It won't happen for the intrisc nature of (current-gen, at least) AI of being forced within the limits of their training, which deprives the artist of intent - that is, specifically the ability of questioning in some way what came before him.

The point of art isn't "I made it pretty so it has value now", it's "This is how I see the world, am I the only one who feels this way?".

And yes, this is valid even for absolute jerks who couldn't care less about that the other people were thinking at the time, Like Lou Reed for example. The questions in his music were rhetorical and directed at himself in that case. Unfortunately, as Pablo Picasso said, for this computers (or AIs, in this case) are useless. They can only give you answers.