Diana put me up to this without meaning to. Making the list was more difficult than I thought it would be, and it’s disappointing that I didn’t have space for Neil Gaiman, Larry McMurtry, Elmore Leonard, or any classic “low fantasy.”
The Return of the King – Choosing which volume to include was the most difficult part of this list. The Two Towers is my favorite; but I included this one because the six chapters that deal with the seige of Gondor and “The Scouring of the Shire” are, in my opinion, the finest pieces of storytelling Tolkien ever produced.
The Silmarillion – I thought long and hard about including two from the same author, but this really has to be here. This is the book that taught me to love mythmaking and worldbuilding; and it adds so much depth to the LOTR trilogy that I consider it an essential fantasy text.
Long John Silver: The True and Eventful History of My Life of Liberty and Adventure as a Gentleman of Fortune and Enemy of Mankind – Bjorn Larssen. A fictional autobiography of Long John Silver. It is possibly the best pirate story I have ever read; it certainly has the best subtitle. Originally published in Swedish and translated by Tom Geddes.
Feet of Clay – Terry Pratchett. This is my favorite Pratchett novel, because it is set in a city in which every type of fantasy creature you can imagine has civil rights, but Golems do not because they are viewed as unthinking automata – only it turns out that the Golems can think and feel. Also notable for its deconstruction of machine politics.
Illuminatus! — Robert Shea and Robert Anton Wilson. An absurdist story that starts out as a murder mystery and devolves into total conspiracy-theory weirdness. Among other things, it includes A Black Mass, a Nemo-esque character with a submarine large enough to transport his Bugatti, an intelligent sea monster, and an army of Nazi zombies. Oh, and sex. Lots and lots of sex. It is the earliest piece of fiction I’ve encountered that states “whomever controls the medium of communication controls society.” It’s worth the read just for that, if you can find a copy.
At Swim Two Birds – Flann O’Brien. I read this one in college; I think it is the first piece of metafiction I ever read. One of the characters is a Pookah, and it has the best last line I’ve ever read. (“Goodbye, goodbye, goodbye.”)
For Whom the Bell Tolls – Hemingway. The first Hemingway novel I ever read and, in my mind, the best. The flashback chapter in which Andres reflects on his bull-baiting career is one of the most exquisite pieces of prose I have ever encountered.
Wise Blood – Flannery O’Connor. Possibly my favorite novel, period. I can’t think of a writer that does dark, low comedy better than O’Connor. The psychology of the protagonist and the religious themes are quite unsettling. Just in general, it is a very disturbing piece of art.
Homage to Catalonia – George Orwell. It reads like a novel, but it’s actually a memoir of his experiences in the Spanish Civil War.
The Collected Works of Billy the Kid – Michael Ondaatje. A series of poems that includes everything from descriptions of photographs to fictional monologues to writing lifted from period newspapers, loosely organized into a long narrative poem about William Bonney, his friends, and associates.