Check out this article on American individualism and it's ties to economic prosperity and vice versa. I'm on board with a lot of what's going on there but I think the causality links are a bit backward. Anderson raises the correlation of counter-culture acceptability and the rise of 'Randian millionares' in periods like the roaring twenties and the sixties but seems to put their success on the loosening of some ephemeral purse-string of American cultural that just seems to loosen at these times.
I would argue that the Randian millionaires came first and in their wake they encouraged a fluidity in the economy that influences social strata leading to dialectics and privilege that become a breeding ground for counter-cultures. Most counter-cultures are directly tied for or against the excesses that the Randian millionaires created: The roaring twenties and the ambivalence of the moneyed populace to the long-term effects of their lifestyles in lieu of it's riches were paid for by these forever young millionaires. In the fifties and sixties the rise of the hippies, beatniks and so on was a kick-back against the American supremism and dollar imperialism of the early Cold War that was funded by rampant consumerism paid for by war profits.
The cause of these counter-culturial and Randian booms themselves also have direct causal links. In the case of both the twenties and sixties - war and the fantastic credit it brought to an isolationist America. In the eighties the third world and its enormous debt became the source of excess for the same libertarian ideals among the young and wealthy while punk, grunge and later hip-hop music all came to embody alternatives - for the middle class who rejected these excesses and working classes who were excluded from them respectively. (I think American governement refuses to recognise class systems so I Anglicise here. (On another note - did you know that Google suggest I spell that Anglicize?))
Anyway, if you take one thing away from the article make it this graph of top tax rates.