My fovorite would have to be Wicked, probably because it was the first (and only, as of now) Broadway show I've seen, and I saw it with the original cast, AND through a connection of my mom's friend I got to sit in the fifth row. It was basically awesome.
Another one I like is one I'm sure most of you haven't heard of, called The Roar of the Greasepaint, the Smell of the Crowd. I know, it's a mouthful. It was performed at my school last year, and it was quite different from anything I'd ever seen. It was about two people playing the game of life, and there were urchins, and it was all very odd. I wouldn't have understood it at all if my friend, who played an urchin, hadn't told me what urchins were. Then, I got the entire play.
As far as movies go, Sweeney Todd, definitely! Haven't seen it performed, though I would like to get my hands on the Angela Lansbury production of it (because Angela Lansbury just rocks). I think Burton's film was done pretty well, and Johnny Depp singing? Come on now.
Also, Disney movies.
And of course Once More, With Feeling. Gotta love that.