At a verbal level LLMs are great: questions like "tell me about hip hop artists similar to MF doom" or "is there anything new like jefferson starship?" can be the start of great conversations. They will talk your ear off about what is going on with tracks like "Dangerous" off the Yes Union Album.
This is a great way to do it, especially when the LLM can actually get to know you. I've been working on a project that combines a persistent music expert LLM session with social listening, and gives the LLM access to YouTube so that it can find things and play them for you immediately. I've got it tuned pretty well now and I've made it available to the public at https://tunistry.com/
I haven't had much luck with LLMs. I can guess it works with famous artists but lots of other things work with famous artists. I asked it to find more tracks like "Hey Baby" (Deadmaus, Mellifresh) and they completely failed to even come close. I couldn't even get a similar vibe.
That's covered by What.cd's Gazelle "spider web of similar artists"
https://litter.catbox.moe/od8vcq.png