Originally posted by: DainBramaged
I already have it figured out for you. See if this link works.
Infinite Jest by David Foster Wallace. Everyone should read this beast of a book.
Rum Diary by Hunter Thompson. Everyone should read this story by the master. Perfectly conveys human emotions.
Lemons Never Lie by Richard Stark. Awesome old school pulp fiction story. Couldn't put it down.
The Brothers Karamazov by Fyodor Dostoevsky. Great examination of the human psyche.
The X-Files Season 1 on DVD (Slimset). - Greatest TV show ever. Might as well start with the first season.
The Eagles Greatest Hits, Vol. 1 & Vol 2 - Good summer/fall time crusing music.
Subtotal: $100.41. Perfect.
Edit: If you don't like my suggestions, you should at least seriously consider the first two books.