Okay, I'll play....
Here are the ten most influential books I can come up with right now off the top of my head:
Carl Sagan, The Dragons of Eden, a book that I read as a teenager that has forever remained in the base of my brain as an affirmation that humans are animals and often (always?) act as such.
Carl Jung, Memories, Dreams, Reflections: this spiritual autobiography gave me, as a very young man, permission to take "spirituality" seriously, even though I think religions are mostly about power and domination.
John Dewey, Art as Experience: taught me that the aesthetic qualities of experience are more important than the cognitive ones, both for education and for life.
David L. Norton, Personal Destinies, the book that convinced me that paying attention to Joe Gauld's concept of "unique potential" was worthy scholarship.
Henry Perkins, An Imperfect Panacea, a history of American education that focuses on the degree to which the core purposes of schools are so often diluted by the demand that they handle other social problems.
Arthur Powell, et al. The Shopping Mall High School, a book in which the authors describe how the educational system really works to influence who "wins" and who doesn't. (I read this book together with Ted Sizer's Horace's Compromise...an equally revealing book that also offers the benefit of pointing toward some solutions to the ways that high schools get away from their core intellectual mission.)
Thomas F. Green et al., Predicting the Behavior of the Educational System, a wonderful analysis of the ways that educational systems can be expected to evolve over time...I believe the principles enunciated there have pretty much proven to hold true in most cases.
Duncan Kennedy, Legal Education and the Reproduction of Hierarchy: A polemic Against the System, a little book that convinced me that my decision to drop out of Harvard Law School wasn't as ignoble as some people thought at the time.
Ian Pears, An Instance of the Finger Post, an amazing historical novel in which the story is told from three different perspectives...leaves one being pretty sure that we have no idea what's really going on much of the time.
John Steinbeck, The Grapes of Wrath, simply the best novel of all time? Has the added benefit of showing in a viscerally resonating way the social forces that create and reinforce poverty.