Did he ever get beyond a PPL?
Who says that one needs more than a PPL to fly any aircraft on private ops?
Not miserable about much. In Hollywood anything goes and folks strut around in uniforms while making movies all the time, but when an actor also does it in real life, it seems odd.
Some bus drivers have four bars. Some ships captains have four bars. JT with his own fleet, he can wear what he wants to.