It's not easy to pick just five so I am going to kinda cheat.
Lonesome Dove (1985)
Nova by Samuel Delany (1968)
The Book of the New Sun by Gene Wolfe (1980-83)
The Broken Sword by Poul Anderson (1954)
Catch-22 by Joseph Heller

In no particular order:
In Cold Blood by Truman Capote
The Executioner's Song by Norman Mailer
The Hells Angels by Hunter Thompson
The Poisonwood Bible by Barbara Kingsolver
The Electric Kool Aid Acid Test by Tom Wolf
and since I cannot cut it to 5, I am also adding
A Rumor Of War by Phil Caputo.

That's because you are basically illiterate, Juan.

Yah, it's difficult.

I can't even name a top 2.
My password is password.

Yes it is. There are actually
five
books. Calling it a
"trilogy"
is a joke courtesy of Douglas Adams, the author.
MAGA! FAFO! Schrodinger's Cat walks into a bar, and doesn't. Dumbocraps: evil people who celebrate murder.

That's not five.
Chopper: I'm just a bloody normal bloke. A normal bloke who likes a bit of torture

The Hitchhiker's Guide to the Galaxy
trilogy.
MAGA! FAFO! Schrodinger's Cat walks into a bar, and doesn't. Dumbocraps: evil people who celebrate murder.

Any books on minimalism, they’re more important than anything written in the Bible.

I could never make such a restrictive list nor would I want to have to make it
I like Moby dick, Hemingway, the big three political theorists, some of Nietzsche– who I find extremely difficult to particularize–, some hardcore math and physics texts, MAD magazine collected works books, some of PJ O'Rourke books, and a guy I just started to read, Michael Connelly
Now your turn