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I would recommend:
Both collections of essays by David Foster Wallace, Consider the Lobster and A Supposedly Fun Thing I'll Never Do Again. His writing is challenging but funny, entertaining and touches on some fundamental truths.
The Medium is the Massage by Marshall McLuhan. This stretches the limits of the book form, both visually and intellectually.
I also liked Nothing to Envy and another Granta book, How to Talk About Book's You Haven't Read by Pierre Bayard.
All pretty full on reads, but well worth the mental effort.
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