In the first instance I can think of of a re-virtualization of a game that semi-de-virtualized a virtualized activity, it was only natural that the crazy Finns were responsible for this pop-cultural strange-loop. Suomea has given us a Virtual Air Guitar, that allows the user to rock out simply by wiggling fingers in air and strumming at nothing, all vid-capped and transmagically technologically transmorgifying the absolute crystalline essence of the wannabe spirit into actual music. Someone else's music that is, since musicianship is a fourth dimension beyond the salve of invention.
What struck me as mindboggling is if you were to consider that this Virtual Air Guitar would have been inspired by Guitar Hero, which was inspired out of pity for air guitarists making fools of themselves around the world, whose inspiration was real guitar players, you could then see how bizarre a human achievement it is. What especially lends weight to this theory is the fact that the Finns have almost made an Olympic sport out of air-guitarring, with full-blown competitions and tournaments. It's as if they've reconstituted the spectacular and familiar imitation of being a rock star, defying RedOctane's efforts to intrude a mundane world with a plastic five-buttoned effigy. Amateurism, I guess, tastes worse freeze-dried into a videogame.
The only other milestone in modern civilization that is similar to this was "pilingual" (fluent in 3.14 languages) Douglas Hofstadter's proposal to write a book filled with reviews about itself:
"I would love to see a book consisting of nothing but a collection of reviews of it that appeared (after its publication, of course) in major newspapers and magazines. It sounds paradoxical, but it could be arranged with a lot of planning and hard work. First, a group of major journals would all have to agree to run reviews of the book by the various contributors to the book. Then all the reviewers would begin writing. But they would have to mail off their various drafts to all the other reviewers very regularly so that all the reviews could evolve together, and thus eventually reach a stable state of a kind known in physics as a "Hartree-Fock self-consistent solution". Then the book could be published, after which its reviews would come out in their respective journals, as per arrangement."
If you haven't already, pick up a copy of his Gödel, Escher, Bach: an Eternal Golden Braid. I could say that I've gotten more from his work, his books, his projects than from the whole of the so-called Cognitive Science field in which I invested two dismal years in for my major, but a rant about the inability of men who study the mind to escape its mechanisms themselves, I fear, is ultimately unfair.