A People's History of the US by Howard Zinn:
I read this as a liberal teenager who liked history and who was opposed to the war in Iraq. It undoubtedly played a large part in me moving from a Green Party liberal to an anarchist in a year and a half (which is not to say that my early anarchism wasn't activisty as fuck). The book is just so fucking inspirational and easy to read and authentic. When I got to university, it was also my default go-to first reference for any essay writing.
Now, I also have a theory that the Howard Zinn and this book may have single-handedly kept the IWW alive. The best written part of the book, by far, covers the time period from Haymarket through to the end of the Great Depression. You read that bit about the founding of the IWW with Big Bill Haywood speaking to the founding congress and Zinn quoting the preamble in its entirety and you do what I did: go google the IWW, find out the they're still around, and join up!
Seriously, I just can't recommend the book enough. I've bought maybe four or five copies as presents, I own two copies myself, and I've loaned out my copies at least half a dozen times. I even gave a copy to partner as a Christmas present one year.
9/11 by Noam Chomsky
As a teenager, it was the Iraq war that radicalised me. I found Chomsky at about that same time I found Zinn and I remember reading 9/11 and thinking, “My God, this is the first rational response to the attacks that places them in any sort of coherent historical and geopolitical framework”. As I've grown older, I'm developed a more critical attitude toward the Chomp, but the effect his work has had on me over the years can't be overstated. Also, we share a birthday and a friend had him send me a happy birthday email one year. Fucking wicked!
ABC of Anarchism by Alexander Berkman
After first getting interested in anarchism, I went to the Wooden Shoe bookshop and, on recommendation, picked up a copy of this book. Made me an anarchist. Don't really think much more needs to be said.
1984 by George Orwell
I was a mouthy little shit of a teenager and this meant that I ended up in “in school suspension” quite regularly. Within the first hour I'd complete the day's work and I'd have to choose from the small selection of books on the shelf in the room. One of those, luckily for me, was 1984. I must have read the book six times over when I was high school. Besides just being beautifully written and amazing and frightening piece of literature, the anti-authoritarianism of it certainly appealed to my 17 year-old punk rock self. Plus when we had to read Animal Farm and my teacher tried to tell us that it was about Orwell's rejection of socialism and call for (capitalist) democracy, I could use my 1984 knowledge to say, “Well actually Animal Farm is about Orwell's rejections of Stalinism, not his abandonment of socialist principles”. And being the cocky little shit I was, I enjoyed that.
Das Kapital by Karl Marx
The fundamental theoretical and analytical text for any communist (and I am a communist, anarcho-syndicalism is just the way to get there). Took me six months to read and the first three chapters were like banging my head against the wall. It's an undertaking, but you can't appreciate Marx only reading it in bits. I'd recommend reading it along with the David Harvey Lectures.
Homage to Catalonia by George Orwell
The book is a fucking anarchist wet dream. It reads like a novel and I don't think there's any other book that I've read that captures the romance and passion of the Spanish Civil War in quite the same way. (Although I've been told that Abel Pez's biography of Durutti is pretty riveting)
Strike! by Jeremy Brecher
This book sort of crystallised my critique of trade unionism and made me realise that workers didn't have to be organised into explicitly radical unions to pull off amazing self-organisation. That idea that 'action precedes consciousness' is rife throughout the book and its view of historical struggles really places into context the contemporary situation the class faces today.
If you do read it, I've heard that Brecher's earlier council communism has given way to social democracy and subsequent version of the book reflects that shift. So get an old version.
Punching Out by Martin Glaberman
Written about Glaberman's experience battling the union and the bosses post WWII auto factories, this is the best book, by far, for practical experience of shopfloor militancy and wildcat strikes. The book is incredibly accessible although the politics can be a bit strange at point. I think Glaberman identifies as a 'Left Trotskyist Syndicalist' or something like that. Still tho, just an incredible and inspiring read.
Libcom collective still has my copy, incidentally..
Lies My Teacher Told Me by James Loewen
Pedagogy of the Oppressed by Paulo Freire
The General Strike by Ralph Chaplin
Forces of Labour by Beverly Silver
Now, with all that out of the way, I feel I need a disclaimer saying that, practically, the best education in struggle I've had comes from talking to older workplace militants. As inspiring as A People's History of Strike! may be, it's the conversations with the folks that have been there on the front lines which I think prove the most valuable.
The libcom forums, at their best, can also be a place to share organising experiences. But it's getting stuck into organising at your own workplace and having that real person you can go to and have an actual conversation with that shaped my politics the most. After all, theory should be informed by practice and practice should reflect theory. Real-life conversations with real-life militants are the best way to push forward that dialectic.