DAMP: Design Art Mockitecture and Planning

This is Art Lebedev. I assume thats a person, and thats his real name. Lebedev. His work portrays the two most important themes of mockitecture: communication of culture and provocative irony (a.k.a. icons and statements).
The first example of Lebedev's work is the iconic and beautiful mac os 9 speaker icon speaker. An exemplary piece of mockitecture, it is a model for good looking iconography. The reference is there with out being to forceful. It is still legible, however, because it remains a direct image. The question is: Is it possible for an ambiguous, abstract image to retain the meaning inherit in the orginal object(s)? Can direct iconography and formal references be interesting without ambiguity?
Another of Lebedev's designs is the "Fuck the Rain" umbrella. It is a strong message delivered succintly and powerfully to the rain. I'm not sure if the rain would get it, but I do, and I think it is hysterical. From the website:

"From the rain's point-of-view"