So according too you if a man sings or adopts a song written to simply say they lived their life on their own terms, that is somehow meaning they are the same as another person who may have been a thug and who also adopted the song?
I think you need to rethink what you said because it is patently absurd to assign the behavior of one person to another because they like the same piece of music.
The idea is that the singer or the writer is putting forth the idea that they lived life according to their own terms. That is not only an impossibility, but is patently evil.
We have parents, we have neighbors, we have role models, we have the people who provided the food we ate, etc. We live under laws that keep us from doing all the things we actually want to do and would do if there was no controlling authority in our hearts or on our bodies.
Sinatra truly did some evil stuff and paraded his vice as virtue, singing that song and making it his own in every way possible.
Nobody lives their life on their own terms, but Satan tempts us into believing we can.