Never really got into any of the shock jocks, they all seemed like coastal phenoms. We had a few on Denver radio for a while who we're alright, but Stern and O&A never really caught on here, not for lack of trying. About the time I got into listening to the radio locally was about the same time the acquisitions and mergers started happening, after Clinton signed the Telecommunications Act that allowed all that. That's when it really started going downhill.
Sirius wasn't around at the time (probably in the planning stages) nor were services like Spotify and Apple Music, and Internet Radio as a whole was still in the maturity stages. Now Apple Music and Sirius (in that order) are my main choices.