Alice’s Adventures in Wonderland , Lewis Caroll
In Lewis Carroll’s masterpiece of nonsense literature, Alice falls through the rabbit hole into an alternate universe where she shrinks and grows (after eating mushrooms and suspect baked goods, no less), where caterpillars smoke hookah, time stands still, and creatures bounce by speaking in riddles. Hallucinatory and wildly colorful, and supposedly all a daydream, it is by far one of the trippiest books of all time.
House of Leaves , Mark Z. Danielewski
Sometimes described as a “satire of academic criticism,” Danielewski’s unconventional, claustrophobic novel forces the reader to work hard to unravel the plot, dealing with multiple narrators, strange text in unusual places, bizarre typography, and copious footnotes. The act of deciphering the novel is itself a disorienting experience, the text an ominous labyrinth that threatens to trap you inside forever.
The Orange Eats Creeps , Grace Krilanovich
This rather terrifying book, about a gang of “slutty teenage hobo vampire junkies” on the hunt for blood and cough syrup in the Pacific Northwest of the ’90s, reads like a drug-induced stream-of-consciousness nightmare, the reader just barely clinging along for the ride. The prose is spastic to the core, a fever dream of thick, dirty slang and sweaty desperation. It’s enough to keep you off the cough syrup for life.
Naked Lunch , William S. Burroughs
Shifting wildly in time and space at what seems like every opportunity, the drug-filled chapters in Burroughs’ novel are meant to be read in any order. Burroughs’ famous “cut-up” technique was meant to mirror the spastic, jangly workings of a junkie’s mind, and in this book, the mania of addiction becomes an actual alternate universe. Watch your step.
Remainder , Tom McCarthy
Less flashy and aquamarine than some of the other books on this list, McCarthy’s first novel is its own kind of trippy. After an accident, a man is awarded an enormous sum of money. Plagued by a persistent and very specific vision of an apartment building and the people within, he uses his new fortune to buy a building, have it changed to the specifications of his vision, and hire actors to re-enact all the comings and goings of his imagined neighbors. The whole thing, as you might suspect, gets very weird very fast.
The Lorax , Dr. Seuss
Really, is there any writer more trippy than Dr. Seuss? Ten of his books could populate this list and we’d be just fine with that. But we had to choose, and something about those Truffula Trees — or maybe all the ahem, college environmentalists we’ve seen wearing The Lorax t-shirts — makes this one the weirdest in our minds.
Fear and Loathing in Las Vegas , Hunter S. Thompson
Ah, how could we leave off the best trip of them all (both literally and figuratively, of course)? Thompson’s hallucinogenic, ecstatic novel, touted as the “best book on the dope decade” by The New York Times Book Review, is full of delusions and indulgences, insanity and nightmares, all fueled by the “two bags of grass, seventy-five pellets of mescaline, five sheets of high-powered blotter acid, a salt shaker half-full of cocaine and a whole galaxy of multicolored uppers, downers, screamers, laughers…. A quart of tequila, a quart of rum, a case of Budweiser, a pint of raw ether and two dozen amyls.” Yikes.
The Metamorphosis , Franz Kafka
What could be trippier than waking up as an enormous insect? Well, maybe playing the violin for an enormous insect who desperately loves you, but the jury’s still out on that one.
The Hitchhiker’s Guide to the Galaxy series, Douglas Adams
Though lots of weird things happen in these novels, we can’t help but think particularly of the Infinite Improbability Drive, whose side effects include Arthur’s limbs slowly detaching, Ford turning into a penguin (briefly), and “an infinite number of monkeys.”
A Scanner Darkly , Philip K. Dick
Another trippy book about the junkies themselves, filled with surreal conversations, blurred faces and reality-melting drug trips, what makes this novel even wilder is that it is supposedly a vaguely fictionalized version of reality. At least, Dick once said in an interview, “Everything in A Scanner Darkly I actually saw.”