I think that the key challenge in entertainment in the near future will not be the delivery of enough of a content long tail to make on demand services work for people (critical for the burgeoning on demand TV services), nor the navigation systems that will help unite people with the stuff they already know that they like. But tools that reintroduce serendipity into our entertainment lives, tools that help us discover the stuff we never knew we were interested in.
I pretty much agree that the more personalized and targeted services we get (last.fm, amazon etc.), the more we long for serendipity. Humans probably need a good balance of both.
Earlier today, I had a similar thought: why would I want to hear something similar to Deixa*, if I really love this one song. I don’t because I precisely love this 3 minute song for it’s uniqueness.
* DEIXA (Baden Powell, Vinicius de Moraes)
Album: Vinicius & Odette Lara, Elenco, Brazil 1963