1. How to Win Friends and Influence People by Dale Carnegie
    The classic. Drills major points into your head.
  2. The Playboy Interview: John Lennon and Yoko Ono
    This book was in my house as a kid, and I read it constantly. The way John Lennon talked made integrity cool to me.
  3. What Is Your Dangerous Idea? edited by John Brockman
    An incredibly thought provoking anthology of 1-3 page essays by great thinkers on ideas that they think have great danger to them, and could be exploited for bad purposes.
  4. Seven Experiments That Could Change the World
    I'm very pro-science and anti-superstition, and this is a book that defends the possibility of extra-rational activity by examining extremely compelling examples of phenomena unexplained by science that the scientific community has a taboo against exploring. A riveting book filled with cool things. The best chapter is on the mystery of pigeon homing instincts.
  5. The Oxford Book of Aphorisms
    This is a quotation book. Just about every single one is both wise and rock star cool. Heavily represented: Pascal, Voltaire, and others who said great things that are cool to quote and think about.
  6. Do the Movies Have a Future? by David Denby
    The New Yorker film critic traces how film used to be a relevant "national theater," how that ended, and what it would take to be that again.
  7. On Beauty and Being Just by Elaine Scarry
    Beautiful, brief, provocative treatise by Harvard professor Elaine Scarry