So I watched the video earlier.
It's a very bad video. He makes a few decent points, but does the annoying thing (which he is DEFINITELY not alone on doing, and plenty of people on both sides do it) of pointing out extreme points of view, lumping all of the less extreme points of view in with them implicitly, and then just calling it all dumb.
There's a real nuanced and interesting conversation to have about this and pointing out that Johnny Depp doesn't ACTUALLY have scissors for hands doesn't help with that.
But there is no obvious answer. Do I care that James Franco is playing Castro? Nah. Mostly cause I don't like Franco and I doubt I'll see it anyway. But that, said I think there IS a line where it becomes a problem. Not because it's offensive, but because of who is not being invited to the table as a result.
Can straight people play gay people? Sure! Plenty of gay actors working playing both straight and gay roles.
Can British people play Americans? Sure! Plenty of American actors working.
Can American actors play British people? Not well, but sure! Plenty of British actors working.
Can cis actors play trans actors? Ehhhh. I mean, they can! But there actually AREN'T a ton of roles made available to trans actors. Some, sure, but very very few. So in this case, it's more a case of trans actors losing roles to cis actors for trans roles. It's not about being offensive, as much as it is making room for a marginalized group who doesn't have much in the way of opportunity.
There are other examples, but that illustrates the basic point to me. Though, unlike Bill, I don't care about what random liberal magazines or actors say. It's too easy to point out a dumb opinion and call it dumb, and thereby ignore the actual discussion. I'd rather ignore the dumb stuff and have the more interesting conversation. Which he showed no interest in doing.