'stiff' is 30s slang for a working class person (as in 'working stiff'). This would be like saying 'he really lucked out!' today - a mixture of admiration and mild jealousy for someone's (possibly unearned) good fortune.
I read about that on Wikipedia. I've never read the book, though. There's just something about text and paper that doesn't agree with my stomach.
http://en.wikipedia.org/wiki/Talk:Why_the_lucky_stiff#Real_n...
Re:_why is no more
by lambdajones on Wednesday August 19, 2009 @09:28PM
(#774228)
it means why is probably in a remote, hidden mountain village in Colorado.
Does anyone know what that means?