Harlot to hood in 400 years
Origins of Insults: Punk (n), a worthless person.
Punk has had a long, sordid career as an insult in the English language. Shakespeare used it as an especially dirty word for prostitute in 1602. It came to mean young male prostitutes, particularly those paired up with seasoned railroad bums, evolving by the 1920s to young, inexperienced boy. Inexperienced soon translated to good-for-nothing and criminal, ready to be adopted in the 1970s by British men in leathers and mohawks screaming about politics into a microphone.
(Source: More at MentalFloss.com)
Three degrees of funny