> Early idealists saw TV as bringing Shakespeare to the masses. We know how that went.
Yes. The masses got to see Shakespeare.
At school we spent a year on Julius Caesar. Now, the problem with these plays as literary material is that they're intended to be performed. The school was able (with support from parents) to ship students to see one performance of the play they were studying at a professional theatre (in our case a Royal Shakespeare Company performance) but for an entire year's English classes that's a pretty poor ratio.
However we could watch (video recordings of) several different TV adaptations of this work during class, we could see a staging with "authentic" Roman backgrounds and a cast dressed in togas, and we could see the same scenes re-imagined as a Present Day drama. Short of having us actually put together a performance ourselves (this was English class, not drama) I don't see a better way to actually teach these plays.
What I'm reading here is the usual nostalgia for an imagined past. If you wanted the Internet to make the masses suddenly better educated and more interested in expressing themselves then you've made a mistake just as if you expected the city park to make the masses healthier and more interested in running. This is infrastructure, it's necessary but not sufficient.
Also, surely the least healthy thing the Internet did so far was create the Twitter pile-on? Which is totally user ability to participate, create and learn, it's just that they will participate in hating today's Milkshake Duck, they will create memes and awful jokes about Milkshake Duck, and they will go out of their way to learn other reasons to believe that actually Milkshake Duck was always awful and anybody who thought otherwise ought to be next in the pillory.