These are my favorite books and book-like texts, revised in 2014 to reflect my shifting interests. I haven't turned the titles into buy-links because I don't want to endorse any seller. For reviews I recommend Amazon and Goodreads, and for getting the books I recommend libraries, e-book downloads, or local bookstores if you have the money.
Big Ideas
Most of my thinking could be derived just from Ivan Illich and Charles Fort. Illich wrote critiques of modernity, and he was so smart, and wrote so clearly, that reading him is like looking at the sun. His best single book is probably Tools For Conviviality. Here's a good source of Ivan Illich writings online.

Charles Fort was the first paranormal investigator, and he's my favorite natural philosopher. He spent 27 years in libraries collecting notices of physical phenomena unexplainable by science, and put them together into four books in the 1920's. You don't have to be into weird stuff to appreciate his style of thinking: that all our attempts to make sense of the world only seem true by excluding stuff at the edges that doesn't fit, and we can keep updating and revolutionizing our models to fit new observations, but there is no end to this process. This should not make us feel troubled, but awe-struck and amused. The Book Of The Damned is Fort's first and best book, and his one-volume Complete Books are still in print. Here's another source of Fort online.

I used to think that human society was approaching permanent collapse. I changed my mind when I learned to distinguish between economic, political, and technological collapse, and realized that the arguments for the latter are completely hand-wavy. But if you want to read about what's wrong with industrial civilization and why it seems to be doomed, I recommend William Kötke's The Final Empire. Here's a link to the whole text online, but you can only get to each chapter from the end of the previous chapter. Also Kötke has a newer book, Garden Planet, basically a streamlined and updated version the same stuff.

I also used to be into the primitivist critique of civilization, but now I consider it a motivational idea (it's optimized for strong emotions rather than understanding) based on a semantic fallacy. It goes like this: 1) Define "civilization" in terms of the worst behaviors of large complex societies in the past. 2) Describe all possible large complex societies as "civilization". 3) Therefore large complex societies can never be done better and we should give up on them. If you're into this idea, you probably already know about Daniel Quinn and Derrick Jensen. A lesser-known book is Rogue Primate by John Livingston. I covered it in The Animal in the Dark Tower, and here's Dan Bartlett's summary of Livingston. He challenges the primitivist orthodoxy by putting the key mistake not at the invention of agriculture, but the invention of fire!

The smartest and most beautiful book about civilization is Against His-story, Against Leviathan by Fredy Perlman. He doesn't have a program to save the world -- he just goes through all of history explaining how control systems have developed and changed, and why people have always rebelled against them. The style is difficult but it's worth it. The whole text is online, and you can also buy it from Black and Red Books.

Another good author on these subjects is Morris Berman. My favorites are The Reenchantment Of The World, which covers the metaphysical impoverishment that came with modernity, and Wandering God, which makes an important distinction between settled and nomadic culture.

Shifting into philosophy, The Lazy Man's Guide To Enlightenment by Thaddeus Golas is a tiny book with high value per page, and a big influence on my thinking.
Dropping Out
The phrase "drop out" is motivational: it generates strong emotions by giving people an idea that doesn't fit reality. A book that amplifies this error is Days of War, Nights of Love by the Crimethinc collective. This kind of writing is fun, and it could be useful to get your mind outside the dominant value system, but it's harmful if you take it as serious advice.

In reality, trying to get completely outside society will end in disaster, and the last thing you should aim for is purity. It's best to remain "in the world but not of it." This is largely a matter of mental discipline: remembering who you are, valuing yourself without reference to conventional social status, and avoiding traps for your time and attention that seem required but are really optional.

The best book to start with is Your Money Or Your Life by Vicki Robin and Joe Dominguez.

If you want to give your kids a head start, check out The Complete Home Learning Source Book by Rebecca Rupp, and The Teenage Liberation Handbook by Grace Llewellyn.

Living on the fringe requires the ability to self-motivate. A good book covering the latest science of motivation is The Willpower Instinct by Kelly McGonigal.

Practicing mindfulness ("meditation") will also help. My favorite author on this subject is Charles Tart in the books Mind Science and either Waking Up or Living the Mindful Life. Also check out Cheri Huber, and either The High Performance Mind or Awakening the Mind by Anna Wise.

If living on the mental/cultural fringe does not feel meaningful enough, and you insist on living on the physical fringe, you could try joining an intentional community. The best source of information is the Communities Directory, and here's the Communities Directory Online.

If you want to buy rural land and build your own house, check out Mortgage-Free! by Rob Roy. And the best book on buying land is Finding & Buying Your Place in Country by Les Scher. A good book for homesteading and general self-sufficiency is Carla Emery's Encyclopedia of Country Living. For house-building I recommend cob, and I like Becky Bee's Cob Builders Handbook better than The Hand Sculpted House. That book tells you what you should do, and Becky tells you what you can do.

My advice is, if you can afford all that, you can afford to buy an already existing house on an urban lot in a declining city like Buffalo or St. Louis, where you don't need to drive 20 miles to get anywhere. Then you can still plant a few fruit trees and berry bushes and grow some annuals like tomatoes to supplement the low-quality industrial food that will remain cheap to prevent violent revolution. Good books on gardening: The Resilient Gardener by Carol Deppe, Gaia's Garden by Toby Hemenway, and How To Grow More Vegetables by John Jeavons. If you want to get really advanced, look for Bill Mollison's Permaculture, a Designer's Manual, also published as Permaculture, a Practical Guide for a Sustainable Future.
Woo-Woo Stuff
I've been into paranormal and new age writing for most of my life. My advice is not to exclude it completely or your mind will become cramped and inflexible. It's safe to dip your toes into it, but if you go into it deeply, you have to commit to going all the way through. Because you'll reach a point where your mind cracks open and you'll think you suddenly Know the Truth, and you'll be tempted to stop and set up camp. You must not stop, but keep looking at different perspectives. Then you'll think, wait, now this is the Truth, and now this... Hold on here! It's looking like reality itself is so packed and multifaceted that it's easy to make any nutty system of thought seem like the Truth -- including the dominant paradigm itself. Now you're getting it!

The smartest and most thorough book on the "paranormal" is The Trickster and the Paranormal by George P. Hansen. Even though his writing style is aggressively clear, it's still hard to read because the ideas are so difficult. He covers anthropology, literary theory, shamanism, stage magic, UFO hoaxes, psychic research, and more, and the general idea is that it's the very nature of these phenomena to only exist on the fringes. How can this work? The answer is simple but sounds so crazy that even Hansen only hints at it. Another big idea is that real unexplained phenomena and hoaxes are not opposites, but blend together.

I love the books of Fortean paranormal researcher John Keel. They're all great, but my two favories are The Mothman Prophecies and The Complete Guide to Mysterious Beings. Like Keel, I think UFO's are an occult phenomenon (which means something very hard to explain), and an even smarter author who thinks like this is Jacques Vallee, whose most important book is Passport to Magonia.

A great source for all kinds of fringe books is Adventures Unlimited.

Some books that try to merge woo-woo stuff with hard science: The Holographic Universe by Michael Talbot, The Field by Lynne McTaggart, and The Self-Aware Universe by Amit Goswami. And for a critique of the untested assumptions that underlie science as we know it, check out The End of Materialism by Charles Tart or The Science Delusion by Rupert Sheldrake.
Fringe Science
This category blurs into the above. I have the rational intelligence to be a scientist, but it's not in my personality to fill in cracks in established mental models. I seek anomalies that open cracks. William Corliss is an heir to Charles Fort in that he collects anomalies from respected sources. He doesn't comment on them but reprints them in many books, which you can browse or buy at Science Frontiers.

My favorite hard scientist is the astronomer Halton Arp. His books are Seeing Red and Quasars, Reshifts, and Controversies. Arp has spent his career gathering evidence that redshifts are mostly caused by something other than recession velocity (which could cancel the expanding universe and the big bang), and that quasars are not extremely remote and bright, but are associated with nearby galaxies, shot out to form new galaxies like seeds! When dominant astronomy couldn't counter him fairly, they eliminated his telescope time, and for decades he has been forced to use the discarded and suppressed evidence of his enemies.

I like Rupert Sheldrake, a biologist who writes popular books of hypotheses that are scientific in the sense that they are testable, but outside the bounds of present scientific models. Mostly he writes about different kinds of extraordinary perception, and explains them with ideas about non-local consciousness.

Some of the most exciting fringe science is done by single researchers who consistently get extraordinary results, and then when other scientists try to duplicate the experiments, the results fade away into randomness. This is called the decline effect and that link goes to a great article about it. This is exactly what would be predicted by a larger metaphysics that views reality as a consensus that emerges out of a struggle among many perspectives that want to share the same world.

So when Wilhelm Reich developed physical tools to work with the esoteric energy he called "orgone", or when Royal Rife cured serious diseases with precise frequency generators, or when Louis Kervran found biological creatures transmuting chemical elements (his book is Biological Transmutations), or for that matter, when ordinary people experience UFO abductions or miraculous healings, these are not hoaxes or delusions. They are honest and accurate observations that fail to be integrated into consensus reality... so far!
I loosely follow the Weston Price diet, for which the main book is Nourishing Traditions by Sally Fallon. It's a lot like paleo but includes grains if they're sprouted or soured, and it's big on fermented foods. The best book on that is The Art of Fermentation by Sandor Katz.

The best book on sourdough bread is Nancy Silverton's Breads from the La Brea Bakery.
Other Non-Fiction
I once heard about a book called Play as if Your Life Depends on It by Frank Forencich. It's a fitness book based on moving like natural humans, doing exercise so it's functional instead of repetitive, play instead of work. I should have bought a copy because now it's out of print and worth hundreds of dollars. But he has other books, and Paleo Fitness by Darryl Edwards is probably similar. I'm currently working through Brett Stewart's 7 Weeks to Getting Ripped, and it takes a lot longer than seven weeks!

Alice Miller's For Your Own Good is a very important book about the hidden child abuse in the first two years that we often think of as normal child-rearing, and how it ruins society. Another good book on the same subject is The Continuum Concept. Here's For Your Own Good online.

John Taylor Gatto's The Underground History of American Education is a massive, angry book about how American schools have been turned into mind-killing factories to churn out docile, unquestioning citizens and workers... not by accident or negligence but by the explicit planning and interference of the elite beginning in the mid-1800's.

My favorite history book is A Distant Mirror by Barbara Tuchman. I expect the 21st century to be similar to the 14th century: lots of poverty and general nastiness, but the big systems will muddle through and technology will thrive.
Fiction by guys named Philip
Philip K. Dick wrote more than 40 novels and basically invented trippy-reality sci-fi. A reviewer once remarked that Dick had so many ideas that he would just scatter ideas in the margins that other authors would hang whole books on. I recommend starting with The Game Players Of Titan because it's a fun page-turner with lots of plot twists. Then you'll be ready for stronger stuff in Ubik, and then you might be ready for his scariest and most powerful novel, The Three Stigmata Of Palmer Eldritch. Also great are Dr. Bloodmoney and A Maze of Death, and almost anything is going to be worth reading -- but I think The Man in the High Castle and Do Androids Dream of Electric Sheep are overrated. Dick himself said that A Scanner Darkly was both his saddest and funniest novel, and I agree. (It was also the first one he didn't write on speed.) The Valis trilogy is for readers more interested in Dick's personal life and beliefs.

I love Philip Reeve. The first sentence of Mortal Engines: "It was a dark, blustery afternoon in spring, and the city of London was chasing a small mining town across the dried-out bed of the old North Sea." The premise of the four-book series is that around 2000 years from now, most of the planet will be ruined and cities will move around and eat other cities for resources. Reeve has great ideas, good characters, lively prose, and a mature understanding of politics and evil. Probably his personality is exactly like mine.

Then there's Philip Pullman, whose most famous work is the trilogy that begins with The Golden Compass (aka Northern Lights). The books are set in a steampunky world combining old technologies with super-advanced ones, and there are parallel worlds and gateways. Metaphysically the story is shockingly radical, with the idea that God himself has become corrupted by power. The first book is great, and the second, The Subtle Knife, is darker and even better. The third book is a disappointing failure of imagination, with a feeble ending in which the effect of an epic upheaval in reality itself is that nothing changes.
Other Fiction
In what I call the "No Exit" scenario, civilizations continue to rise and fall with no release through either utopia or extinction. The best fiction about this is Gene Wolfe's Book of the New Sun series, starting with The Shadow of the Torturer. The story is set so far in the future that you can dig a hole anywhere and find strange artifacts from forgotten civilizations, and all the coolest Medieval stuff, high tech, and magic are all mixed together.

M.T. Anderson's Feed is the ultimate dystopian extrapolation novel, sadder than A Scanner Darkly, bleaker than The Sheep Look Up, and more readable than either. It's set two or three generations in the future, when the internet has become even more commercial and is beamed straight into everyone's head. Space travel and flying cars have only extended the range of the American nightmare, and almost everyone is stupid and immature. It's like if Lars von Trier had made Idiocracy. Also it has a great first sentence: "We went to the moon to have fun, but the moon turned out to completely suck."

I know three people including myself who have read Orson Scott Card's novel Treason, and we all think it's better than Ender's Game. Trust us. It's about a planet where a bunch of families were exiled, and over the centuries they have all basically developed different super-powers. I wish there were a bunch of sequels!

Roger Zelazny was one of the first sci-fi authors I read and is still one of my favorites. His early stories are brilliant and mostly forgotten, and the Amber series is like the Citizen Kane of parallel worlds fiction, but more fun. Another good one is Roadmarks, where a literal highway is used for time travel.

I love Raymond Chandler. His novels are beautifully written, and I like his early stories (collected in Killer In The Rain) even better for their power and pacing.

I mostly don't like the literary genre, but Cormac McCarthy is an exception. The Road is famous but All The Pretty Horses is a better one to start with, and his masterpiece is Blood Meridian. It will never be made into an adequate movie because no real person can play the Judge, easily the greatest villain of all time.

In theory I should like "magic realism" except that I don't like Latin American authors. But John Crowley's Little, Big blew me away with its beautiful language and otherworldly aura. It's like a whole other direction that fantasy could have gone. I wish there were hundreds of books imitating Little, Big, instead of hundreds of books imitating Tolkien.