Nowadays more than one CEO tries to present a "cool" image instead of a generic executive image, even if in reality s/he is corporate and corrupt scum. They're like Mr. Burns with Jimbo's hat.
Some politicians also try to give a less "generic" image. For example, it seems pretty obvious that Boris Johnson's hobo hair was completely calculated, at least once he realized that his hair was "popular". Or Putin some years ago, when he was constantly doing "macho" stuff while shirtless, so that the whole world would see how "badass" he was.
The game's character however isn't a bad guy, just eccentric, and his "style" seems to be genuine rather than calculated, but in any case I think that his "cool" image isn't that far-fetched nowadays.