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Interesting write-up. I haven't seen the film in almost 20 years now so it's hard to remember specifics, but I can understand your sentiments.
Maybe I'll re-watch it soon to see if my perspective has changed at all. One thing I remember though is that I felt like there were no likable characters--no one to root for--and that was a problem for me.
I think part of the subtext there, is we live in a society where people aren't encouraged to share their feelings. Any emotions that are inconvenient, you're supposed to just keep to yourself. Every single character in that movie is going through their own existential crisis. If they could open up to each other, they'd probably find they share some of the same problems and could help one another.
But all of their relationships are fundamentally broken, whether family, friendships, or romantic. The only two people that appear to share any sort of intimacy are the daughter and her boyfriend, but they're too emotionally damaged to relate to anyone else but each other. That's why they leave. Lester tries briefly, but he's become too emotionally disconnected from his wife and daughter. Unable to repair his domestic relationships, he concentrates on personal freedom and empowerment.
I think the self centered nature of the characters is on purpose, to illustrate how jaded, narcissistic, and broken people become in a culture that doesn't encourage honesty, self expression, and healthy emotional relationships with people around you. We were in a time of great financial prosperity, yet depression was going up, drug use both legal and illegal was on the rise, all that focus on material wealth was taking our focus away from the things that really matter in life. That's my take away anyway, I think it's a very complex film that has a lot of layers going on.