I'm in.
Is the purpose to win or to look like a douchebag hipster who knows whats cool.... "but you've probably never heard of them."
For example, I don't like the beatles but I might pick them just to whore out for votes.
Neither.
But definitely not the second. I actually just did an artists draft on another site and half of the 16 drafters were douchebag hipsters (well, they weren't all douchebags, but 80% of the artists in the draft I'd never heard of).
The point is whatever you want it to be, but I think it works best if the point is to pick your favorites strategically. So if you like the Beatles and would like them on your list of 20 artists, then you might want to pick them first even if they aren't your favorite. If your favorite band is a garage band nobody has ever heard of, then pick them last instead of first.
But really, do whatever you want.