http://www.copernic.com/images/mediakit/screenshots/agent-big/x-ad-find-in-results-eng.gif

As you can see, it has the basic “match all” and “match any” functionality, similar to iTunes. But then it also has an advanced option that says “match the following boolean query”. That option does not clutter the interface, but does allow an advanced user to formulate something more sophisticated.

That’s all I’m asking for. An additional 1-line input box in iTunes, that will allow me to craft something more useful.

However, I completely disagree with you that the masses (grandpas, parents, kids) don’t want to be able to create more advanced playlists, in general. For example, imagine a kid that wants to hear all the upbeat kids songs in his/her collection. That kid would want to create a playlist of the form ((artist=”sesame street” OR artist=”schoolhouse rock” OR artist=”electric company”) AND beatsPerMinute > 150). Or a husband creating a romantic playlist for his wife of the form ((artist=”al green” OR artist=”barry white” OR artist=”marvin gaye”) AND beatsPerMinute < 110)

So whether or not the kid or whoever could easily create such a playlist, there is definitely a need and desire to be able to create more expressive playlists than iTunes gives one the capability to do. So this is why I am completely baffled as to why there isn’t even at attempt in iTunes to provide an advanced option, perhaps by doing something graphical as Marti Hearst suggests. There are for sure more people that just myself that need the more expressive capabilities of a richer Boolean formalism.

I apologize if it sounds like I am only picking on Apple; I have the same problem with other information interaction interfaces that try to be everything to everyone, and therefore choose simplicity over the needs of their users. See, for example, my discussion of Google a month ago (here and here). And for that matter, I have a problem with any information provider that tries too hard to appeal to too many users, and lets simplicity dominate in order to do so. Let’s say, for example, Fox News. Fox paints a very simple picture with the way that it reports the news, and it therefore appeals to a great number of people (from grandpas to kids), and is wildly successful. It garners lots of “pageviews”. However, by reducing the real complexity of the world to such simplistic terms, it ends up under-informing all those same hundreds of millions of people. And an uninformed citizenry devalues our democracy as a whole. Now, I’m not so hyperbolistic to say that Fox News and iTunes playlisting are at the same level of social importance. Of course not. I am only saying that there is a fundamental abstract similarity in the attitudes that inform the design process.

I never said iTunes programmers were monsters, nor even (I believe) implied it. I did say: I fully appreciate not wanting to overwhelm the user. But where iTunes falls short is that there is also no way of switching to “advanced” options, or “Smarter” Playlists. And yes, only providing the user with flat Boolean ANDs or ORs, with no ability to nest, is a “crippling” of the general expressive capability of the Boolean logical formalism. I also used the words “obstructed” and “stunted” earlier in the post. Should I have stuck with those, instead? That is, I would like to ask if what has put you off is my terminology, or the underlying ideas?

It’s also possible for a motivated individual to simply write a program (in AppleScript, Python, or Javascript using OSA) that generates a playlist, so even if there wasn’t the workaround mentioned above, you could still do exactly what you want.

But I suspect such a program would be of limited interest since your problem is surely more complex than the needs of the VAST majority of iTunes users.

I like the “filter/flow” interface from the chapter you linked to. Using Apple as an example again, Automator seems to do this a little, but without the branching & merging (last I checked anyway… been a while since I played around with it).

I’ll have to name the dummy/placeholder list “zzz” or something like that, to get it mostly out of the way.

Still, I think iTunes should make it much easier for me to organize my information than this kludge.