Which ones do you most want to recommend?
You could do a top 10, a top 3, or whatever you like. Tangentially political is fine: To Kill a Mockingbird, or Rise and Fall of the Roman Empire, e.g., as long as the value you're seeing in it is political.
Here's my 12 (!) Top Ten political books:
Lies My Teacher Told Me: how everything you learned in public school about American history is wrong. Told me things I surely didn't know. What was the War of 1812 about? When did the first slaves cross the Atlantic? What was the number one budget item in Pres. Washington's administration?
How Civilizations Die (And Why Islam Is Dying Too), David Goldman. Fear not the hordes of Islamic terrorists (or Islamic non-terrorists) outpopulating and conquering us; fear the instability in the region as they give up hope and enter demographic and economic collapse. Egypt first.
Destiny Disrupted. How Moslems view world history.
America Alone/After America. Wag Mark Steyn details how first Europe, and now America, have decided to give up freedom and prosperity for infighting and bureaucracy.
Infidel. The life story of Ayaan Hirsi Ali, a Somali woman raised as a devout Muslim, who fled a forced marriage to the Netherlands, became a citizen, then an MP (!), and then found that her friend Theo van Gogh was murdered with a note stabbed into his chest that said, basically, "Ayaan Hirsi Ali, you're next."
The Enemy Within. Dinesh D'Souza argues that the failings of the American left and right render us incapable of not pushing peaceful Moslems toward support for terrorists.
The Roots of Obama's Rage. D'Souza uses Dreams from My Father and Obama's history to show the influence of Obama Sr. on Obama's political plans.
Rules for Radicals. Self-proclaimed 60's radical Saul Alinksy shows how to effectively push for what you want, with tactics I now see from both sides of the aisle.
The Fourth Turning. Cycles in US history, especially the last one starting around 1945, that lead to crisis, resolution, and change -- and how they affect the character of the generations within them.
Why Nations Fail: The Origins of Power, Prosperity, and Poverty. Using examples from the US, Mexico, Ethiopia, Argentina, the Dutch East Indies, and southern Africa, this book shows how successful economies are built or prevented -- and makes the interesting claim that our freedom is partly the accident that when colonies like Virginia got started, it was easy for the oppressed to run away.
Economics in One Lesson. Why all economic policies cost money, including the ones that are supposed to make us rich.
Agreed with your first, really enjoyed Lies My Teacher Told Me
For me a lot of them are on the other end of the political spectrum and usually involve more humor.
Enjoyed most of Frankin's books, like Lieing Liars as well as Rush Limbaugh is a big fat idiot
Years and years ago I picked up for dirt cheap a great one from James Carville called Fighting Back
Also the New Rules books from Bill Maher both humor and some good insights.
Created Equal: Why Gay Rights Matter to America. Makes the case I shouldn't have to beg others for my rights. Opened my eyes.
The Cross in the Closet. Straight conservative man who lived a year pretending to be a gay man to learn empathy. It transformed him as a man and as a Christian.
Their Own Receive Them Not: African American Lesbians and Gays in Black
Churches. Shows the hypocrisy of the black church with it's displays of homophobia.
Lost Prophet: The Life and Times of Bayard Rustin. The gay man behind Martin Luther King that history tried to wipe out.
End the Fed by Ron Paul
The Constitution in Exile by Judge Andrew Napolitano
A Patriots history of the United States by Larry Schweikart
Liberty Defined by Ron Paul
Also a lot of war books, such as Lone Survivor, No Easy Day, American Sniper, Marine Sniper, Outlaw Platoon, they are very informative about foreign policy and military engagements overseas
Most of the political reading I've done is for college. So most of the members of my list I will only have read in part, and they will also be well-known to you all.
"Is There a Duty to Obey the Law" co-authored by Christopher Wellman and A. John Simmons. Wellman's 'Samaritan' theory for legitmate state coercion interests me. Simmons' scholarship impresses me, but I found his 'philosophical anarchism' unpersuasive.
"The Federalist Papers" by Madison, Hamilton, and Jay. The essays are both historically significant and philosophically weighty. These men were geniuses
"Leviathan" by Thomas Hobbes. A few things I enjoyed about reading Hobbes were his clarity and his occasional humor. One portion of Leviathan that made me chuckle was his argument for the equality of mental capacities. He states something to the effect that there is no better sign of an equal distrubtion among persons than each being content with his own share, suggesting that men tend to think of themselves as being just so smart. Also, reading Hobbes (or at least those most famous portions) was helpful in having a richer understanding of the Federalist Papers. I was able to read a definite Hobbesian strain into Publius, particularly those essays attributed to Hamilton.
"Two Treatises of Government" by John Locke. Here's an important work. I don't think anyone could understand the theorectical underpinnings of the Declaration aright without having read this first. I think Locke's theory paints a rosier picture of human nature and restrains more the power of government than does Hobbes. Also, inherent natural rights is much more appealing than rights by convention. These ideas, along with our liberal heritage, make Locke's theory teneble to modern readers. So, it's not suprising to see Locke invoked in political arguments still, though perhaps a little ironically given the rise of natuaralism. I wonder how it is that naturalists can account for natural rights? I'll have to ask my atheist libertarian friend where he thinks his rights come from.
I might add more later.
PJ O'Rourke: On the Wealth of Nations (gives a good overview of Smith's famous book)
PJ O'Rourke: Don't Vote, It just encourages the bastards (good look into American politics without taking itself too serious)
I have not read enough political books to comment fully I think.