MattParker said:
Rush is talented and he spent the first 20 years of his career "going town to town, up and down the dial" honing his shtick as a Top 40 DJ. That experience is irreplaceable and, sadly, now largely unavailable. You can't become a lion in radio at comedy clubs or writing for SNL. So, don't look for another radio lion - ever - liberal or conservative. Rush (and Howard) were the last of the breed.
Rush's radio career is actually kinda spotty before he hit it big.
Yes, there were those formative years as "baby DJ Jeff Christie" on an AM outside Pittsburgh (1360) and one in town (KQV "14K"). He did a little radio in Kansas City, and eventually ended up working off-air in the Kansas City Royals marketing department in a low-level job.
It was audio of short form commentaries he did at night (I believe for KMBZ there) that caught the attention of KFBK in Sacramento, which hired him for middays to replace, believe it or not, Morton Downey Jr. (Downey had been canned for some poorly chosen words, let's just say.)
Edward F. McLaughlin, a former ABC Radio exec, picked him up out of Sacramento, moved him to New York City, put him on satellite space he had courtesy of his exit deal with ABC, and...
So, there's certainly some background there, and some "up and down the dial", and it's very unlikely he would have been the Rush we know today without spinning records in Pittsburgh. But he didn't follow the typical "small market to medium market to medium market to larger market to major market" path.