It's interesting how entropy maps to arts. Some art has almost no surprises, like romantic novels and pop songs. Other forms of art like experimental music and theater of absurd is built around surprises. Depending on your tastes you would seek out art with just the right amount of surprises that keeps you engaged. The brain struggles to find the meaning in consumed media. If it is too easy to find then the content is trivial and boring, if it is too hard then content is frustratingly inaccessible (and often labeled as pretentious). For example the prog rock music is to my tastes a just right mix of familiar structures and frequent surprises.

It is curious how same art piece becomes more enjoyable after you experience it multiple times. For me the song enjoyment peaks around forth listening. It's like brain enjoys repeating same surprises over and over. I'd guess that can be explained by experience of the reward that comes from brain creating a successful model of input that can perfectly predict next parts.

One case that stands out from this predictability-of-art model is modern sitcom format. Generally the humor is built around concept of surprising with punchline, but many sitcoms are just repeating same joke in predictable way. Instead of actual humor they are just broadcasting "this bit right here is supposed to be funny" every couple of seconds. The laugh track creates conditioning that triggers good emotions in people. Just find a sitcom video with laughing track removed and see how eerie they become.

Anyway this is more about how mind experiences entropy, and has nothing to do with information theory itself. For that I would recommend a great book The Information: A History, a Theory, a Flood. The historical treatment of information storage (writing) and transmitting (communication) is especially good.