I think starting with some Billy Breathes stuff was smart, but you might try something like "Taste" or "Character Zero". Maybe "Dog Faced Boy". Since Scott was having a hard time with the vocals, it might make sense to try some of the recorded stuff where the vocals are as good as they're typically going to get.
I'm not sure if the mythology is something that you'll be able to get Scott into. Gamehendge and Fluff and some of that other stuff was really cool to happen upon when you're a teenager, but it's super-stupid stuff as an adult.
Listening to Harris reminds me of why I liked Phish a decade ago, and listening to Scott reminds me of why I don't listen to them anymore. I empathize with both of you. Also, it's just kind of a fun look at how friends interact over issues of taste. I really enjoyed this.
