I love Banks but to catch a non-reader I find you need more dialogue (Graham Greene / Elmore Leonard). Steakley once quipped that he wouldn't have written "Armor" if Heinlein could write action.

I don't know what books count as transgressive anymore, but at 17 I was pretty into those. Starting younger with Catcher In The Rye / Ender's Game, SnowCrash, then later with Trainspotting / Fight Club (book) / A Clockwork Orange (book). +1s to Gaiman, Stephenson, Alan Moore.