From a fun perspective, sounds a bit odd now but I imagine Robin Williams in his pomp would have been an amazing conversation.
From a professional perspective my old boss's, boss's, boss's, boss's, boss whilst I worked at WPP Martin Sorrell.
From a purely selfish 'fancied her for many years of my adult life' perspective Milla Jovovich (Wife is aware of this infatuation so no fear of announcing this on public forum )