I can't imagine it's being done illegally regularly. It would be way to easy to identify by stream behavior.
I think it depends on local copyright laws, but I think in most places you buy a license to play music publicly and with that license you are allowed to play any music legally acquired.
I think it depends on local copyright laws, but I think in most places you buy a license to play music publicly and with that license you are allowed to play any music legally acquired.