In no particular order, these are a few favourites that are definite keepers on my shelf.
If you’ve read them, you know what I mean. If you haven’t, try to get your hands on at least one. (The links go straight to each author’s site, or as close as I could find.)
Amusing Ourselves to Death
Classic Neil Postman. He’ll have you at the foreword.
The Gutenberg Elegies
This might be the toughest one to find, but a few university sites have PDFs. A little heavier going than Postman, but well worth the time.