The first "asshole" in print was Norman Mailer's in "The Naked and the Dead," which appeared in 1948 and channeled the language of World War II servicemen, especially the enlisted men, who needed to express their frustration at the arrogance and ignorance of their military superiors. So "asshole" begins life as a subversive pull down of the high and mighty, but it didn't enter the mainstream until the 1970s.
Geoff Nunberg charts the life of the word to its ubiquitous present when it can be found in the mouths of presidents (George W. Bush called a "New York Times" journalist a "major-league asshole") and pretty much everyone in between. And yet it cannot be reproduced without asterisks in the "New York Times," and even Fox News has broadcast it only once. Over time, the word has acquired a unique definition -- an asshole is not a cad or a rogue or phony, though assholes may be all of these. And because it is a dirty word, a vulgarism that we pretend does not belong to us, it passes by without self-conscious explanation or affect. It's a very pure reflection of our times and collapsing culture precisely because we pay so little attention to it. Until now.