After calling myself the Master of iTunes Smart Playlists, I’ve been asked to share some tips.

I can do so, even if I don’t know whether I can tell anyone anything fundamentally new. But then again I also made the experience that many people don’t use Smart Playlists at all or have no idea how they work. Which is a pity, as quite powerful possibilities lurk behind the simplistic dialogue boxes. Must be an Apple thing.

But before we start, there is something to be done …

Get Your Damn Tags Right

Ahem. Well. Making Smart Playlists is much easier if you have your files correctly tagged. Before you call me names: I haven’t it perfected either:

With almost 13000 tracks, managing gets slightly nasty. But never fear, for there is you outside brain concerning all things musical called MusicBrainz.

Apart from being probably one of the most extensive music databases out there – and being far more precise than, take Gracenote (formerly CDDB), which is crammed with spelling errors, it has some nice taggers available for all kinds of operating systems.

The one working for me is the unfortunately slightly outdated iEatBrainz!. Since it’s freeware, you probably shouldn’t complain too much. Using fingerprinting, it will try to guess your tracks’ tags. It’s interface is clearly more intuitive than that of MusicBrainz’ own Picard and it works nicely along iTunes.

Not only will that facilitate creating Smart Playlists, it will also give you better statistics on last.fm, should you happen to have an account there.¹

Even if some information is not in MusicBrainz, you can either get an account there and add that information – or just follow the various Tagging Style Guidelines which seem in my opinion quite sensible, even more so when it comes to classical music, which the design of ID3 Tags has clearly not meant for.

Put Audiobooks Where They Belong

When I listen to music, I don’t want to be talked to. As your iTunes library grows larger, it may contain also audio books – which may no be necessarily from the iTunes Music Store. As MP3, they won’t be bookmarkable, which makes iTunes assume that they are music. Wrong. Teach it right.

To do that easily, head over to Doug Adams’ excellent compilation of AppleScripts for iTunes and download and install Make Bookmarkable.

Choose all spoken MP3s and …

1. Convert them to AAC using the menu command Advanced > Convert Selection to AAC
2. Leave the selection and choose the script Make Bookmarkable from your Scripts. Now, all those files should move from your Music to your Audiobooks library.

In my case, that means listening to Rachmaninov’s Isle of the Dead won’t be followed by example listening exercises from the Certificate in Advanced English. Much nicer.

Now, next time I will show you some basic Smart Playlists that, on their own, won’t do much, but having them around will make setting up other Smart Playlists really comfortable.