One of the most confusing philosophers in American history was Ayn Rand. Not to say her works were complex or hard to understand, she made damn sure the explicit monologues brayed by her shallow characters got the point across. What always confused me about Rand was the fact she had followers.
The only thing I could think of was her psychotic selfish philosophy, built around the idea that there were self made supermen and everyone else was a parasite really resonated with the American fantasy about being self made. One of the greatest, most prolific fictions in the American culture, right up there with White Jesus and Gun Toting Jesus. The American people, even progressives, believe that America was built by self made men, visualizing small frontier forts and homesteads in a barren landscape.
This myth is beyond just the everyday life. Americans live in a modern, civilized society that, with strange exceptions like healthcare, has a very socialized state. Combined efforts built roads and cities, regulate the entire EM spectrum, allowed for the construction of what was once the best telecom and information network, and allowed us to jump into world wide wars virtually unscathed. Somehow, all the people benefitting from this, benefiting from a prestigious school system and easy transport and communications, much of which was pioneered by public effort in this country and Europe, like to consider themselves self made. This causes most Americans to view poverty not as a shitty situation but as a sin, somehow brought on oneself. This causes Americans to ignore the past advances made by public efforts, by government sponsored construction and research, by group effort and claim that they made the predatory millions off of the death of production is all because they were so fantastic.
It really does go back to our foundation. Americans imagine an untamed wilderness, conquered by whites, with silly primitives scattered about and conquered. The reality is very different. The English, one of the last to get on the transatlantic Imperialism, landed to find entire cities and towns, farms and infrastructure abandoned by a heavily thinned out Native American population. Even then, half of the English colonies died off or were killed by the remaining natives. Going south, the English lucked out into older Spanish lands and trading ports, like New Orleans. Americans then managed to annoy the English enough that they pulled anchor to go deal with the French, at the time a major empire.
Due to the lower population, America managed to steal thousands of brilliant minds from countries ravaged by the European wars. Rand like industrialists nearly destroyed America then and there, and only through massive socialization was the country saved. American history is one of luck, cooperation, and external help. The self made image is entirely imaginary, even historically.
But the conservatives in this country don't care much about reality. They are made up of people who hide in ignorance, who desperately want to be the superman, imagining their weaknesses are other people's faults and failing to realize they would be the downtrodden masses in the Randian Utopia. It smacks of racism and xenophobia, of wanting the world to give them everything while complaining about the few dollars from their paychecks that go to the roads they use, or to the people born to poor families. These people are born middle class and above, and they love the idea that they deserve it somehow, as if they earned it in the womb.
Rand is popular because a huge chunk of Americans are pathetic assholes looking for some excuse for their awfulness. The part that really gets me is this simultaneous blame of society for fucking them over, and the adamant declaration that everyone is self made and thusly cannot be society's fault. If YOU fail it must have been socialism or the welfare state or liberals or whatever demons you can find. But when THEY fail it was because they were not the supermen, they were the dirt beneath the supermen's heals.
PS: Good article on Rand more specifically: http://www.opednews.com/populum/linkframe.php?linkid=130609
PPS: On a personal note, I really hate when individualist or existential/nihilist philosophers get dragged into the muck with Rand. Nietzsche is especially maligned, with many calling Rand's Objectivism a progression of Nietzsche's superman. In the sense that Rand had obviously skimmed over some of Nietzsche's works and liked the very poorly understood version of what she thought he had said (keep in mind she was damaged, emotionally and intellectually) and she used many of the same key words, like superman. However, she utterly failed to comprehend even the most basic aspects of Nietzsche's works, even skipping over the bullshit philosophy freshmen love to spout off before they really understand anything they say. She somehow attaches the idea of a philosophic superman with a sociopathic business tycoon. She relates the fact that morals have no absolute definition to 'there should be no morals'. She takes Nietzsche's call to reevaluate morals and ethics without the superstition and self loathing as a call to be a dick, really. Nietzsche had his own philosophical issues (which he actually admitted within his works, making them into open questions) alongside issues like sexism etc, but he also never claimed to offer a perfect system. He in fact said that a new generation of supermen would need to arise in order to seek such a moral/philosophical system. Rand was little more than a traumatized, selfish child seeking unwavering approval at the expense of friends or sanity. She was a cult leader, nothing more.