Last night, Cope and I got into a discussion on the show about how the media has painted a terrible picture of anarchy and how the misrepresentation really damages what is actually the most peaceful ideology that I have come across. Today while browsing the twatter to promote HIVE and see what's going on during the pre-post-apocalyptic throw-down, I noticed 
That being said, I promptly ran into problems trying to create a book list to share with the twatter crowd, and after spending way too much time trying to figure out why I can't get it to work and share properly, I've decided why not just post it to the chain and share the post. Kill two birds with one stone as they say right? Well anyway, here's some really great books and links to their GoodReads' pages that are spectacular entryways into Anarchy and then some that will dive much deeper into the fundamentals and propose solutions and alternatives to the current society that we live in.
I'll do my best to sort them in a loose "beginner" to "advanced" order, but honestly they're all great and if reading about philosophy is something that interests you, then you really can't go wrong, without further ado:
On Anarchism by Noam Chomsky is my personal pick for really getting a feel for what the core tenets of anarchy are really about. Chomsky is a legendary author and one of the foremost thinkers that really helped to spread the message and enlighten many people, no list of books on anarchy would be complete without his works.
Manufacturing Consent is a collaborative work of Edward S. Herman and Noam Chomsky that really dissects and breaks down the ways in which the media brainwashes the masses into submitting to the political machinations that we are all subjected to today.
[Anarcho-Syndicalism Theory and Practice] by Rudolf Rocker is quite simply put a masterpiece for those trying to explore alternatives to the current system we see dominating the U.S. and most Western countries. As a long-time fan of the ideals of anarcho-syndicalism, I consider it fundamental reading and if nothing else it's a good way to challenge your own beliefs and indoctrination toward capitalism.
(No, I'm not a commie, just keep an open mind that there can be something different than socialism, capitalism, and communism and you might really enjoy it.)
If you haven't heard of Bertrand Russell, he's probably one of the most iconic philosophical writers of recent years. Proposed Roads To Freedom is a great brook for exploring many different alternatives than just anarchism. I think the book is a powerful read because it doesn't just focus on any one particular ideology, but discusses the various benefits and problems with each and overall encourages the reader to think critically and figure out what is right for themselves.
As much as I love Anarchy, State, and Utopia by Robert Nozick, I will fully admit it isn't for everyone. While the author is overtly neo-liberal, I think the book is a great tool for breaking down and challenging our own beliefs. Different perspectives can be really valuable for growing our own perspectives and while many people outright hate the book, it's a good read in my opinion and great for advanced readers of anarchistic literature.
Daniel Guérin's No Gods No Masters is a great collection of anarchistic works and a good resource for those that are ready to dive deeper into anarchism. It won't read like a novel, but that's okay because you can pick and choose different sections that interest you. The quality of the works do tend to vary, but on the whole it's still a good read.
Last, but certainly not least, we have to talk about Black Flame by Michael Schmidt and Lucien Van Der Walt. I am putting this one last as I feel like you will probably need a firm grasp of anarchistic fundamentals to really enjoy it and learn anything from it. It's a very contentious book to say the least, but it explores several examples of anarchistic influences on multiple regions throughout recent history and it doesn't pull any punches. It's not all nice and it ain't all pretty, but it is very thought provoking.