I always tell myself I’m going to curate a perfect playlist. I’m guessing it would only be perfect for me though. And while I notate music while listening, I never actually get a specific playlist built.
I think that playlists should have highlighted moods or genres, i.e. The Middle by Jimmy Eat World, C.R.E.A.M by Wu-Tang, and Pusherman by Curtis Mayfield should all be on the list, but shouldn’t all play sequentially.
Additionally, I think it’s meaningful to have it divided by those with entertaining music videos, and those without. That way if there’s downtime, time in between sporting events, or it’s slowing down at 2 am, there’s something for the nits folding pre every hand to watch.
Lastly, while I don’t believe it should be 1,000,000 songs on random, I do think it should cover a wide breadth of genres and decades, but be organized as such to include or omit any specifics/keywords. I.e., I should be able to pull in 90s alt/grunge and 90s hip hop/rap specifically, or pop and bubble pop from 1980-2020.