I think it's endemic to the entertainment biz. They're gypsies who might occasionally hit the Lotto of stardom, but many toil in obscurity and poverty without ever making it big. Most who do shine sink back into obscurity after a few hits. The difficulty is having to start from scratch after the bright lights and seemingly easy money. I'd say the constant instability and insecurity are prime reasons why showbiz figures will always mostly be welfare statists.
There are many remarkable exceptions. The key element to this “act’s” “position” is that he is a UNION musician— meaning you can’t play ANY large venue anywhere in the US without being in the union (no stagehands will touch a cable or stage items— hence, no show). That’s one. Number two is that this particular bozo started with hid daddy’s oil money to “make it” in the biz— bought his way in. It is easy to do with money up front.
There is a very capable high quality stable of US musicians who have stellar careers without all this “fluff”. Legendary musicians— and they don’t engage in this persiflage and self puffery. This guy is a Dixie Chick— ie. a fraud.