Edward VIII

Widely regarded these days as a fascist, Edward VIII, better known by his post-abdication title, the Duke of Windsor, chafed under the buttoned-down regime of his father, George V. I had this photo above my writing desk for more than a decade, because you have to admire the panache, surely the model for David Bowie at a certain age. Yes, he hobnobbed with Hitler (who reportedly thought he'd make the ideal Quisling king for a post-invasion Great Britain), but everyone should count his or her lucky stars (retrospectively) that he fell in love with Mrs. Simpson, lost the crown ("Lose the crown!"), and left GB to his stammering but far abler younger brother, George VI.