I admire Orwell for his ability to recognize and show the problems associated with his side of the political spectrum. In Animal Farm and 1984 he is improving the argument against him, even without disproving it immediately... and this is probably as far as is humanly possible to discuss politics rationally.

I only wish that famous people in all political groups were able to do the same thing. Are there any other famous examples? Perhaps Le Guin's The Dispossessed is something similar for libertarians (except that it is less famous, less dark, happens on a different planet, and has a deus-ex-machina happy end).

EDIT: Oops, "The Dispossessed" is not libertarian, but left anarchist society. They don't have private property, if I remember correctly.