I'd like to give these vtubers a try but I'm not really sure where to begin watching. Can anyone recommend some sort of introductory playlist? I'd ideally like to find a bunch of half-hour videos that I can watch while working out on an exercise bike and that will give me a solid idea of what the deal here is.

Here's a Best of 2023 compilation for Hololive EN. It's a little over 3 hours, but the individual clips are 30 sec-2 minutes in length, so you can stop and start as needed.

From there, I'd say either look up the channel of somebody you like (or even just describe them in here if you don't catch a name, we can ID them), or if no specific one jumps out but you want to keep trying, then give us a style of gameplay and/or vibe you're looking for and we can throw some suggestions.

"This is probably a stupid question, but . . ."

I'll be honest, I can't even really remember how I got into the fandom. I think it was a gradual thing, as I play Azur Lane which has had collabs with both Kizuna Ai and Hololive in its history yet I took no real interest in the industry until 2020 at the earliest when fanart sites got bombarded with HoloMyth art and memes. Then YT started pushing clips in front of me until I watched and...yeah, it just went from there. So yeah, I'd agree with the advice of just watching a few clips and seeing if anybody catches your eye.

LAST EDITED ON Mar-01-24 AT 00:59 AM (EST)
 
Yep, clips are where to start. I began with seeing clips of Korone back before Hololive had an EN branch. And don't write off stuff too quickly. I originally found the Japanese streams annoying and only did translated clips, but a few months later I was putting on Japanese streams for fun, despite understanding only like 0.5% of them. I might also suggest The Beginners Guide to Vtubers which should give you a good spread and basic rundown of character traits. Though several of the people featured here have since Graduated (retired the character for one or another reason.)

Edit to add: Also, don't feel like you NEED to follow the scene. It's perfectly okay to find one single streamer you like, or fifty, or even none, just try to keep an open mind, because there's a vtuber for just about any flavor of entertainment you're likely to be into. Just because you don't like one retro gamer vtuber for instance, there's at least six others who may not be as prominent, just under the surface. There's a relative dearth of a couple of combinations of talent and game/music choice in some places (Hololive as a whole for instance has only...six? members who do remotely regular FPS streams for example. But there's indies, or other companies with a better selection.)