The terms "gullible" and "conventional" have been natural bedfellows ever since the dawn of time. If something's in style or is "popular", most people just accept it without question. They don't think about it, they adopt it. This goes way beyond a discussion of Bob Dylan, needless to say.

Then you have some people (a small minority in any society) who will only accept the extremely unusual! ;-) It's another form of gullibility than the conventional, but it's driven by a different impulse...the impulse to be a rebel against convention. Either way, the impulse gets taken too far.

Dylan may indeed have been playing games with critics and sycophants and seeing just how far he could go. He certainly did that in his interviews with the press at the time (in '65 and '66). Many of the answers he gave them were bizarre, often hilarious, arbitrary, misleading, certainly not to be taken literally, but rather to convey how he felt about the very process of being asked the usual repetitive questions by the press. He was ruthlessly making fun of the process and doing it at the expense of those interviewing him...depending on who they were, and whether he liked them or not.

This ended up, curiously, with interviews that could sometimes be far more entertaining than the standard interview is...provided you could see the humour in it. I think he may have done us all a favour. He certainly made the scene more interesting.