Haven't read the rest of the post yet, but had to answer the questions.

Hunter S. Thompson. Fear and Loathing in Las Vegas.

I have read the book, seen it adapted on stage in Chicago and seen the Bill Murray verison called Where the Buffalo Roam, but not the verison with Johnny Depp and Benicio del Toro. Actually, I got the book at an airport swap desk after seeing the play.

Good choice.