Some great questions you've posed here and so many good movies too. I tried watching a few of the movies I watched on repeat as a child and couldn't believe how far acting and screenplay has come since then.
I found your question about Bruce Willis interesting though because I wouldn't necessarily have seen it that way at all. The problem I have with watching movies is that I don't find or make the time to and I don't remember them a month after watching them so it almost seems fruitless 🤣 you obviously don't have that problem.
Usually it's years later when I come up with some of those questions. I saw Armageddon years after it was released, so by then I was able to ask question a like that. Had I seen it in real-time, I wouldn't have asked the question then, either.
Then there are movies like Con Air which had so many supporting actors in it that I thought nothing of them until years later when I discover that before they made the Big Time they had roles in it. John Malkovich, Steve Buscemi, Dave Chappelle, and Danny Trejo are just 4 actors who come to mind.
Con Air, oh boy that takes me back. It was one of my favourite movies in school. Steve Buscemi is brilliant. He has had so many roles and I think is very underappreciated as an actor.
Danny Trejo is a very down to earth guy, he visited South Africa many years back and some people I know got to chat to him.
I think we come up with a lot of these questions once our brain has had time to mull over them. It's weird because I can watch a movie and not think much of it and then watch it again years later and see it from a totally new perspective. Maybe that's the subliminal messaging kicking in 🤣
For some movies, that's definitely it. Not just the classics but the guilty pleasures as well. Repeated viewing, periodic viewing, or even just one viewing after some critical event in life takes place.