(I get the list in digest format, so I'm replying to more than one thing here!)

To add my $.02 to the recommendation list for Andy Hoffman:
I second the Annie Dillard and Eudora Welty.
Ivan Doig (This House of Sky, Heart Earth, and others).
Maya Angelou.

On the humorist/thinker topic:
Some of today's funny guys studied philosophy in college -- Steve Martin, Jay
Leno, various members of the Monty Python troupe.  (Although I'm not saying that
everybody who studies philosophy is necessarily a "really deep thinker," I think
one certainly does not seriously study philosophy unless (s)he is ready for a
workout.)  I don't consider myself an academic, but I can't watch/listen/read
the Python stuff without realizing some serious thinking has been involved in
their creative process.  Ditto for Martin.

--Gaye C. Auxier
OKC, OK