It's a bit hard to imagine, but there was a time when Rush Limbaugh was "cool." I knew lots of guys in college who became dittoheads and aspired to be like Limbaugh. I guess being a rich bloviating asshole who chomps cigars and golfs was sort of the ideal life path for a certain kind of guy at that time. And I get it in the sense that at that moment... it wasn't quite clear what other life paths were available. It was either be the rich bloviating asshole who chomps cigars and golfs or... be the poor asshole who can't afford such things. The options seemed narrow, at the time. Rush Limbaugh did good.
And of course there was the racism and the anti-feminism and the homophobia and, again, the general license to be an asshole without consequences (or, in fact, to get rich off of being an asshole). The details have changed quite a bit since then, but the general attractiveness of that worldview to a certain set of impressionable 20-year-old males hasn't changed all that much. Swap out golf and swap in video games. Swap out Rush Limbaugh and swap in actual Nazis.