Aside from the politics, Limbaugh was "cool." The late 80s/early 90s were weird for a lot of reasons and, I think, weirder than is understood except by the few of us Xers who came of age then. I understand precisely why Limbaugh was cool but find it very difficult to explain well.
It was also when peak life aspiration was getting a home in an upscale golf course development. These things are related.
Our friend Donald Trump also had his fame then. These things are also related.