If you are interested in the web, both these books were good: http://www.amazon.com/Python-Web-Programming-Steve-Holden/dp... http://www.amazon.com/The-Definitive-Guide-Django-Developmen...
Here are a few books that cover some "advanced?" topics that I'd like to read when I have time (would also like to hear other peoples' recommendations on them): http://www.amazon.com/Python-Data-Analysis-Wes-McKinney/dp/1... http://www.amazon.com/Twisted-Network-Programming-Essentials... http://www.amazon.com/Foundations-Python-Network-Programming... http://www.amazon.com/Introduction-Tornado-Michael-Dory/dp/1... http://onlinebookplace.com/programming-computer-vision-with-...
I'm not sure on your background or the quality of these books, but an understanding of data structures, algorithms, and object oriented programming could be considered important: http://www.amazon.com/Data-Structures-Algorithms-Using-Pytho... http://www.amazon.com/Python-Algorithms-Mastering-Language-E... http://www.amazon.com/Python-3-Object-Oriented-Programming/d...
Although these and other intermediate to advanced topics tend to be covered better in non-language-specific books such as this shotgun blast to the head. Don't worry, it's just an "introduction": http://www.amazon.com/Introduction-Algorithms-Thomas-H-Corme...
Looking to dig deeper into protocols described in the book, I just started reading Foundations of Python Network Programming and it seems to be providing that a more theoretical understanding of networking protocols that are so central to many modern hacks:
http://www.amazon.com/Foundations-Python-Network-Programming...