Word on the Street: Debunking the Myth of a "Pure" Standard English - John McWhorter
This book will make you stop and think twice about what you're saying, why your language has adapted the way it has, and the image you produce by the words you arrange. True, it is kind of a nerdy English-y book, but after taking a basic Linguistics course, this type of English Philosophy appeals to me.
On Love - Alain De Botton
Contrary to title, this book isn't a romance novel (well, at least not in the ordinary sense). This is a philosophical view of courtship, relationship, and ultimately, breaking up. From detailing the odds that the main character and his later-girlfriend meet, to the significance of her leaving a toothbrush in his bathroom, this will make you think twice about any relationship for the rest of your life. Any of De Botton's books have heavy emphasis on the philosophy of the situation, and are excellent. I have also read Kiss and Tell, and am working through How Proust Can Change Your Life and others.
The Complete Works - E. E. Cummings
While I am a huge 'underappreciated' poetry nerd, Cummings is the all-around reference poet. You can talk about the Xiape and ViVa editions with classmates over coffee, or casually mention a poem in conversation with professors. Cummings' work is universal. I also recommend Eliot, Yeats, and Berryman.
Middlesex: A Novel - Jeffery Eugenides
The Virgin Suicides - Jeffery Eugenides
Both of these are fiction, but guilty pleasures. Eugenides carves his characters into the parts so carefully, and so flawlessly, that you immerse yourself in their lives. The books are also somewhat fact-based; for example, Middlesex has heavy emphasis on Detroit in the twentieth century. I also got to read about the Ambassador Bridge not a day after I was on it (yay Wonderland!).
Zen and the Art of Motorcycle Maintenance - Robert Pirsig
So it's already been mentioned twenty times or so. I read this at sixteen, and at that point, it was the hardest book I had ever suffered through. The first time through, I hated it. Now, I have dog-eared passages I read through frequently. The person who gave this to me wrote in the back that this was a book that should be passed on. I wholeheartedly agree - go buy your own copy and read this, if you haven't already.
more later.