Why do so many practitioners of "crossover" profess to be so deeply offended by the term? It has no inherently negative connotation as far as I can see: it was coined merely to indicate an artist "crossing over" from one genre into another — generally one for which he/she was not previously known. The word itself certainly implies no harm in that.
Many artists have successfully made forays outside what is considered their home territory. Take Eileen Farrell's recordings of Irving Berlin or Rodgers & Hart: I defy anyone listening blind to identify Farrell as an interloper in the pop world. And Cesare Siepi's "I've Got You Under My Skin" — silly, over-the-top and heavily accented as it is — remains fun, sexy and utterly irresistible. In the opposite direction, Sting has earned kudos for his idiosyncratic but earnest ventures into lute song, and Aretha Franklin's accidental appropriation of "Nessun dorma" was a smash hit.
I can't imagine Farrell would have had much objection to the term "crossover," since she seemed to hold dual citizenship in the pop and classical worlds and could travel back and forth over the border confident of a warm welcome whichever way she went. The trouble seems to arise with artists who want to be taken for natives but come across more as the kind of daytripping tourists whose cameras, Hawaiian shirts and socks-with-sandals are a dead giveaway. One suspects there would be less niggling over terminology if the artists in question were not so worried about tripping over the barbed wire and finding themselves caught in no-man's land, with hostile searchlights trained on them from both sides.
— Louise T. Guinther