1. What Makes Sammy Run?
  2. The Wolf Of Wall Street
    They'd watch the movie or read the book in prison
  3. The Prince, Machiavelli
    Suggested by @bjnovak
  4. The 48 Laws
    50 Cent is an apostle
  5. The Art Of War, for appearances
  6. The Bible, for appearances
  7. Anything by Ayn Rand
    Weirdos only