So you've snapped up Michael Chabon's Nebula Award winning novel The Yiddish Policeman's Union, and now you want more thoughtful alternate histories to fill your brain and bookshelf. While there are literally hundreds of alternate histories out there (many of them written by various Michael Moorcocks and Harry Turtledoves in different timelines), a few standouts will help you get into the genre and lead you down the happy path to historical mindfuckery. Check out our our suggestions for some brilliant alternate history reading.
A classic of the genre is Philip K. Dick's Man in the High Castle, an early-1960s novel about what happens to the United States after Japan and Germany win World War II. The West Coast has gone Japanese, while the South is full of Germans and the Midwest is still its own independent country. Meanwhile, a mysterious "man in the high castle" has written a book about an alternate United States which won World War II. Dick's mind-bending and tragic novel inspired a whole host of "what if the Nazis won" novels, including the critically-acclaimed Fatherland. Vladimir Nabokov also picked up on the idea of an alternate history novel-within-an alternate history novel for his book Ada or Ardor, about what would have happened if the U.S. had been colonized by Czarist Russia.
Another great look at an alternate United States comes in Philip Roth's The Plot Against America, which is about what might have happened if Charles Lindbergh had defeated Franklin Delano Roosevelt for president in the early 1940s, and the country had slid into fascism.
Several British alternate histories focus on the Napoleonic Wars. Susanna Clark's Jonathan Strange & Mr. Norrell takes place in an alternate nineteenth century England where magic is a recognized scholarly pursuit like science. In fact, in Clark's England, one of the nation's medieval kings was a sorcerer, but the applied use of magic has fallen out of favor. The novel's two eponymous protagonists become the first practitioners of magic in England for two centuries, and aid the government in the war. Naomi Novik's popular series beginning with His Majesty's Dragon posits a Napoleonic War fought in part with dragons.
Jacqueline Carey's mammoth Kushiel series is about what would have happened to Europe if Christianity had not become the dominant religion, and instead paganism reigned. One result of this situation, at least in the region we know as France, is that prostitutes are revered like holy royalty. And in Kim Stanley Robinson's novel The Years of Rice and Salt, Christianity's march across Europe is halted due to the Black Plague and Islam becomes the dominant world religion instead.
Even cyberpunk has its alt.histories: The Difference Engine, by William Gibson and Bruce Sterling, kicked off the steampunk craze with its tale of what would have happened if the computer had been invented in the nineteenth century.