These 20 novels have libertarian themes such as human freedom, voluntarism, individualism, or anti-statism. Many other themes are present too. Some of the authors are themselves libertarians, some are not. No author is listed more than once. The order of the list is meaningless.
 Robert Heinlein’s The Moon is a Harsh Mistress (1966). This is the critically acclaimed book that inspired a young David Friedman to write Machinery of Freedom in 1969. All libertarian themes are at the forefront, told by a skilled writer at the peak of his creative powers.
 Yo Hua’s To Live (1993). The most human book I’ve ever read on the subject of life in Maoist China. We shouldn’t forget the lives destroyed by total statism in such a recent history, when that fanatic death cult controlled much more than North Korea.
 Ira Levin’s This Perfect Day (1970). Here, Ira Levin, author of The Stepford Wives and Rosemary’s Baby, gives us a false-utopia vision of the future where the State attempts to manage everyone’ lives through a supercomputer. Great book, very libertarian, and a nice antidote to utopian technocrat Zeitgeisters.
 Albert Camus’ The Plague (1947). This is the most political novel Camus wrote. Deserves its extremely good reputation. Individualism, freedom, community, and voluntary self-sacrifice are everpresent themes; libertarians will want to pay close attention to the character Raymond Rambert.
 Kurt Vonnegut’s Welcome to the Monkey House (1968). This is actually a collection of short stories by the legendary Vonnegut. All are good, but of special interest here is “Harrison Bergeron,” the story of a society in which the State has succeeded in making everyone equal… almost.
 Ray Bradbury’s Fahrenheit 451 (1953). A classic on statism, government censorship, mass apathy, and individual dissent.
 Mario Vargas Llosa’s Captain Pantoja and the Special Service (1973). Very funny satire on government bureaucracy. Masterfully uses humor to get serious points across. Llosa won the Nobel Prize in Literature for his work last year and he’s an outspoken libertarian - he’s even written articles for Reason magazine.
 Czeslaw Milosz’ The Captive Mind (1953). This novel gives you total statism from the perspective of true believers. Milosz (a Polish poet who won the 1980 Nobel Prize in Literature) wanted to get inside the heads of the communists, to expose their thought processes, and he does so brilliantly.
 J. Neil Schulman’s Alongside Night (1979). Excellent novel describes the last two weeks before the collapse of the US government, and its happy aftermath.
 George Orwell’s Animal Farm (1945). If you’re a libertarian and you haven’t read this, you probably should.
 Aleksandr Solzhenitsyn’s One Day in the Life of Ivan Denisovich (1962). Another Nobel winner. One day in the life of an individual in the Soviet gulag. Devastating and hopeful.
 Alexandre Dumas’ The Count of Monte Cristo (1844). Themes in this classic are clear: retribution, freedom, fate, and the corruption of the State. “It seems to me the first care of government should be to set at liberty those who have suffered for their adherence to it.”
 Young-ha Kim’s I Have the Right to Destroy Myself (2007). South Korean novel touching on suicide, its criminalization by the State, and the primacy each individual has over knowing “what’s best” for him. A slightly depressing but very very well-written, thought-provoking book.
 J.R.R. Tolkien’s The Lord of the Rings (1955). Tolkien was a libertarian anti-statist and couldn’t help reflecting that in his epic, as he put it: “The story is cast in terms of a good side, and a bad side, beauty against ruthless ugliness, tyranny against kingship, moderated freedom with consent against compulsion that has long lost any object save mere power.”
 Franz Kafka’s The Trial (1925). Classic, bleak, mind-numbing, account of the individual human being lost in the mindless machine of government.
 Aldous Huxley’s Brave New World (1932). Another classic, thoroughly libertarian, and amazingly well-written.
 Ayn Rand’s We the Living (1936). Rand’s first novel. Anyone who doesn’t think Rand was a skilled writer should read this. It’s good. She wrote it before fully adopting her ‘Objectivist philosophy,’ which is not libertarianism and which I find seriously misguided. Anthem (1937) is a reasonable novella and the best introduction to that side of Rand.
 F. Paul Wilson’s An Enemy of the State (1980). Brilliant book about anti-statists who bring down an empire using black markets.
 Eugene Richter’s Pictures of the Socialistic Future (1893). Neglected novel about a socialist in Germany who witnesses the horrors of full-blown socialism. Reasonably well-written. What’s really impressive is the accuracy with which this book details the actual results of state socialism - decades before they actually began to occur. The Mises Institute has republished a good translation.
 E.E. Cummings’ EIMI (1933). This is, by far, the most challenging book to read on my list. Cummings was primarily a poet and this novel is written in an unusual stream-of-consciousness style that can be hard to follow. However, once you get used to it, it’s effective. Cummings was a young leftist artist coming out of Harvard, where many of his friends considered the Soviet Union a progressive utopia in the making. He went to see for himself and came back no longer a leftist. EIMI is his novelization of those travels through early communist Russia, and its a striking case for human freedom and against statism.
I should add to this list at a later time. :)