Reddit mentions of Storming the Reality Studio: A Casebook of Cyberpunk & Postmodern Science Fiction

Serial Experiments Lain should get touched on as both one of the more abstract/intellectual cyberpunk works and a rare example in the genre of a story driven by a non-sexualized, non-action-girl female protagonist. It also manages to avoid almost every cliche, so it'd be an interesting counterpoint to those who feel cyberpunk is just gritty future noir in rainy urban centers where everyone has robot legs.

I'm rereading Bruce Sterling's "Schismatrix" right now, and his story "Twenty Evocations" would be great to throw into a class like this. It's short, it's poignant, it's literary and someone already put together a great list of questions to ask a class after reading it.

Tad Williams' "Otherland" series is way too long to cram into a class like this, but may deserve a mention for being one of the more diverse and human works in the genre. It features characters from a wild variety of backgrounds, and manages to pull off the "global cultural melting pot" that so many cyberpunk works aim for remarkably well.

Greg Egan's "Permutation City" has some really wonderful questions about persistence of identity, time and relativity, subjective experience and physical reality, but it's still melting my brain too much to even know how to summarize. Ditto "Aeon Flux," which is at least shorter. Episodes like "The Purge" are framed around some great open questions on morality, free choice and such. I can't imagine you could get away with showing it to a high school class, though; and I took AP classes where half this crap was part of our reading when I was in high school.

I feel Peter Watts and Paolo Bacigalupi do "modern" cyberpunk well, adapting the genre's themes to contemporary concerns and technologies. Semi-relatedly, I really wish there were more works in the genre that address social and/or political issues. Kim Stanley Robinson's "New York 2140" might or might not qualify.

There's also Storming the Reality Studio, a fantastic anthology which is heavy on early cyberpunk, protocyberpunk and genre influences and nonfiction by Kathy Acker, William Burroughs, John Shirley et al.

Also Hackers. Shut up. You know it's awesome.