He wrote the best book ever on the 60s counterculture, "The Electric Koolaid Acid Test," about Ken Kesey, etc. Another book, "The Kandy Kolored Tangerine Flake Streamline Baby," is a priceless and fabulous chronicle of the wonderful car culture of America. As a writer, he's hilarious, and has had me laughing out loud while reading many times. He's just witty and funny and cuts through liberal hypocrisy like no one else.
The neat thing about Tom Wolfe (whose "The Right Stuff" kind of put Chuck Yeager -- the legendary test pilot who broke the sound barrier -- on the map in that it let America know about this hitherto mostly unknown hero) is that although he looks and dresses like a New York City dandy and elitist (I believe he's a Virginian by birth), he absolutly recognizes, understands, and respects people who may not have much in the way of formal education (to put it mildly), culture or polish, but who are extraordinarily intelligent and American.
Tom Wolfe is one of the best chroniclers -- maybe THE best -- of mid to late 20th Century America. I love his work. It's so odd, that he looks and seems as if he would be a super-snob, but the reality is that he's the opposite.
I loved the movie "The Right Stuff" and watch it several times a year, but the book is a thousand times better. For me, the book motivated me to read both of Yeager's autobiographies (yes, he wrote two! "Yeager" and "Press On"), Gordon Cooper's autobio "Leap of Faith," and a few other books about space whose titles escape me. I also read Lovell's book on Apollo 13.
Two of my favorite quotes from Yeager:
"I've always said that the rules are made for people who aren't willing to make up their own."
And ...
"My legacy, I suppose, is speed. But looking back, I don't think many people save a lot of time by moving faster from one point to the next, because from the time you're born until the time you die, it's pretty cut and dried. You have to take advantage of time, not speed."
You should also add “Man In Full” as essential reading from the Tom Wolfe catalog. That is probably my favorite Wolfe book. I especially like the “workout session” that the in-over-his-head tycoon gets put through by the bank and the part where the hard-luck kid who loses his job in the frozen food plant tries to get a job as a typist in the city, ends up getting his car towed and gets harangued by his wife and mother-in-law when he calls them on his last dime looking for some money.
A book you might enjoy, about another major player from that era and especially beyond, is Boyd: The Fighter Pilot Who Changed the Art of War.
Check out his Wiki entry.
http://en.wikipedia.org/wiki/John_Boyd_%28military_strategist%29