1) If I could sing like anyone, it would be ... Norah Jones. I love her voice; it's so expressive. I don't think I could pull this off (not in a million years) but it's fun to dream anyway.
2) I would love to sing the song ... "Don't Know Why." She does a fantastic job of it on her first album. Actually, if I had tried out for the a capella group I wanted to my senior year of college, that would have been the song.
3) It would be really cool to sing at ... oh, I don't know. Not in front of lots of people (though if I had a voice like hers, I suppose it wouldn't be a problem)!
4) If I could sing a dream duet it would be with ... I have two: Tony Bennett, or Dan Haseltine of Jars of Clay.
5) If I could sing on a TV or radio show, it would be ... not American Idol! (I wouldn't want to humiliate myself). If I was good, and a good dancer, and had a good stage presence, the new Grease show would be fun (though Grease isn't one of my favorite musicals).
EDIT: Reading Songbird's Friday Five made me realize that I, too, would love to sing with Garrison Keillor on A Prairie Home Companion.