The Winterlong Trilogy by Elizabeth Hand
Gothic, Grand Guignol-drenched post-apocalyptic science-fantasy. "Febrile" is a word that comes to mind – the language is overstuffed, it's dense with references to fantasy and folklore, and the characters are run through the wringer. Not the last of her novels to feature a transmogrified Washington DC as a primary venue.
Waking the Moon by Elizabeth Hand
Roman á clef and supernatural romance (in the traditional, not Twilight sense) featuring the hidden war between the Benandanti, a sect of nasty old patriarchal quasi-Catholics, and the forces of Othiym Lunarsa, goddess of a long-suppressed matriarchal death cult. If Camille Paglia ever read this, she probably loved it, but the central story is basically an overheated, fantastic version of Whit Stillman's Metropolitan and so therefore I love it.
Waking Beauty by Paul Witcover
Witcover was buddies with Hand around the time that this was written, and it betrays a similar set of preoccupations. This book is a super uncomfortable hybrid of Anne Rice's recast fairy tales and The Handmaid's Tale. This book is upsetting, but very good.
The Iron Dragon's Daughter by Michael Swanwick
I can't really improve on the review that I linked to ; I'm sure that whoever wrote it is very smart and handsome. It also pretends to be a fantasy novel, but is actually as ruthlessly rigorous in following its chosen rule set as any hard sf.
Dead Girls by Richard Calder
Hahaha what? I include this mostly as a cap to the previous few, because this is also soaked in excess, although it's not as feminist as any of those, despite largely being about women and social control. It's hard to tell what Calder was going for when he wrote this; it's very tightly written, and has a lot of trenchant, post-cyberpunk things to say about the post-corporate world. It's also filled with sexual violence (although fortunately? not the "character-building" kind; Calder's not exactly a nihilist, but he's not exactly not a nihilist).
Her Smoke Rose Up Forever by James Tiptree, Jr. / James Tiptree Jr.: The Double Life of Alice Sheldon by Julie Philips
Robert Silverberg once told a joke that only became funny much later, when in an introduction to one of James Tiptree, Jr.'s stories in Again, Dangerous Visions (a book that is a pretty rich joke all its own) he described the "ineluctably masculine" voice of the author. Silverberg was being completely serious, which made it all the more embarrassing when it turned out that the ineluctably masculine voice of Tiptree turned out to be the creation of Alice Sheldon, a former socialite and psychological warfare expert who might have been bisexual but was definitely a woman.
It is very hard to say whether Sheldon's writing or biography is more fantastic; "The Women Men Don't See", "The Screwfly Solution", "The Last Flight of Doctor Ain", "Love is the Plan the Plan is Death", and "The Girl Who was Plugged In" are all bona fide classics of screamingly feminist science fiction (there's a reason it's called the Tiptree Award). At the same time, here is a woman who was the first white child to go into the heart of Africa (and who lived her whole life in the intimidating shadow of her Chicago socialite mother, a famous children's book writer); who was a socialite in Berkeley who had a life straight out of a Fitzgerald novel; who learned to read high-altitude surveillance photographs as part of the war effort during World War II; who was involved in the reconstruction of Europe after World War II and participated in the conversion of the OSS into the CIA; who got an advanced degree in psychological warfare; and who at one point said screw it and became a professional chicken farmer – all before starting her career as a science fiction writer, which she did secretly and well enough that it was a genuine scandal when she was outed as a woman.
Tiptree was never able to make the jump to novels (I mean, she wrote four or five, and I've struggled through them – they're entertainingly doom-filled but schematic, and her characters aren't built for long narratives), and after she was outed she lost her voice and her mojo (her late stories are basically either clumsy garbage or inarticulate screams of rage), but the stories she wrote in the high period of the mid- to late-70s are hammer blows one and all. Tiptree was as important to my personal development as Chip Delany (see below), but not nearly as kind. Her biography didn't come out until a few years ago, and I both devoured it and was deeply saddened by it; it is in its own way a profoundly feminist document, because it clearly and empathetically shows how and why Sheldon's life was as troubled and frustrating as it was.
The Dispossessed: An Ambiguous Utopia by Ursula K LeGuin
I love Ursula LeGuin (she's probably the most famous writer from Portland), and I love this book. It would be so easy to be cynical about it and paint it as leftist claptrap. It would be easy to bag on LeGuin, who was also the privileged daughter of famous people (her father is as significant an anthropologist as Claude Levi-Strauss (and also his contemporary), without much of Levi-Strauss's colonialist baggage) and who was fairly late to the feminism party. But you'd have to engage in a pretty wrongheaded reading of American and feminist history to do so; LeGuin was pushing science fiction into places a lot of its practitioners didn't want it to go, and she came to feminism honestly, as an adult, and engaged with it with a thoughtfulness that was as rare during the Second Wave as it is today.
The Dispossessed is basically a tale of two worlds and the tense relationship between them; one is a capitalist, militarist world much like our own, and the other is a peaceful, anarchistic communal intentional community settled by people who bailed on the first. As the title suggests, nothing is exactly what it seems, and even with all of the ambiguity that LeGuin worked into the novel, it is filled with baggage and unexamined assumptions. It is deeply problematic, is what I'm saying, which is why the next book on the list end up mimicking its title (that book tries to unpack much of this one's more problematic aspects, to varying degrees of success). Even so, its positive portrayal of a communal, anarchistic society, and the seriousness with which it explored its themes of reconciliation and forgiveness, make it a pretty singular work in the history of sf.
Trouble on Triton: An Ambiguous Heterotopia by Samuel R Delany
This book is still years ahead of where we are now; it has more to say about privacy, gender, sexuality, and people's basic inability to come to terms with themselves than most other authors' entire ouevres, regardless of genre. It's really easy to think that Delany is mocking the book's protagonist, but I think, having read it a few times, he's up to something much more humanistic and empathetic than that. Dude meets lady, dude falls in something with lady, dude becomes lady, lady ends up being unsatisfied with being a lady, lady ends up realizing way too late that she actually had no idea what she wanted in the first place. Meanwhile, the solar system is engaged in a cold war turning hot, and most of the nation states in the book are run by authoritarian, self-interested assholes, which is of course entirely fictional.
Dhalgren by Samuel R Delany
This is a capital-n Novel, one of the finest of the entire 1970s, and one of the books most important to my own personal development. I don't know whether it's fantasy, urban magical realism, or a particular kind of speculative fiction that sort of disappeared in the mid-1970s and resurfaced in the mid-1990s as "slipstream". Aside from his pornography, it is the most ineluctably Delany novel he wrote: a tale of an amnesiac(?) drifter who comes to a destroyed city, befriends some people, has sex with some people, is exploited by some people, witnesses much human drama, and then disappears into his own journals before ending the narrative where it began. Delany wrote this in response to the Watts riots and white flight, but it's as much a transmutation into fiction of his own experiences as a bisexual / gay black man experimenting with many different styles of living in a changing society.
Stars in My Pocket Like Grains of Sand by Samuel R Delany
Probably the widest-screen science fiction that Delany ever wrote, while at the same time being among the most intensely observed. Also just completely gay on every possible level; the games he plays with pronouns ("she" is used as a marker of sexual desire rather than a straightforward marker of gender) and the way people relate to each other is more or less inextricable in my head from what I know of his biography and seems very much of a piece with the codes and morés of late-70s / early-80s gay New York. Ends abruptly; many forlorn fans have been waiting in vain for the sequel ever since, but Delany has said on various occasions that AIDS pretty much destroyed his ability to finish the sequel by destroying the milieu that its fictional world was based on.
Steel Beach by John Varley
Varley is a slippery fish; he writes great short fiction, and he was kind of a cornerstone of 1970s science fiction, when it was going through kind of a rough patch, but his novels are very hit or miss and it's hard to avoid the sense that he only occasionally lives up to his potential. Steel Beach is probably my favorite novel of his; it exists in dialog with much of classic SF, and builds on some of the themes in Trouble on Triton, most notably the idea of a world where changing your sex is straightforward and unremarkable. 20 years on from its original publish date, it's more interesting in what it gets wrong than what it gets right, but Varley is best when his characters are put through some kind of psychological crisis, and the protagonist of this novel is in even worse shape than the protagonist of Triton. If you want to check out his short fiction, "Air Raid" (which was turned into the much inferior novel Millennium) and "PRESS ENTER" are worth searching out.
Stations of the Tide by Micheal Swanwick
This is a curve ball I like to toss at fans of cyberpunk; on the surface this is futuristic space opera with a science-fantasy tinge to it, along the lines of Alistair Reynolds or maybe even Iain M Banks, but this is set in the same universe as his earlier novel Vacuum Flowers, and shares with Steel Beach the idea of a humanity tossed off its homeworld and forced to fend for itself elsewhere. What's most interesting about Stations of the Tide, aside from its extremely enigmatic protagonist, is why humanity can't go home again: Earth is the site of a post-singularity group consciousness that is more than human and up to its own enigmatic end (Varley just presumes that aliens are pissed at how we treated the whales and booted us off the planet wholesale).
If you like this, you should probably read some Gene Wolfe, but he's a whole other thing that I'm not going to get into right now.
Ancillary Justice by Ann Leckie
This book is in the process of winning all the awards. It deserves them, too, because it tackles head-on a whole bunch of interesting, complicated ideas about governance, compulsion, and responsibility. It also plays fun games with pronouns, although in a less loaded way than Delany. Since the book turns on the protagonist's story, I won't say much more, but I will say that I'm looking forward to the sequel, which is slated to be published late this fall.
Ghost in the Shell 2: Man-Machine Interface by Masamune Shirow
Because this is a manga, because this is part of the sprawling GitS franchise, and because of Masamune's predilection for improbable boobs and "lesbian" sex, people tend to look askance at me when I recommend this book, but it is hands down one of my favorite attempts to really grapple with the consequences of cyberpunk's implicit equivalence of machine and human intelligence. Because it's a graphic novel, it can get away with narrative tricks that would be difficult or impossible in prose, and because Masamune is a bona fide obsessive mutant, it has a density and complexity that would not tranlate at all well to anime. It's "about" the quest for a Macguffin, but the interesting part is watching the way that the various versions of The Major (one of the greatest characters in the history of Japanese pop culture) interact with each other and the post-national police states that are what remains of the world.
Appleseed by John Clute
Where Man-Machine Interface is soaked in post-human philosophy, Appleseed is soaked in genre. John Clute literally wrote the book on science fiction, and is mostly known for his (again literally) encyclopedic work documenting the history and nature of the genre, as well as his (excellent, incisive, sometimes entirely too erudite) criticism. Appleseed is his only foray into fiction, and I think it confused the hell out of most readers. BUT it is a great book, again not so much because of the story, which is basically a WHO CARES space opera plot about some dude who turns out to be more important than he looks, but because of the texture and detail and intertextual density. Borrows ideas from most of the books on this list older than it (the notion of societies collapsing due to fugue from Stars in My Pocket Like Grains of Sand, the harlequinade from Stations of the Tide among many others, etc) as well as most other quality sf period. Culminates in a dazzling, hyperbolic, satirical take on America's self-celebratory greatness (Clute is Anglo-Canadian), and maybe the whole book is an elaborate joke. I don't care; I love it and I love what Clute does with language in it.
Lilith's Brood by Octavia Butler
Speaking of responsibility, compulsion, and survival, this trilogy that combines the aftermath of a global nuclear war with First Contact is a sometimes brutally uncomfortable and confrontational take on what would happen if outsiders showed up to save us from ourselves. There are aallll kinds of echoes of post-colonialism, feminism, and racial politics in here, but it's nothing so simple as allegory. I know I make some of these books sound like chores to read, but even the most challenging books in here have a lot of exhilirating moments, and the sense of genuine possibility – of becoming more than we are by becoming other – in this series makes it no different.
The Malazan Book of the Fallen by Steven Erikson
This is something completely different. A 10-novel military fantasy series written by a professional anthropologist and archaeologist, based on a roleplaying campaign he and several friends have been working on for over 20 years. Erikson is a talented writer who loves story and plot (and, occasionally, character), but he was still figuring things out when he wrote Gardens of the Moon, the first novel, and as a result, while it's an absolutely essential, in media res introduction to the series (by which I mean you're going to be referring back to the events in the first book even when you're halfway through the tenth volume), it's also sort of a mess. Unfortunately, these novels are all incredibly long, and you have to read about the first three before you can make up your mind whether it's worth it to read the next 7. He also continues introducing major characters throughout the series, and keeping track of everybody becomes a major challenge, especially because, unlike GRR Martin, he's not so fond of garbage-collecting the character list.
My personal opinion is that Erikson took the skeleton provided by Glen Cook's fun but sometimes silly Black Company novels and made them do interesting work by grounding them in his anthropological preoccupations. These books are dark (occasionally and increasingly grimdark as the series progresses), and the overall story is Tolkienesque in its grandeur (although not at all Tolkienesque in its language – Erikson's characters crack wise and fart and engage in casual grabassery that would be deeply alien to Tolkien), and they inhabit an universe of moral ambiguity and ethical compromise; there are characters you come to know and love who have devastating secrets that reveal them as monsters, and there are characters who seem like irredeemable assholes who turn out to have very good reasons for being crabby, vindictive jerks.
Erikson also earns the distinction of being one of the few authors who can guide a story of this scope and ambition to a satisfactory resolution. The last few novels sag in parts under the weight of all of the significance he's piled onto the story and the fated nature of many of the characters; there are some significant loose ends; and I still am unsure what exactly he meant by the ending. But still, he landed it, and it seems like the ending he reached was the ending he planned. Good job!
This Time of Darkness by HM Hoover
Another curveball – this is the young adult dystopia I was talking about when we discussed the Hunger Games and Divergent. This story has been told a million times, and I'm not sure it would resonate with me so much if I hadn't read it originally at an impressionable age, but Hoover writes with a quiet assurance that I find deeply comforting even as an adult. A boy and girl live in a grimy, broken-down authoritarian society deep underground in the wake of an unspecified apocalypse. They figure out that there is more to the world than the propaganda and dysfunctionally regimented society in which they've been raised, and they light out for the territories. Hoover rings interesting changes on what were even at the time pretty familiar tropes, and expands on this somewhat in a subsequent novel, Orvis, which is a pleasantly lackadasical coming of age novel with lots of echoes of Heinlein's juveniles.