A New Brain is probably his most accessible work. It's a semi-autobiographical story about a guy who has to have brain surgery... but it's totally peppy and hilarious. "Heart and Music" is one of those songs I play whenever I'm feeling depressed and it fixes it. "Sailing" and "And They're Off" are two of my other favorites.
Elegies: A Song Cycle is probably my favorite of his works. It... well, is what it sounds like, a series of songs written about people he's known in his life, and they range from hilarious to absolutely heartbreaking. My only warning is that a few of my favorite songs ("Only One" and "Infinite Joy" come to mind) are sung by Betty Buckley, who, though she emotes her way through songs wonderfully, can have some extremely annoying vibrato at times.
His sort of magnum opus, so to speak, is Falsettos. It was the Broadway show that actually combined two one-act musicals he did off-broadway, March of the Falsettos and Falsettoland. It's the story of Marvin, a man who leaves his wife for a man and tries to maintain his relationship with his son (and then, not to spoil anything, but... bad things happen). It's almost entirely sung through, ridiculously catchy, and so... I don't know, emotionally real.
And... that's a start!
"Why, I make more money than... than... than Calvin Coolidge! PUT TOGETHER!"
~Lina Lamont
My name wasn't, isn't, and will never be Scott.