Almost seems like a reflection of how our culture has gone after the long 2000s. I get reminded of how a lot of left-wing comics and TV hosts that were reasonably well respected in the long 2000s (Patton Oswalt and Sarah Silverman come to mind) went off the fucking deep end once we entered the mid-2010s.
a huge part of that is how much the left regards themselves as being anti-GOP.
"if Mitt Romney/Rick Santorm is offended by my sex that means its a good thing" -accused child molester, 2012
That means that when Trump became the face of the GOP instead of the Jeb/Mitt type of uptight, "no cursing or mocking anyone ever" style conservative suddenly lots of comedians that got famous from offensive comedy now went full 180 and demanded strict censorship of everything. the dirtbag left were able to thrive in trump's first term for basically being an easy medium to not being pro-trump but also not being what the left became.
the same way you have lots of Shane Gillis style guys on the "right" who are basically a center-right mirror of the center-left's dirtbag types. where outside of being allowed to make jokes that piss off the left they don't really care too much for the GOP's politics.
Patton and Sarah and many others on the left who catered to the types now into trump went full on troll's remorse and is why outside of hollywood they're fucking despised.
No one in comedy treats either of them well, especially Patton Oswalt for that stupid post apologizing for being seen with David Chapelle
Opie was a sadistic fuck, but it was great radio.
people forget that the radio in those days was all about one-upping each other and Opie made sure they were kings of shock jocks. Stern was scared and if it weren't for getting canceled they would have replaced Stern outright. Stern's show died with Jackie, and Artie sucked.
There's some alternate universe where Gore wins, the XFL takes off and O&A don't get canceled in 2002 and Stern degrades so quickly that going to satellite is seen as a bitch move and he's now known as "like an earlier shitty version of O&A"
In that same universe Tough Crowd doesn't get canceled so O&A doesn't become a comics hang and Norton mostly fucks off.