5. THE MEDIUM IS THE MASSAGE: An Inventory of Effects
Marshall McLuhan, Quentin Fiore, Jerome Agel, revised edition cover art by Shepard Fairey 
To me, this is a must-have handbook for every designer and technological history junkie. The book is composed in an experimental collage style with text superimposed on visual elements and vice versa. It is an experience of our global society, describing the networks of the social and technological world easily 20 years before it was defined. The book seems to predict—through fragmented discussion with the author—the emergence of the information age, the creation of new and large communication networks, with advanced technology that will eliminate time and space and blur together personal connection so that it is no longer quantifiable.
Some say that it predicted the awareness of the Internet, or, the conception of an extensive virtual network, in 1967—well before a concept like the Internet even existed.
Amazon Reviews says, “With every technological and social advance, McLuhan’s proclamation that ‘all media work us over completely’ becomes more evident and plain.”
During the 1960s media theorist McLuhan discussed television and the social actions that people exhibit when they are communicating through virtual media. He pioneered the field of media studies, however controversial it (still) may be.
4. THE COMPLETE TALES AND POEMS OF EDGAR ALLAN POE
Edgar Allan Poe [1830-1880]
From the Tell-Tale Heart to the Raven to The Bells, this classic anthology includes the original Gothic Tales of psychological horror, often covertly representing the mad genius and tormented artist, Poe himself.
-The Tell-Tale Heart
-The Fall of the House of Usher
-The Pit and the Pendulum
-full-length novel 'The Narrative of Arthur Gordon Pym of Nantucket'
3. NAKED LUNCH
William S. Burroughs 
If you want to probe the horrific mind of warped and ugly drug addictions, this is the place. "'Naked Lunch' has become one of the most important novels of the 20th century. On the relationship of art and obscenity, and on the shape of music, film, and media generally, it is one of the books that redefined not just literature but American culture. This is a story about the overwhelming, consuming, non-human experience of drug addicts, that becomes animated into a dreamlike interzone.”
Burroughs’ remarks on the main character: “His days, when they are not spent in desultory work or experiments with bug powder and other substances, are devoted to aimless sessions of cynical talk, delivered in perfunctory monosyllables.”
True to his cut-up style, “Burroughs stated that the chapters are intended to be read in any order.”
Reviewer Roger Ebert remarks, “While I admired it in an abstract way, I felt repelled by the material on a visceral level.”
2. HOUSE OF LEAVES
Mark. L. Danielewski 
I painstakingly read this book over New Year’s one year. With equal fascination and discomfort, it is impossible to explain.
'House of Leaves' is a horror story, about a story about a documentary film, about a never-ending black hole of a hallway, about a reader of a writer’s story.
It is also a research paper, a twisted love, a typography trip, and a look into an insane man’s mind.
The whopping 700+ page journey requires a lot of time, willingness and an open-mind. The first page ominously warns the reader: “this is not for you.”
This is what Wikipedia reviewers had to say: “The format and structure of the novel is unconventional, with unusual page layout and style, classifying it as ergodic literature. It contains copious footnotes, many of which contain footnotes themselves, and some about reference books that do not exist. Some pages contain only a few words or lines of text, toward the journey into the book; the typography text is arranged like abstract art— in strange ways to mirror the events in the story, often creating both an agoraphobic and a claustrophobic effect. The novel is also distinctive for its multiple narrators, who interact with each other throughout the story in disorienting and elaborate ways. The novel quickly became a bestseller.”
It is so strange that there are forums about it everywhere.
Check it out:
1. THE PASSION ACCORDING TO G.H. (A paixão segundo G.H.)
Clarice Lispector 
"A world wholly alive has a Hellish power."
Regarded as a work of philosophy after its publication in France, this is a twisted look into the confines of a psychotic woman’s empathetic inner mind. Every sentence is charged with more confusion, rushing headlong into an insane journey of self-realization. This novel takes readers through the identity crisis of a woman, which morphs into a trip through the interior of the novel itself.
“Before I entered the room, what was I?” G.H. asks. “I was what others had always seen me be, and that was the way I knew myself.”
"Hold my hand tight, because I feel that I’m going. I am again going to the most primary divine life; I am going to an inferno of brute life. Don’t let me see because I am close to seeing the core of life – and … I am afraid that in that core I won’t know anymore what hope is.”
This book continues to impress me for it's artistry in writing, concept, and brilliant execution.
See what the New York Times has to say about it here.