I've wondered why libertarian ideas never seem to get much traction in society at large, but perhaps my time horizon is a little too small. A Reason obit for Ronald Hamowy, the libertarian scholar, written by the important scholar of libertarianism, Brian Doherty, makes the point that libertarianism has, in fact, come a long way:
While he embraced libertarianism for both truth and fellowship, he [Hamowy] told me he was never expecting its ideas to conquer the world--though he was surprised at how far the movement he and his pals helped launch in the 1950s had progressed by the 21st century.
"I thought we were doomed to fail, if we got 50 people in the world who agreed that would be great," he told me. "I still think we’re doomed," he said, laughing. "But now we have more than 50. I really believed [libertarianism] was correct, and I wasn’t going to adopt incorrect views because they were popular, but I didn’t think we were going to go anywhere."
Doherty's article explains Hamowy's role in the movement and links to other articles. Doherty's book on the movement, Radicals for Capitalism, has a chapter that focuses on Robert Anton Wilson.
Here's a great anecdote about Hamowy and Ayn Rand, from Stephen Cox's obit:
One person who resisted Ronald was Ayn Rand. As one of the young libertarians (Ronald’s friend Murray Rothbard was another) who were invited to her apartment for intellectual discussions, he was cast into oblivion after a difference of opinion about . . . Rachmaninoff. Guests were asked to say who their favorite composers were, and when Rand’s turn came, she said “Rachmaninoff,” with specific reference to his second piano concerto. “Why?” Ronald asked. “Because he was the most rational,” Rand responded. At which Ronald laughed, thinking it must be a joke. He knew that the composer had dedicated that concerto to his psychiatrist — and anyway, rationality had nothing to do with its greatness. But Ronald’s laughter resulted in exile, and the loss of friends who were dear to him.