Music has a time and a season. I mean, can you listen to Pavement in the winter, Aphex Twin after breakfast, or Sigur Ros during spring break? Still knocking around the subject of my last post (URLs for iTunes), I've been thinking about an Apple Script that would use the comment field and iTunes' song ratings system to get you music appropriate to the time of day or year.
Here's an example of how it could work. Let's say you decide that no song embodies the summer to you more than Pavement's Range Life. Since it contains the quintessential valedictory line, "Don't worry, we're in no hurry/School's out, what did you expect," that would seem like a pretty defensible position. Deciding this, you type 'summer' into the song's comment field. Our script then looks at the date, decides that today is a summer day (say you told it that summer lasts from June 1st through August 31st), and then goes ahead and tells iTunes to change Range Life's rating to five stars or, for a finer grained approaced just increment or decrement as appropriate for each keyword it found.
You could use this system to dynamically maintain all your songs' ratings in accordance with the season or the time of day (put 'night' on all the songs on Drukqs, for example), keeping appropriate songs with high scores and inappropriate ones with low. Then, with enough rated songs, simply sorting your library by rating (or using a smart playlist -- actually, you could probably accomplish much of this simply using "comments contains. . ." rules in smart playlists) would get you songs that fit the moment. I'm not sure about it, but I think that 'shuffle: songs' also takes rating into account somewhat (though it's elusive that one with tastes and prejudices all its own and I can't find any independent confirmation).
The more I get all my music into iTunes, the more I'm for Apple's Ideology of Shuffle. It regularly brings me into musty corners of my collection where I find all kinds of overlooked treasures and forgotten objects of nostalgia. This hack, and other possible ones like it, overthrow shuffle's pure Tyranny of Sensibilitylessness by adding just a touch of human choice into the mix, as a gentle guide rather than a forced curatorial march, while hopfully retaining the pleasurable surprises of a random walk through your music library.