I think Ham on Rye by Charles Bukowski. That and his book Post Office. Just the first things to come to mind, even though I can't remember them and need to read them again.
Books
The Red by Tiffany Reisz
A beautiful young artist submits to a rich, sexy, kinky man for a year to save her gallery. Very hot, strange book. Really good though.
Model land by Tyra Banks. Delightfully nutso buttso. I wish there was a sequel
Kafka On The Shore by Haruki Murakami.
All of his books are a little odd but this one is truly baffling. Compelling story told using beautiful language and I kinda love it but I don’t understand it at all. I spent a few years post-read encouraging others in my circle to read it as well so we could “WTF?!?” at each other about it.
Walkers (Graham Masterton)
It (Stephen King)
Insomnia (Stephen King)
Several by Dean Koontz
I can't even recall all of the crazy plots "Tick Tock", Sole Survivor, 77Shodow Street come to mind.
Gnomon, by Nick Harkaway, is great and crazy.
Honorable Mention must go to Naked Lunch, because it was so impenetrable that I gave up a couple pages in, so I have never read it.
Private Parts by Howard Stern. That book had some of the craziest stories in it. I laughed my ass off several times while reading it. Even if you've never heard of Howard Stern, it's worth the read.
There’s a short novel called I Who Have Never Known Men by Jacqueline Harpman. It’s a bleak dystopian future story that was unique.
Paradise Rot by Jenny Hval was like reading the thoughts of a deranged college student who is trying to figure out her sexuality.
Jawbone by Monica Ojeda is a slow burn of a psychological horror. It was so out there but it was so good.
I love weird books.
Valis by Philip K Dick
Ubik by Philip K Dick
Flow my Tears, The Policeman Said by Philip K Dick
Dr.Bloodmoney by Philip K Dick
Despite being one of my favorites, 100 Years of Solitude is pretty crazy
Probably The Wasp Factory.
After I finished I thought "What the hell did I just read?"
Dead Astronauts by Jeff Vandermeer
The Long Walk by Steven King, absolutely blew me away.
I thought Eyes of the Overworld and Cugels Saga by Jack Vance were the most wild shit I’ve ever read, then I read his Rhialto the Marvelous. The situations are so absurd and the dramatic irony so funny.
The Dark Tower series by Steven King.
I think it felt crazy mostly because you had no clue what the fuck was going on. There wasn't really an explanation of the world or what was happening. You just kept hearing "The world has moved on." You go to some pretty whack places with pretty whack people, and at least in the first book, you get no explanation of why things are the way they are.
Ultimately, I got a few chapters into the second book and just gave up. I got annoyed feeling confused and not knowing what was going on or where I was. And the whole "lone cowboy on a mission" didn't really vibe with me either.
Interzone Incorporated by Adam Ireland.
Makes its inspiration, Naked Lunch, seem sane and family friendly.
Junkie
Acting Class by Nick Drnaso.
His books are all… uncomfortable, but this one even more so. It’s like the uncanny valley in a story. If you like graphic novels and weird stuff, he might be your guy.
On concept alone: Light From Uncommon Stars by Ryka Aoki
On actual writing/the journey: Number 9 Dream by David Mitchell
Bury My Heart at Wounded Knee.
Anything by Carlton mellick III
Super fun quick reads
Invisible Monsters by Chuck Palahniuk. It left me in quite the state of mind after I had finished it. It really wasn't the relaxing afternoon read I had hoped it was.
The Raw Shark Texts by Stephen Hall.
I’ve never seen anyone talk about this book. Read it in the Dutch translation as a teen and it stuck with me for years. Never read the English, so can’t vouch for the original but wacky is a good word
It dives into linguistic theory, extremely meta concepts about words and reading and language and it absolutely blew my mind back then. Maybe I should revisit to see what it’s like now
I LOVED "Blood and Guts in High School" by Kathy Acker
The Illuminatus! Trilogy by Robert Shea and Robert Anton Wilson. It was kinda a tough read for me when I read it as a teenager because it goes back and forth between a few different stories happening at the same time, I should give it another read now since my reading skills improved since half my life ago