I do not understand the appeal of Dylan either, but accept that in the pop world he is influential and respected. I have even played in bands which covered some of his songs and still do not get it. The Grateful Dead also does nothing for me. And I have tried. I have many such examples where I have bought pop albums because of their respected status (e.g., Dark Side of the Moon, The Nightfly, etc.) listened to them with an open mind a dozen times . . . and do not want to imagine sitting through them ever again.
My musical preferences appear to be almost hardwired. As early as age ten or so I was uninterested in the music of my peers and sought out other music. i was immediately drawn to early music (Renaissance, Middle ages) and later to Baroque. It took a bit to make it to the Classical period and the Romantics, but early Modern (Stravinsky, et al.) appealed quite soon.
My guess is many others found resonance in their preferred music early on, be it jazz, pop, etc.
Sadly, it appears the majority accept what was popular when they were in high school/college, stop there, and continue listening to the same pop music for the rest of their lives. Thus, the tired warhorses of audiophilia, the never-ending re-issues of classic pop/rock, the radio stations with a play list limited to a given decade.
But, so what? Listen to what you enjoy.
As a side note, it is remarkably easy to remain current when it comes to pop/rock as restaurants, grocery stores, coffee shops, everywhere music is played. I have music disease and thus must listen of I can hear it. Thus, I am familiar with what is popular.