Pick up a copy of the Village Voice (if it's still being published... I have a vague recollection that they stopped putting it into print, a terrible thing if true)... Anyway, if it is available it will have page after page after page of live music listings towards the back. IMO stay away from Times Square unless you want the Disney version of NYC. Great restaurants all around, especially Upper West Side, and East and West Villages. Hell, there's great restaurants on nearly every block in every district. Soho has also become quite commercial but it's still fun. I'd also avoid Little Italy for food... mostly tourist traps and there's great Italian to be found elsewhere (Arthur Ave. in The Bronx, for one place). Anyway, I'm a suburbanite. We've got some Brooklynites and Manhattanites among us, hopefully they'll chime in.