waffle

January 9, 2001. iTunes was introduced at Macworld San Francisco and it had very little. Its weak side was that it had very little features, and its strong side was that it had very little of anything, but what it had was completely focused on what it did, and what it did was to play and encode MP3s and music CDs fairly unglamorously on Mac OS.

Later in 2001, Joel Spolsky formulated — or at least wrote down — the idea that good software takes ten years and there’s nothing you can do about it. We’re on year seven, and iTunes is also on version 7, although it’s been on version 7 for a while now – coming up on two years. iTunes stayed on version 4 for exactly two years and two months, so it seems relevant to assume that something’s about to happen.

It’s worthy to step back and reflect over what iTunes does right now. Using it, you can:

• Keep a music library organized, including smart (database-like, rule-driven) playlists and folders.
• Encode CD music tracks into a digital audio file and transcode audio/video files to other codecs.
• Buy (and rent) music, movies, TV shows, audiobooks, iPod games, iPhone OS applications and ringtones.
• Listen to internet radio streams and organize, download and listen to (or watch) podcasts.
• Broadcast audio to external speakers, remotely access other libraries and share your own library in three distinct ways — two for streaming (iTunes-to-iTunes, iTunes-to-Apple TV) and one for remote control via Remote (where it just needs the metadata).
• Sync and keep backed up iPods and iPhones and some K-T Extinction Event-era RIO and Nike players.
• Keep current Nike+-data, share playlists on the iTunes Store (iMix), modify equalizer settings, show an omnipresent “more like this” pane (MiniStore), show a visualizer and get CD track names from Gracenote CDDB.

This, even in broad strokes, is still a summary of what, not of how. It accomplishes this in a lot of ways. Even with all this, it manages to miss if not basic, then at least obvious, functionality:

• You have little to no control over the folder hierarchy of a burnt MP3 CD. This is the only place in iTunes that folder hierarchies ever matters, despite what some of you think you know that the rest of us don’t. Metadata databases are good, not evil. Let’s not constrain ourselves to static playlists in the year 2008. On the other hand, MP3 CDs are both static and going to be used as the primary user interface in car stereos. (iPods and iPhones also suffers from this problem for their own metadata databases, but since their contents are not fixed in polycarbonate plastic and since I happen to enjoy the benefits that the metadata produces, the solution to this problem isn’t as obvious or as easy.)

  And yes, most people have iPods these days, and this isn’t an issue for some of them, but the music players that are not iPods also tend to not have car kits or matching car stereos, and even those who do have iPods don’t all have car kits or matching car stereos, which means that you’re constricted to tape adapters, FM transmitters and AUX, solutions that are of varying quality and means you’ll have to fiddle with the iPod controls instead of the car stereo controls if you want to do anything more advanced than change the volume. These people burn MP3 CDs. (Or they all carry MacBook Airs and get around this, somehow, I’m sure.)

• Without resorting to the first-invented-then-neglected “Party Shuffle” mode, I can’t queue up a track to be played next. Party Shuffle itself doesn’t do, since you have to switch back and forth between it and your primary source to just use Party Shuffle as a queue.

• It is really hard to play just one song without manually stopping playback at the end of it.

The biggest problem with iTunes is perhaps just one of software fatigue. A lot of energy has went into adding stuff to iTunes, even if the feature additions were thoughtful. But I can’t remember the last time anything was taken out of iTunes. I can count on my fingers a few features that would probably look different had they been given recent attention. And on Windows at least, iTunes has a legendary reputation for high memory consumption.

For iTunes 8, I wish simply for three things. First, a rethinking of iTunes where someone sat down and added the features back in from the bottom up, making it all click together the way it just won’t if you pile on brick after brick for seven years. I’m not asking for a Cocoa rewrite, although it wouldn’t surprise me if they did, since Safari was successfully ported to Windows. Second, I ask for the obvious gaps to be filled, primarily the gigantic playback-related WTFs.

Third, I ask for some kind of new data smarts feature. iTunes knows so much about my music and how I listen to my music that it’s creepy. It could easily identify clusters of artists or tracks, it could suggest ratings, it could correlate my music taste during sessions with external variables (like weather, local time or stock quotes) and most certainly, it could produce a sort of shuffle where the tracks I consistently skip are less likely to be played for a while. All that’s missing is a little last-mile data mining logic.

iTunes has been stuck in kind of a “device update” rut. The last music playback feature was Gapless Playback in 7.0 fully two years ago; the last organization feature was the addition of separate metadata for sorting purposes. I have high hopes for iTunes in the future, but I’m not sure it’s going to get there by staying the course. I think it’s ready to be iMovie ‘08′d.