If you absolutely had to pick only 1 book to recommend...

lol @ people recommending 1984 and brave new world. Many current americans had to read those books in school growing up; looking around at the state of things i can only come to the conclusion that they thought the scenarios in those books sounded like a good idea.
 
George Orwell's 1984.

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That book is the book on the kind of government we are looking at now, and the kind of future we can expect if we continue to allow them to rule over us. Its applicability its frightfully correct.

^ This, or another great libertarian novel - An Enemy of the State by F. Paul Wilson
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For nonfiction, have to go with Liberty Defined by Ron Paul. :)
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Personally I would recommend a book that is non-fiction, based in history that explains why a freedom based economy, government and system is far superior to a collectivist system.

Fredrick Hayek - THE ROAD TO SERFDOM.
 
The Law

Followed by Liberty Primer, since nobody else has mentioned it.
 
It would depend on what their strengths and weaknesses were, and what their reading level was. But most of the time, I think it would probably be Economics in One Lesson.

The Law, probably due to the translations and original date of publication, is not really a fun or easy read.
 
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George Orwell's 1984.

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That book is the book on the kind of government we are looking at now, and the kind of future we can expect if we continue to allow them to rule over us. Its applicability its frightfully correct.

That is a fine book with a lot of very good themes, but it is only a Science Fiction novel.

It's good to have read that book when you want to participate on forums like these and know what people are talking about when they reference it, but you should not look at it as though it were a comprehensive guide to all things to avoid from government, because it's not.
 
I read 1984 when I was a young teenager and went on to become sort of a libertarian mutualist until many years later when I started learning about economics.
 
Stranger in a Strange Land

Not only possibly the greatest work of science fiction ever, but also a fascinating exploration of the virtues of individualism and the destructive nature of government.
 
The Revolution Manifesto was the book that really got me into Dr. Paul in 2008.... I was sitting at a friends house waiting on him, and read the first 15 pages, and couldn't put it down.... I asked "What course is this for?" assuming that a book like that was academic, and viewed Dr. Paul and libertarianism in a whole new light after that.

I still have a lot more advanced readings I'd like to do, so I also thank you all for the recommendations....

Also, Dr. Paul's Liberty Defined is also an outstanding beginner book on his views, with each issue divided into easily digestible 3-5 page chapters.
 
All awesome books. I wish these were the books I was required to read in public school..... Economics in One Lesson by Henry Hazlitt is, in my opinion, the best to start with of all these.
 
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