I just used to call House of Leaves a ‘clusterfuck of literary devices,’ but “satire of academic criticism” is equally accurate, and much more conversational– I guess.

Besides House of Leaves, the only other book on this list I’ve read is A Scanner Darkly. The narrative really made me feel like I was in the throes of a trip, perhaps stumbling about. Good stuff.

Another book that’s part of this cult of trippy-ness– though perhaps not of a quality to merit inclusion in this list– is Go Ask Alice. It’s an epistolary novel I read in middle school (of all times) that chronicles the titular Alice’s rise from and repeated declines into full-on drug abuse. The character’s two contrasting states of mind really made me feel the differences in reality of one who is at times sober, and at other times decidedly not.

The Master and Margarita – Mikhail Bulgakov

Brilliant.

Vurt, Nymphomation, Pollen and Automated Alice by Jeff Noon.
Virtual reality ‘trips’ induced via sucking on programmed feathers, dominos as a lottery type game and cross breeding of people, dogs and shadow-people. Yeah, trippy is an understatement!

A very good list, but I feel compelled to add at least The Stone Junction by Jim Dodge (I worship this book) and The End of Mr Y by Scarlett Thomas.

The Man Who Was Thursday, by G.K. Chesterton……

The Crying of Lot 49

A shoutout for the AUDIO version of Naked Lunch — since BEAT prose was meant to be read aloud — creating the full trippy experience … AWESOME

cormac mccarthy’s blood meridian.. i am afraid to reread this wild troubling tome.
“It was a lone tree burning on the desert. A heraldic tree that the passing storm had left afire. The solitary pilgrim drawn up before it had traveled far to be here and he knelt in the hot sand and held his numbed hands out while all about in that circle attended companies of lesser auxiliaries routed forth into the inordinate day, small owls that crouched silently and stood from foot to foot and tarantulas and solpugas and vinegarroons and the vicious mygale spiders and beaded lizards with mouths black as a chowdog’s, deadly to man, and the little desert basilisks that jet blood from their eyes and the small sandvipers like seemly gods, silent and the same, in Jeda, in Babylon. A constellation of ignited eyes that edged the ring of light all bound in a precarious truce before this torch whose brightness had set back the stars in their sockets.”

I second ‘Vurt’ and would also suggest ‘Accelerando’ by Charles Stross, and ‘Excession’ by Iain M Banks

I seriously can’t believe that Steven Hall’s “The Raw Shark Texts” is not included in this list. It is the fantastic, appropriately “heady” (more so than most things I’ve seen published in several decades whilst still managing to be accessible)…

If you want something mind bendy, a little dark (but optimistically so) at times… check it out.

Quake by Rudolph Wurlitzer

How bout Steppenwolf by Herman Hesse

Trippy!

I’d add The Keys of Enoch by J.J. Hurtak. Truly mind-expanding. Just a plate of shrimp (h/t to Tracy Walter in Repo Man): Yesterday, late afternoon, I started reciting Tweedledee and Tweedledum’s poem. I had no idea it was Lewis Carroll’s birthday.

Jesus’ Son, Denis Johnson

One of the trippiest of all: The Teachings of Don Juan by Carlos Casteneda…actually the whole series is extremely trippy. And no list of trippy would be complete without Huxley…

Totally agree with David, Steppenwolf was the second thing that came to mind when I saw the title of the article. My favourite book is also the most trippy I’ve ever read, The Third Policeman by Flann O’Brien, but possibly more due to delirium tremens rather than lsd.

The Book of the New Sun by Gene Wolfe is one of the most rewarding bizarre books I have ever read. I spent the better part of the 90s reading Phillip Dick (even wrote my masters thesis on him) but I found something even more with Gene Wolfe. While PKD wrote about what was to come when artifice and nature become indistinguishable, Gene Wolfe starts miles and miles beyond.

I was hoping to see “At Swim-Two-Birds” on this list, by the great underrated Irish writer Flann O’Brien (the pen name for Brian O’Nolan).

It’s a @#$%ing hilarious first-person narrative about a student writing his first (abjectly poor and melodramatic) novel, which is actually three novels that end up weaving in and out of each other. The sub-novels also have subordinate narratives of their own (bad cowboy novels, bad epic poems, etc), so you end up getting a Russian-doll effect as characters pop in and out of the wrong stories and interfere with the plots of each other’s stories. The overall novel is framed by the author’s picaresque description of the his days (and semi-alcoholic nights) as a college undergrad in Dublin.

It’s beautifully written – even his sub-novels are breathtakingly bad in a beautiful way – and the dialogue is funny and rich in the tradition of the great Irish writers.

It’s like Joyce crossed with Pynchon with Cervantes. Read it!

I can’t believe I didn’t think of those also– The End of Mr. Y, The Raw Shark Texts, and At Swim Two Birds! I agree!

Anna Kavan’s hallucenogenic novels (as distinct from her Virginia Wolfe-esque pieces, before she got on the heroin for real) are pretty good too. Mercury, and Ice, I believe are the two.

Gulliver’s Travels by Jonathan Swift

Anything by Charles Stross, and check out “don’t bite the sun” by Tannith Lee. Thanks for the Repo Man quote!

Having read Alice in Wonderland as a child, I object to it being considered as an appropriate book for children. It really freaked me out before I was mature enough to understand why. It is one of a rather long list of books, movies etc. that adults seem to think are “for children” but are in fact NOT!

In a quick scan of the comments, I was shocked not to see Wolfe’s “Electric Kool-Aid Acid Test”. Forgive me if I overlooked that comment.

In the Night Kitchen, by Maurice Sendak.

Amos Tutuola’s “The Palm Wine Drinkard” is both an adventure story through a landscape of magic, ghosts, and monsters and an adventure to read as his syntactical quirks and spiraling/tangential storytelling run circles around the reader’s attempts to impose a narrative order. One has to just give in and be carried along.

“Vurt” by Jeff Noon and “Coma” by Alex Garland. Irvine Welsh’s “Ecstasy” is also pretty trippy.

Carroll’s Hunting of the Snark is much tripper than any of the Alice books, by a factor of 42, as even Douglas Adams would admit. And I’d also nominate Raymond Roussel’s Locus Solus as being so trippy that it just might blow your little minds … yow!

Ditto Flann O’Brien, Thomas Pynchon, and G. K. Chesterton.
And believe it or not, Naked Lunch was written before Burroughs had struck upon the idea of cut-ups.

“Fear and Loathing in Las Vegas” by Hunter S. Thompson is not a novel. It’s nonfiction, gonzo journalism. It was considered by many to be one of the hallmarks of “the New Journalism,” and later, literary journalism.

Also, I would recommend “Tristram Shandy” by Laurence Sterne as one of the trippiest books of all time, even though it was published eons ago, in 1759-1767.

Definitely need to add Haruki Murakami’s “Hard Boiled Wonderland and the End of the World” to your list….

In Watermelon Sugar, maybe?

What about Tom Wolfe’s Electric Kool-Aid Acid Test? Primarily for the Merry Pranksters scene where they spike the Hells Angels punch with lots of blotters. :-)

Oh and Carlos Castaneda’s- Separate Reality…

I simply cannot wait to read The Orange Eats Creeps!

Superpostapocalypticexpialidocious by John Riley (if I do say so myself) is a collection of twisted Twilight Zonesque psychedelia.
Try “Else Fine” or “The Parrot’s Tale” for earlier trips.

Kappa, by Akutagawa, or Woman in the Dunes (or anything by Kobo Abe).

Neverwhere by Neil Gaiman, and I vote for Electric Kool Aid Acid Trip too.

This is a pretty good list…having not read all of them. I missed seeing any Kurt Vonnegut, even Slaughterhouse Five…and Robert Heinlein’s Stranger in a Strange Land was one of my favorites.

No one said Roald Dalh, books like Georges Marvellous Medicine… Beside that I would also say Jacques Yonnet with his Paris Noir: The Secret History of a City.

Barefoot in the Head, by Brian Aldiss. The story of the aftermath of a war fought with psychedelic aerosols.

A Clockwork Orange.

“See, kids: why take drugs when you can just read these crazy books?” So no chocolate? No tea? No coffee? No aspirin? You don’t take any of these?

One of my favorite trippiest books is Filth by Irvine Welsh.
You’re never really sure who’s who BEFORE the guy’s tapeworm covers the text, visually, then slowly takes over the narrative and explains what the heck’s going on. Check it out, and I’ll get me a new copy! ^_^

OH! And of course The Illuminatus! Trilogy. That shit is a trip! …and a little bit of hard work. *_*

I would say The New Life by Orhan Pamuk. The protagonist starts reading a book that takes his life to an unexpected turn. And after a point, that fictitious book becomes one with the actual book you are reading. (I wouldn’t want to spoil it so I wouldn’t explain it more clearly)

I’m with Andy… gotta add the Illuminatus Trilogy by Robert Shea and Robert Anton Wilson. Most of Wilson’s non-fiction is pretty trippy too.

Godel, Escher and Bach, by Douglas Hoffstader…

And also, Jitterbug Perfume, by Tom Robbins.