Henry Jenkins, Textual Poachers. Henry was my advisor in grad school (and my nominal advisor as an eighth-term undergrad), and MIT's Comparative Media Studies program has long had a cult-of-personality feel to it. Henry's a charismatic, intellectually-curious synthesizer and popularizer with a strong interest in pedagogy; he's impressively socially awkward but it helps that he's basically a professor of Popular Stuff. Textual Poachers was his first important book, maybe his most important; it revolutionized fan studies and taught two generations of scholars how to switch fluently between the insular codes of media fandom and the equally insular (but orthogonal) codes of cultural studies.
But it's important to recognize that Textual Poachers is a polemic, and its famously positive treatment of fan culture(s) is explicitly biased in favour of fans-as-ideal-media-consumers. Henry's strategy was necessary in those days - twenty years ago there was no serious academic discourse valorizing fans - and as the corporate co-optation of fan activity and the essentially consumerist approach of fans have been better understood, it's gotten harder to look at media fandom with Henry's optimistic eye.
That said, when I read this book a decade ago it changed my entire outlook on active audiences and the pleasures of collective intellectual engagement (nicely shielding me against Chomsky fandom, by the way). My ardor for this kind of study has cooled, and my dislike of the evolving standard cult-studies perspective on consumer/audience formations has overcome the rah-rah feelings I learned from Henry (thanks in part to the other key force in MIT CMS's early years, my mentor David Thorburn), but Textual Poachers remains an essential text for understanding fans and their place in the humanities.
Deleuze and Guattari, Milles Plateaux. A book this full of half-baked pseudoscientific metaphors and insufferable subliterary prose-gestures shouldn't be allowed into any classroom without a disclaimer. This book almost singlehandedly put me off critical theory in grad school (with a little help from The Postmodern Condition) but my first encounter with A Thousand Plateaus - rhizomes, flows-not-objects, the fashionable nonlinear allusiveness of it all - was one of the most exciting things ever to happen to my brain. A lot of ideas now dear to me can be found (in diminished form, drenched in parochial preoccupation) in this book, but the thing itself is unbearable unless you've subscribed wholeheartedly to the particular textual habits unique to French (or Francophile) critical theory coming out of the late 1960's. Its project is grounded in its style. Alas. Off the top of my head (even) I can recommend literally dozens of critical theory books more useful and worthwhile this one. But you had to be there, y'know?
Brian Sutton-Smith, The Ambiguity of Play. One of the best treatments of play and games I've ever read: a crucial overview not of play/game styles as such, but of rhetorics and understandings of play. Sutton-Smith's book actually deserves the label 'magisterial,' as it authoritatively synthesizes a large body of research on the social/cognitive worlds of play, childish and otherwise. My Masters thesis was preoccupied with textual forms (of video games), but Sutton-Smith helped jumpstart my thinking about games as interesting, emotionally-useful behaviour structures.
Andrea DiSessa, Changing Minds. Much of what I think about teaching and learning originated in this lovely little book, which set me searching for Vygotsky, Freire, Jim Gee, and other alternative pedagogues. When I figured out that one translation of 'changing minds' is psychotropism I experienced one of those moments nerds live for, where for a moment everything I cared about suddenly seemed to belong to a unitary body of all-knowledge. This book makes me feel less lonely.
James Austin, Zen and the Brain. Plenty of books share this one's intelligence-to-wisdom ratio - but few have such high absolute scores in each category, you know? I first looked at this book just a couple of years ago, and it's deeply colored my worldview ever since. If I could write a book half this good I'd die happy (or at least justified in my arrogance).
Clifford Geertz, The Interpretation of Cultures. Two essays in this collection - 'Deep Play: Notes on the Balinese Cockfight' and 'Thick Description' - are classics in cultural anthropology, and were foundational texts in the CMS program. I read 'Deep Play' as an undergrad; the realization that what amounts to Russian roulette with birds can be a central element of cultural life still haunts me. 'Thick Description' was an assigned grad-school text: people are nuts, cultures are nuts, and Geertz seemed to be proposing that literary understanding and representation could help us grok that nuttiness. I didn't know poetic permissiveness belonged in 'serious' academic work. Well, now I know.
Rick Perlstein, Before the Storm. This much-talked-about recent history of the Goldwater revolution and the birth of the modern conservative movement really had an effect on me. It taught me that the right-wing uprising of the Sixties, culminating in the tragic fantasy figure of Ronald Reagan and later vomiting forth the farcical George Bush, was nonetheless an expression of authentic popular anger - not a counterrevolution but a grassroots revolution in its own right. Goldwater was only politically defeated, the story goes - he and his boosters won the argument (or 'argument') on the far right. Before the Storm does more to humanize modern Republicans and conservatives than any 'conservative' writing of today, and Perlstein's affection for those loopy Goldwaterites suffuses every page.
And it's a lightning-quick read despite its heft. A wholly successful, unexpectedly deep book.
[Clarification: It's necessary for me to read books that 'humanize modern Republicans and conservatives' because I live in a media cocoon, having little to do with even the mass media like network TV, never mind conservative/Christian/Republican channels.]
Heidegger, Being and Time. No, I didn't get through it. Not even close. But the class I attempted it for, Gian-Carlo Rota's 'Being and Time' seminar, was one of the happiest experiences of my life. The class met from 7-10pm on Friday nights. I took it with perhaps ten of my housemates at Tep, and you must understand that none of us ever willingly missed the class. Rota introduced us to thrown-forwardness, the phenomenology of projects, inquiring into the nature of things through eidetic variation, the abyss between facticity and function ('meaning,' you might say)...above all about authenticity as the highest measure of thought. I stumbled into a B+ and barely touched the major assigned text (though I devoured Rota's essays in Indiscrete Thoughts), and 12 years later I still think and feel and wonder in the terms Rota taught me.
Janet Murray, Hamlet on the Holodeck. Not a great book, actually, but a foundational text for the CMS program (and Murray's present program at Georgia Tech). Yes, Murray's reading of Tetris is totally wrong, blah blah blah, but her ideas about digital narrative remain influential and her early computers-for-storytelling boosterism provided powerful motive force for early digital media studies in the academy. As for me, this book was maybe my first reading in media studies, and its narrative preoccupations encouraged me. Superseded since 1997 by plenty of other digital-culture writing, but along with other mid/late-90's media studies texts this was a big deal for me.
Martin Gardner, Wheels, Life, and Other Mathematical Amusements. If you're a math/science nerd and you read Gardner at a young age then one of his books probably belongs on your list. Gardner's three articles on Conway's Game of Life are still some of my favourite pieces of science writing - a perfect encapsulation of what I love about brains and games.
Valentino Braitenberg, Vehicles. The chapter called 'Selection, the Impersonal Engineer' is one of the clearest accounts of natural selection I've encountered. Just three pages long, it's a model of concision and elegance - yet it's just a sideshow in this astonishing series of thought experiments demonstrating how 'intelligent' and 'emotional' behaviour can emerge from simple systems utilizing only primitive internal state/representation (or none at all). For a while, half the projects at the MIT Media Lab boiled down to elaborations on Braitenberg's imaginative experiment. I read it as an undergrad working in Bruce Blumberg's Synthetic Characters Group, helping the (mildly terrifying genius) grad student Marc Downie build ethologically-inspired musical creatures. The group was full of artists and weirdos (including Bill Tomlinson, who now does interesting work out at UC Irvine), and Braitenberg's quirky creativity was one of our models. I adore this book.
HONORABLE MENTION: A Thousand Years of Nonlinear History (de Landa), Structure and Interpretation of Computer Programs (Abelson and Sussman), Joyce's Book of the Dark (Bishop), Stiffed (Faludi).