In my admittedly non-representative experience, having more managers around is definitely a now-you-have-two-problems situation.
I got a call from a reasonably high placed sales rep who was upset I hadn't contacted his customer. I had to tell him:
"That ticket is a P3 and I currently have 3 P1s, 5 P2s and I don't know how many other tickets."
He asked I make his ticket a P1 (he had the authority to do so).
Hour later he called back to find out what we had done, the answer was "nothing". Again I had to explain:
"I have 4 P1s, 5 P2s and I don't know how many other tickets."
It's amazing how little people understand / care to understand that other people have work to do too...
In terms of self-preservation and your quality of life, I'm surprised you got that call and proceeded to take no action on his priority for an hour.
Bob was actually a good guy, his questions weren't unwarranted, it's just a really good story to demonstrate how people forget that other people are busy too.
This reads as a lesson in miscommunication more than mismanagement. On his first call, he should have explicitly asked for an ETA. (Even if the assumption was you would immediately start working on his ticket.) On the first call, after his ticket was escalated, he should have been provided with the new context.
The solution, ironically, might be inserting a manager between you and him who can better handle communication.
This was very much a situation where things just had to reach a certain point / inconvenience the wrong people before it was resolved.