Something that's been talked about every so often is that there aren't representative (generational) pop icons for the past few generations (probably from millenials onwards).
One theory from Japan, that I still remember and think is most likely, is that the democratization of entertainment since the 80s and especially from the 90s onwards with the invention of the internet has eliminated the very concept of pop culture.
Back in ye olde days a person's choices for entertainment were fairly limited, basically a small regional selection. People in the same locale ended up consuming the same entertainment and thus gravitated towards forming similar tastes and directing their fervor on that small selection of entertainment.
Entire generations identify with icons of their time like Gary Cooper, Gregory Peck, Marilyn Monroe, Ingrid Bergman, Elvis Presley, and so on. Entire generations sang "the song of their people" so to speak.
Today, though? Everyone can access any entertainment they want from anytime anywhere. The entertainment consumed by one person is very likely completely different from that consumed by a person right next to him; entertainment has been democratized. There is no longer a "song of our people" because everyone has a "song of me", there are no longer generational icons because everyone has their own icon.
The intense political push from the Left to make any form of social cohesion and loyalty undesirable also hasn't helped. The dismantling and removal of tradition, religion, and nationalism/patriotism from society means there can't be a "song of the people" from outside of entertainment either.
So no, I don't think you're disconnected with today's culture. Rather, today's culture doesn't value social cohesion and unity as much as it does freedom and power. Everyone has their own icon and song, everyone is their own generation.