I came across this on Friday thanks to Huw Raphael, an icon of Jesus Christ Pantocrator with an ipod. Paradosis is quite critical of this alteration of this icon. I was going to comment on it but I ended up needing to prepare a sermon at the last minute (I might post on that in another post).
I don't think I entirely agree with the way he chose to criticise the icon but I have to admit that having Jesus wearing the icon makes for a very passive feel, and thus the artist completely misunderstands the role the book of the Gospel or scroll in an icon. One gets the impression that Jesus simply is to receive our conceptions of Jesus and God or something. The book in an icon is not for the person represented to read but represents the viewers reception of the gospel.
Another way to talk about this is that by having Jesus wear the headphones Jesus is isolated from the viewer of the icon, where an icon's movements is always away from the icon to the viewer. Iconography expresses relationship.
I also have to admit that I agree that simply because our culture rejects certain things or no longer sees things in a particular way doesn't mean that the church should retreat from speaking in a particular way or proclaim things that are contratry to the cultures presupositions. In fact it may in fact be in part the role of the Gospel to chalenge those presupositions.
I think he may have some pointed criticisms of some aspects of the Emergent Church movment, though again as I continue to say, those I know in the movement seem to be avoiding these pitfalls.