Thinking of cool criminality brought one of my favorite singers to mind, the well-known Frank Sinatra. He had many connections to the mob, starting with his career around 1940 the Federal Bureau of Investigation began to keep track of his life and contacts with mobsters. Though Sinatra was popular for his music, surely some people were also attracted to him for his suspected interactions with organized crime. Evidently, some individuals who had mocked or threatened Sinatra received threats from Sinatra's friends in the mafia. At multiple points Sinatra gave large sums of money or lavish gifts to his organized crime associates. His criminal associations definitely aided Sinatra's growth as a star and being seen as truly cool. Sinatra was not cool only for his mob friends, he did have an amazing talent, but who is to say it would have been the same if he had not had friends in higher places. For this tie, Sinatra maintains some type of cool criminality.
Even cool criminality has made its way into the world of Shakespeare. The musical West Side Story is based upon two gangs in New York that portray a modern version of Romeo and Juliet. Though they are not members of mobs, or particularly of organized crime, the gangs do fight and rumble often, which is a crime. Gang violence is evident when Bernardo wishes to fight Riff for one of Riff's former gang friends getting involved with Bernardo's sister. Bernardo is the leader of the Sharks while Riff is the leader of the Jets. Each is cool for his nonchalant attitude to being part of something illegal. Both gangs believe that they have the right to a certain part of the city and they continuously fight over the boundaries of their territories. The production as a whole shows the cool criminality, with its songs and dance routines all tied into the quarrel of two gangs. Cool criminality has many different ways in which it can manifest itself and I believe the more subtle side of cool criminality is found within West Side Story.