The Boston meaning derived from the movie " West Side Story" in 1961. The meaning came from the movie in which the gangs of NYC would use the word " cool ". In Somerville, Ma. in the hub of Boston, Jim Labadini orchestrated the use of this word through out the Somerville school system over 4,000 students. This was intended to be a word that would be unique to kids in Somerville to use to express " how cool" something is in their own terminology. It quickly caught on through out Greater Boston.
Somerville is the most wicked city in Boston.