Wow! Here is a site that offers a list, the 100 Must Read books for men (or for women who want to understand them). It is a combination of summer reading, reading you should do before you die, ideas for Father's Day, etc.. Titles run from children's books to heavy heavy reading and include Into the Wild, several from Doestoevsky, The Hobbit, Hatchet, Leviathan, and 95 or so MORE.
At that site is also a link to 'Manly Skills' which includes 'How to Give an Impressive Handshake' and 'Every Man Should Carry a Pocketknife' and more.
As a bonus, the comments are entertaining, and offer other book ideas as well. Check it out! And then, check out some books!
The Essential Man's Library