Dylan's a polarizing singer and always was so he'll be minority taste anywhere. Plus most people don't want to be bothered about anything. Try to engage somebody in a conversation; it's surprisingly difficult. After a certain age the mind gets packed away for good. And the young want to hear singers sharing some of their experience if at all possible. Dylan probably couldn't make it now; there's no obvious audience for him.
Because he is polarizing he went decades without radio play in the U.S. Most people here don't seem to venture beyond what the TV recommends; it's an overpowering influence along with the just amazingly massive and unavoidable advertising. I think originally he kind of represented a rebellion against Ad World for me.
The second part you mentioned above immediately made me think of It's Alright Ma. Flesh colored Christs, advertising signs that con etc.
I was recently out of work(back now thank goodness) so in my mind numbing boardom I watched more daytime telly than I otherwise would have and it drove me absolutely nuts!!
Then I had a temporary problem with cable connection and was thankful. Act of God? Not my way.. but thankful anyway. Was in no hurry to get it fixed!
As far as Bob being a rebel against the ad world I think THAT would come over REALLY good today
Well, things have changed. Today, Bob is IN the ads and probably gettin' paid pretty good - Caddies and Victoria's Secret.
And this is why what I call the "Dylan Model" is so awesome. You're doin' great things, playing historic rock with great musicians, living like a king, women on every continent droollin' over you. Sickening. There's no better path, is there?