I was a different person before and after I had read those books, and now I categorise all works of fiction into those that forever alter my way of thinking and those that do not.
Which reminds me, I should finish: https://en.wikipedia.org/wiki/Orthogonal_(series)
The Culture series by Iain Banks, especially Inversions also satisfy this requirement, as does The City at the End of Time by Greg Bear: https://en.wikipedia.org/wiki/City_at_the_End_of_Time -- which is a difficult to consume masterpiece that nonetheless left me permanently horrified in the way that H. P. Lovecraft tried but failed.
For the non-fiction category the CGP Grey video "The Rules for Rulers": https://www.youtube.com/watch?v=rStL7niR7gs
and Part 2: https://www.youtube.com/watch?v=ig_qpNfXHIU
have totally changed the way I look at all political discourse, and this is coming from someone who has already absorbed The Prince. It's based on the Dictator's Handbook, which I should read also, but the CGP video was an effective summary already!
Last, but not least, if I'm allowed to include lecture videos, then the "Arithmetic, Population and Energy" lecture by Al Bartlett is absolutely amazing. You will never see the news in the same way again after watching it: https://www.youtube.com/watch?v=O133ppiVnWY
If you want the hardcore game theory version, check out The Logic of Political Survival by the same authors: https://projects.iq.harvard.edu/gov2126/files/bueno_mesquita...
If governments and corporations haven't already started buying influence, I'd be shocked.
And a general +1 for GEB. If you read that as a teenager, you are different for it.
"The Dictator's Handbook"  does a good job of explaining various political systems lays down and presents an argument for why people in democracies have more freedoms and are generally more prosperous.
His "Rules for Rulers" video is an excellent summary of The Dictator's Handbook , itself a summary of well-regarded selectorate theory . I have yet to watch a CPG Grey video which does not honestly separate fact from opinion, and ensure the former is well sourced.
His delivery is excellent. But that, alone, is not substitute for well-written and -researched material.
 The Dictator's Handbook: Why Bad Behavior is Almost Always Good Politics
 The Dictator's Handbook: A Practical Manual for the Aspiring Tyrant
Fascinatingly relevant right now.
To add to this, administrators know if they don't hire extensively they are likely to be replaced by someone who will. There is no control mechanism. Giving students a small periodic vote in respect of their top administration would go a long way towards ameliorating such corruption.
The "Dictator's Handbook" covers such topics https://www.amazon.com/Dictators-Handbook-Behavior-Almost-Po...
Right now, Hong Kong is way too valuable as an economic engine, but the political dangers are more pressing to the CCCP. So the government will clamp down on freedoms as best they can until the citizens can't take it anymore, then keep beating the horse until it's dead.
You should read the book The Dictator's Handbook if you want to understand it better.
Provides compelling case that all politicians tend toward dictatorship with the difference in how fully these tendencies are realized just being in the size of the coalition they have to appease, reward, or bully. With stereotypical absolute dictators this easy to see. On the other end of the spectrum, it is more shrouded. American democracy is theoretically based on a maximum sized coalition equaling roughly the entire population. In practice, the leaders are beholden to and have to influence a much smaller coalition to wield power. Something like the current Sanders/Clinton popular vote vs inner circle super delegate issue demonstrates this pretty well. Fascinating read.
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