i think what appeals about itunes is the "autorate" database... from what i understand, it will do all kinds of "magical" monitoring of your actions, like skipping a song, look at time of day, type of music, time of year and whatsnot, and then re-sort the whole playlist based on that. and the ipods and iphone share this database with itunes, so that the longer you use both, the more both will learn to "guess" your mood and preferences that day... basically its the same as clippy, only without the attention grabbing avatar. Think of it more like the stereotypical efficient butler or secretary...