100%.
The context has changed, we live in a different world and have different expectations. If you've spent years studying philosophy you'll understand Kierkegaard, if you've listened to music from the 50s you'll understand why the Beatles were so revolutionary, if you watched sitcoms from the 80s you'll understand why Seinfeld was so off the wall.
We as a culture have absorbed these great works into our expectations. Most people couldn't explain existentialism, pop song structure, or postmodern humor but they understand it now at some gut level.