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Valentin's 8 Trippy Books in Literature

For Those of Us Who Love All Things Weird & Strange

What is a "trippy" book? In this list, there will be titles that could bear an element of surrealism, magical realism and/or venture into uncharted literary territory. Authors here tend to toss out the rules of reality, genre, imagery, syntax, and even linear story-telling to propel their stories into something profound.



Truly ahead of its time, which is funny for a book where there is no sense of time; the title character Orlando lives through the Elizabethan age and beyond the book's ending in 1928. This novel (written in the form of a biography) is a fascinating & at-times magical pursuit for love & desire. Orlando lives for a time as a man and then transitions into womanhood.


Orlando's gender expression becomes more fluid as the story progresses; and there's a great deal of commentary on gender roles--specifically, how the restrictions that society places on both men and women limit our happiness & fulfillment.


Also, Miss Wolf demonstrates she was a queen of shade because the biographer is as much a witty participant of the narrative beyond its shaper; with cheeky lines & commentary that make you put your hand over your mouth and giggle.


This novel is a love letter to nature, and it also has one of the most beautiful openings I've ever read.


The books weaves the narratives of a handful of people who learn how to see the natural world and what their role is in defending nature in a modern society that tends to overlook its importance.


There are moments when Powers writes almost fable-like and mystical; the trees/plants come alive in a way that makes them seem almost sentient and beyond human understanding.



An elderly widow named Vesta is walking in the woods with her dog when she stumbles across a note that reads: "Her name was Magda. Nobody will ever know who killed her. It wasn't me. Here is her dead body."


But there is no dead body next to the note. Vesta becomes obsessed with solving this mystery of Magda's murder, which eventually takes a menacingly dark turn in a way that only Moshfegh could conjure. I won't say more.


You can't have a list of trippy books and not include Murakami. The cinematic novel is infused with surrealism from a character who sleeps for months on end, shifting the ("camera") point of view, to scenes with jarring & mind-boggling imagery. Touching, funny, deep, and trippy!



Yes, you may have your opinions about the movie being confusing but hear me out. The narrative utilizes themes of reincarnation, karma, and choices that have butterfly effects that echo through time to push this massive story forward.


Mitchell weaves narratives that have correlating struggles in completely different time periods; and we see the fruits of these character's choices from the past through eons of time and an ending that is *chef's kiss*.


More than any other book I've ever read, this book masterfully plays with the idea of a soul returning to complete another life cycle to right an injustice or face an adversary. Mitchell has accomplished something profound in Cloud Atlas.



Ada is a young Nigerian woman who was born "with one foot on the other side."


She develops separate selves within her mind, and a traumatic event in college solidifies their presence and power as these other selves begin to take control of her mind as Ada retreats further into herself.


This is a powerful, cerebral, dark, and unsettling novel as we spend the entire book in Ada's head. Freshwater also has a refreshing take on exploring one's gender fluidity even if you don't have all the answers.



The king of magical realism and lyrical prose. This book refuses to be put down until it is finished, and reads like an exhilarating roller coaster, demanding the reader's mind to be fully present. Delightful, whip-smart, witty, and at times taboo--this novel follows three generations of The Buendia family in the magical village of Macondo. The story follows the family as they long for solitude and yet also cannot deny their human need to be loved. There are political commentaries, magical butterflies and flowers, rainstorms that last months on end, ascensions to heaven, and lots more magical realism than any other book I've read.




This book inspired my love for trippy books. Part literary-horror, part [fictional] "documentary", House of Leaves has two storylines in one dazzling 700 page tome; along with (commentary) footnotes, pages of sidebar notes, letters, burnt scraps of paper, scanned images of torn photos, and many pages where the words are placed to form shapes rather than sentences. This novel is challenging, unsettling and yet evocative.


The main storyline is about a young family that moves into a small home on Ash Tree Lane where they discover something is terribly wrong: their house is bigger on the inside than it is on the outside. That may not seem scary at first, but then a hallway of endless darkness appears in their living room, enticing their two small children to wander inside. Documentary photographer Will Navidson is determined to capture the phenomena that is plaguing his family, but this is only the beginning, as they must now face the horrors of a creature and an ever-growing labyrinth behind a closet door made of darkness, and of an unholy growl which threatens to tear through their walls and consume all of them at any moment. The other storyline follows a beatnik young man who by chance inherits his dead neighbor's life work of compiling a narrative from the only surviving records that could piece together what really happened back at Ash Tree Lane, but also depicts his own descent into madness. This is a masterpiece for people that like to read horror that is more haunting than jump-scare, where fear is infused into the reader's mind rather than startling.


What are your favorite "Trippy" books? Leave a comment below!


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