Joe Pyne was close to today's modern conservative talk -- but he was driven from the air after the JFK assassination; and there were exceptions at a few local stations as you noted.
I lived in Cincinnati and in the 1950s and 1960s there were some really good local "talk" radio. Jerry Thomas and Richard King were two. They were entertaining. There was not the freewheeling politics of today however.
Surely you know of the "Fairness Doctrine" and it's impact upon the free expression of ideas. It was a weapon that liberals used against the modern conservative movement.
See Here "You might also think that they would recall the notorious Fairness Doctrine, which was used to 'harass and intimidate' right-wing radio broadcasts, in the words of one unabashed Kennedy-Johnson operative. When that censorious policy was ended in 1987 by former broadcaster Ronald Reagan, there was an explosion of talk formats that gave voice to popular concerns (for a while, Rush Limbaugh even billed himself as equal time)."
In the early days of modern talk radio (late '80s and early '90s) one of the most oft-heard caller comment was "I didn't know others believed as I do!"
We need the MSM even if they won't admit bias but we damn well need the new media also.
Free speech must be defended as it has always been defended against those who would end it, with blood. Their blood, our free speech.
They caught us unaware with the first "Fairness Doctrine" but never again!
Larry King was king of talk radio. I don't remember the span of years. I do remember this, a caller expressed opposition to increased federal taxes. King responded, "Don't you love your country?" I suspect that the man you mentioned generally agreed with King.
That kind of talk went unopposed in all media as liberals argued that one hour a week of William F. Buckley's Firing Line on PBS was all the fairness the conservatives needed.