It's chronological and kind of accurate in that it refers to the relationships between the main players in the scene; so unless you know your Loggins & Messina, Michael McDonald (and his affiliates Doobie Brothers, Steely Dan, Christopher Cross), Hall & Oates, Toto et al, you don't really need to see this as the jokes will be largely incomprehensible. There's even an appearance by Hall & Oates manager Gino (aka Tommy Mottola, one-time husband of Mariah Carey), immortalised in the classic 'Gino (The Manager).
I've watched quite a few of them, but picked out the best two;
Firstly the episode where Michael Jackson has a Yacht Rock epiphany by recording, essentially, a Toto song, 'Human Nature' on Thriller
Then the episode where Gino tries to poach both Kenny Loggins and Michael McDonald for management. The bit where McDonald rebuffs him is actually genius
Should you wish to watch all the episodes, then go to HERE
(Apologies if i'm late on this, was introduced to it recently by a friend)