Is is possible? Yes.
Technology-wise, you would do the same thing you'd do for language localisation (see this related SE question for the specificities).
Localization refers to the adaptation of a product, application or document content to meet the language, cultural and other requirements of a specific target market (a locale). Source
Seems like the definition fits the icon situation perfectly. W3C actually mentions "Symbols, icons and colors" in their list of customisable elements. Just as it happens with content, images are loaded with cultural baggage.
The apple developers site has some guidelines in respect to internationalisation too:
Create or modify language-specific versions of nib files, text, icons and graphics (especially those containing culture-specific images), audio, and video for each locale. Source
Now, in regards to the cases, that's a tricky one. I still have to hunt down some good uses, but one thing is sure: This is a job you can't do based on assumptions. Feedback or research is crucial.
I found this interesting discussion in meta:
And some nice related articles: