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Tough question.
I believe a high point was the boom following WWII... jobs, housing developments, drive-in movies, etc. Middle class expansion.The 1950s were great--at least for white people. Segregation was still the norm in the South.
Some say the country hasn't been the same since the JFK assassination. That was a great shock--nobody dreamed that could happen to a President--though it had before.
Vietnam killed the Treasury, and probably lowered the standard of living for Americans for 20 years after. The same may happen with Iraq.
The rapid rise in college tuitions begun in the Reagan era has dampened the American dream. Working class people used to be able to send their kids to elite Ivy league schools--and actually pay the tuitions. Not any more. You have to either be very poor minority, very rich white, or have your house mortgaged to the hilt. Middle class squeeze.
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