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My favorite DFW essay of all time is this one: http://harpers.org/wp-content/uploads/2008/09/HarpersMagazin...

(and previous discussion: https://news.ycombinator.com/item?id=6694749)

i remember reading that one in "Supposedly Fun Thing I'll Never Do Again", and indeed it is awesome. My favorite is from the same volume, and i can't remember the name but it's about a day spent at a State Fair with an old (female) friend who he refers to as "Native Companion"--so excellent that for a while after reading it i wanted to become a carnie.