When one visits the rooms dedicated to Velásquez in the Museum of Prado, it is extraordinary how portraits of kings and those of jesters and peasants are laid side-by-side. The nobility and dignity given to the lower members of the court exemplifies an early example of a revolution in the politics of representation. In the antipodes of this example, we analyse how the campaign of the millionaire Michael Bloomberg to be the Democratic Candidate for the 2020 elections hired companies to produce nonsense memes and digital propaganda. Our hypothesis is that on the center of its strategy the goal was to create an image of Bloomberg that besides viral would be relatable and humorous. The article overviews the evolution of the portrait as an element of political of representation and reflects on how the development of modern and contemporary art transformed the art of political portraiture. Furthermore it deliberates on the two-way appropriation of representation techniques between art movements and political movements.