Very good points. I definitely feel that too re the self-consciousness of not enjoying something others say is good. I’ve watched quite a few ‘artsy’ movies over the years (CK included) where I’ve just really not enjoyed it and felt like I was at odds or maybe missing something that the people who rave about it were able to find.
I often find myself stuck between the questions of 'am I just too dumb/basic/unobservant to get it’ versus 'is this an emperor’s new clothes situation where people all blindly agree that the thing is great because they’ve been told it’s great?’
With classics, I think sometimes there’s a bit of both involved, and that maybe we get a little bit caught up in how historically important it is versus whether it actually impresses by modern standards, or even if we would personally enjoy it without the wider cultural context. I haven’t really figured that part out yet, but my gut feeling is that it’s okay to not be one of the people moved by any particular piece of art, even if it puts you in the minority.
I watched a couple of movies recently that got me thinking about the same thing: Wayne’s World, and The Big Lebowski. I enjoyed both, but in different ways, and to different degrees. I found Wayne’s World less interesting, even though I 'got’ it more, and I liked The Big Lebowski more even though I didn’t really understand most of it. But both of them felt like things that weren’t made for me, and ultimately they mostly made me think of a movie (series) I actually really love that seems to share some of the same DNA, Bill & Ted. I guess I just have to accept that my tastes differ from a lot of what’s popular and agreed to be good.