"The grammar of filmmaking has changed dramatically since then"
Yes, it has. But it's questionable if it's been for the better. A bad film from any era is just bad, but I'd contend that a well made one easily crosses the generations. Mention Casablanca for instance, I can honestly say I've never come across anyone who didn't enjoy it or say it's a bad film.
"Watching something from even the 1960s is super weird and kind of alienating."
One has to wonder what you actually like to watch. You likely didn't like Shakespeare at school because it too is dated.
Pity really, you'll have missed a lot.
_
Edit: I'm curious why you find say '60s films weird and alienating. (There's much to criticize but I've never heard that said before.)
First, don't put words in people's mouths. You'll find that doesn't usually engender reasonable discussion.
Casablanca is a good film, but its pacing, storytelling, acting, and direction are all very dated to a modern viewer.
Acting in good films since the 1970s has tended to be far more naturalistic and less stylized, which makes older work feel fake and cloying. That's not always a dealbreaker, though, as you note. It just puts a gulf between a modern viewer and the work that the work has to do more work (so to speak) to bridge.
There's no point arguing with you as we're miles apart, except to say I find most modern films—and many, many old ones unwatchable (usually for different reasons). I just turn them off.
The reasons are many including those that you've mentioned and others especially the pace and horribly tight editing of most modern films/videos—boys let loose with video editors/switching toys instead of the patience and pace of a Moviola. (Incidentally, I've used both.)
Yes, it has. But it's questionable if it's been for the better. A bad film from any era is just bad, but I'd contend that a well made one easily crosses the generations. Mention Casablanca for instance, I can honestly say I've never come across anyone who didn't enjoy it or say it's a bad film.
"Watching something from even the 1960s is super weird and kind of alienating."
One has to wonder what you actually like to watch. You likely didn't like Shakespeare at school because it too is dated.
Pity really, you'll have missed a lot.
_
Edit: I'm curious why you find say '60s films weird and alienating. (There's much to criticize but I've never heard that said before.)