Cher
Seeing as how Cher is one of the most iconic singers of this and the previous generation, it only makes sense that she keeps a crew of bodyguards around her wherever she goes. This became apparent when, during the early years of her career, someone actually broke through security and physically assaulted the singer.
After that incident, Cher went nowhere in public without at least one bodyguard. For many years, that person was Michael Francis, but as the years went by, their relationship changed from boss-and-client to what Michael called brother-and-sister. He was there with her for three entire decades.