A coke lord and an openly closeted fag walk into a bar...
Your best entry point for Ron & Fez is something familiar to you.
Could be AFRO shows, a simple bit like "Fuck opie and anthony" or "How many 9 year olds?"
but it's gotta be them discussing something you know.
For me, the best entry point is the live 9/11 episode... many reasons:
1.
The debut of Iris, one of the best characters, comes days after 9/11
2. The show had a soft reboot after 9/11
3. Full archives only go back to August 2001 anyway
4. You hear them at their most real, discussing something we all lived through
Ron himself said being forced to go live on 9/11 made him rethink what radio could be.
The time capsule novelty might get grating because there is a lot of dated football and political small talk... But the evergreen bits are in there. September 2001 will help you get familiar with a less libtard Ron, and a more confident Fez. It sets the table, makes the payoff of Fez "going crazy" at the end more meaningful.
There are weak spots like Foul Mouth Elmo, Joe Poo, and sex stunts -- just a corny product of their time. I love Ron but there are moments at XM where I want to strangle him for being such a know-it-all 'too cool for the room' liberal faggot. But he always wins you back later..
Somewhere around 2010, it feels like Ron is done with it all and is trying to get himself fired every day. Shitting on live reads, shutting Fez down every 5 minutes, dead air, they even completely dropped the music intro for a while, and Ron would open the show doing a random stream of consciousness monologue to no one in particular.
I find myself annoyed with Ron in retrospect, as he routinely gives Fez
terrible hippy advice that just makes Fez worse. At a certain point, I wonder if Fez was even gay. At times it felt like Ron was pressuring Fez to be something he wasn't, and to compare himself to other people just drove him insane.