"The American Dream" has always been a bit of a fantasy, especially as race and class and gender greatly determine who gets to dream, but the basic post-war upward mobility thing in which "we" could all count on some economic stability and maybe even a bit of prosperity if we did what we were supposed to do has fallen apart. I'd say it started cracking during Reagan/Bush...the internet boom papered over those cracks for a bit...then the housing bubble papered over them again... and 10 years later, everything is fucked up and bullshit for The Kids Today.
There are a lot of reasons for this, but I keep coming back to the very simple one: public universities used to be something you could kinda sorta work your way through, and now even public university students are graduating with 30 grand of debt. Too many olds don't understand this. It's depressing.