Yah... now that you mention it the author did put ALOT of media/art personalities in charge of countries in that timeline. I mean, Prime Minister Charles Chaplin was believable to a certain extent considering the man's deep interest in politics during the 30's and 40's historically. Lovely inspirational speech he gave, and it served well to detail the differences between the author's "Fascist" ideology and OTL's Intergralism in the sense that it's supposed to crush our sense of empathy and individuality underneath a strict state-mandated war machine; discarding Integralism's notion of Christ's common humanity for one of cultural exclusivity. President Sinclair Lewis always struck me as a rather odd choice for a politician though: a real far cry from President Lindbergh in terms of domestic policy. The possability of America swinging that far to the left, even with an economic crash as massive as the timeline supposed, never really seemed real to me.
EDIT: Linking to a version some fan of the timeline actually made of PM Chaplin's speech from The New Nero online. Full video too: somebody must have really liked it to put this much work in! The author should be proud.
Speaking of media/art personalities, I seem to recall that, in one of the last chapters, the author mentioned alternate versions of H.P. Lovecraft and George R.R. Martin. Am I wrong?