying degrees of tear-jerking, hopefully you can use them
"Bring Him Home" - Les Mis
"Lost in the Waves" - Out of Our Heads
"What You'd Call a Dream" - Diamonds
"Losing My Mind" - Follies (could be either gender)
"Larger Than Life" - My Favorite Year
These are the ones that came to mind, but I'll post more once I think of them. I too am a sucker for sad and emotionally draining show-tunes. Also, listened to "Pretty Funny" for the first time, and wow, added to my iTunes.