I'll only comment on the graphics stuff 'cos that's what I know.
I tend to divide graphic software books into 2 categories, both of which have value depending on your requirements. It's often good to have both kinds...
The first kind is the tutorial sort, where a disk may come with the book or sample files are on a website. These usually have step-by-step lessons that take you through a structured, deliberate course of lessons that introduce you to the workspace in a methodical way. The Adobe 'Classroom in a Book' series being a perfect example... however these are usually not too in-depth but are particularly good if you have never used the application before. This is where I started with Illustrator, working up to other stuff later...
The second kind is the 'Bible' where every technique, setting, and feature is discussed & explained. Far more indepth but less user-friendly for novices, they supplement the first kind when more detailed knowledge is required. They're the kind of books that you tend to dip into to refresh your knowledge on a particular technique. David Blatner is a highly recommended author of this type of book...
Sitting on my desk at work are: MacWorld Bibles for Pshop, Illustrator, Acrobat, and David Blatners 'Real World QuarkXpress'. In fact, I also recommend the 'Real World' series...
They're just handy when you're looking for that obscure keyboard shortcut or technical info.
EDIT: As far as Mac books go, the two most valuable ones I've purchased are OS X: The Missing Manual by David Pogue and Mac OS X Help Line by Ted Landau.