Here we go...
In my opinion the best cover that Wired magazine has ever had was on the December 1999 issue. It depicted a winged woman casting herself off of a cliff. I believe it was meant to signify the excitement and potential of the new millennium, but there seemed to me to be a note of unease and uncertainty about the picture. Excitement tinged with a frightening leap of faith into the unknown. Of course the new millennium was just a calendar ticking over from one year to the next, and the importance of it, had only to do with the human brain liking round numbers.