With each new product that Apple (Nasdaq: AAPL) announces, including the revamped Apple TV and the new Ping social network, Steve Jobs reveals a little bit more of his plan to dominate the media universe. But I can summarize that plan's fatal flaw in one word: iTunes.

Don't get me wrong. I think Apple's hardware is unbeatable, and my admiration for it has only grown since I got my first iPod back in 2003. My home/office is virtually an outpost of the Apple Store: with the exception of the TV, the videogame console, and the coffee maker, almost every device in my house is an iGadget of some kind. The operating systems that power my Apple devices are pretty good, too. I love OS X and I'm very glad that Xconomy is a mostly Mac shop. On the mobile side, Android is impressive, but iOS is the slickest and most user-friendly mobile operating system out there, in my judgment.

But there's one piece of the Appleverse that I've always detested, and that's the desktop version of iTunes. The ugly duckling of the iFamily, this program is hard to understand, hard to use, inelegant, and ill-behaved -- in short, the very opposite of most other Apple products. I dread booting it up every day, yet I can't sidestep it. What makes iTunes' deficiencies so infuriating is that the program is indispensable: It's the nerve center that stores all of your Apple-related media content, mediates all of your Apple-related purchases, and connects all of your Apple devices.

The rollout of iTunes 10, the latest "upgrade" to this nearly 10-year-old program, was one of the two centerpieces of Steve Jobs' keynote talk on Wednesday, the other being Apple TV, of which I'll say more in a moment. And the big new feature of iTunes 10 is Ping -- a Facebook-like social network designed to help users discover music by seeing what their friends are buying for their iPods.

I've been playing with Ping, and it seems to have most of the features you'd expect of a media-centric social network circa 2010 -- profiles, friending, news feeds, comments. Plus, of course, you can easily preview or buy the songs or albums mentioned in your friends' news feeds. It's easy to see how Apple might expand Ping beyond music to facilitate conversations around media of all sorts, including movies, books, and mobile apps.

That said, Ping has some serious limitations that, to me, are symptomatic of the larger problems with iTunes. For example, there's no integration with Facebook or even with your contact lists, so it's virtually impossible to find real-world friends to connect with. For a social networking tool, this is a bit of a problem. (Kara Swisher at AllThingsD grilled Steve Jobs on this very issue, and his suggestion for finding friends was to "type their names into search or send them emails inviting them to join.")

And there's an even bigger issue: Adding a social networking interface, on top of all of iTunes' other functions, is like grafting another limb to the forehead of an octopus. It's just too much.

Few people may remember this far back, but iTunes predates even the iPod. It started out in early 2001 as nothing more than a program for ripping CDs and playing the resulting MP3s from your computer. (It was based on SoundJam MP, a program that Apple purchased from Salinas, CA-based software publisher Casady & Greene in 1999.) When Apple released the first iPod in late 2001, it marketed the gadget as a way to listen to your music on the go without having to tote CDs around, and it was at that point that iTunes became the main conduit for getting music onto the device.

So far, so good; as a music manager, iTunes did a decent job (though I had complaints about it even then -- specifically, about the way the program organizes music files on your hard drive). But what has happened to the program since then -- starting with the addition of the iTunes Store in 2003 -- is the very definition of cruft. If this isn't a term you're familiar with, let me quote the best explanation I know, which comes from Neal Stephenson's In the Beginning Was the Command Line:

All of the fixing and patching that engineers must do in order to give us the benefits of new technology without forcing us to think about it, or to change our ways, produces a lot of code that, over time, turns into a giant clot of bubble gum, spackle, baling wire and duct tape surrounding every operating system. In the jargon of hackers, it is called "cruft." An operating system that has many, many layers of it is described as "crufty."

If you're not convinced about iTunes' cruftiness, let me take you on a tour of the program's main functions. This is a long list, but bear with me:

  • It lets you rip CDs to digital formats and play the new files.
  • It lets you burn new CDs from your digital files.
  • It lets you print jewel-case inserts for your newly burned CDs.
  • It gives you several ways of visualizing your media collection, including Cover Flow.
  • It lets you curate your music collection with ratings and the like.
  • It lets you create playlists from subsets of your music collection.
  • Its "Genius" feature can automatically create new playlists based on your listening habits.
  • It includes a music equalizer and other sound processing features.
  • It stores copies of your purchased albums, TV shows, and movies.
  • It stores copies of your downloaded podcasts and iTunes U videos.
  • It stores copies of the iBooks editions, PDFs, and audiobooks that you may be consuming on your iPhone or iPad.
  • It stores copies of all of your iPhone and iPad apps.
  • The Genius function can suggest apps you might like based on your past downloads.
  • It stores copies of your iPhone ringtones (but it doesn't let you make your own ringtones anymore).
  • It connects to hundreds of streaming Internet radio stations.
  • It is the leading podcasting client, automatically downloading new audio and video podcasts to which you have subscribed.
  • It is the gateway to the iTunes Store, which is really seven separate stores for music, movies, TV shows, apps, podcasts, audio books, and university lectures.
  • It's the only way to access the new Ping social network.
  • It's the hub for sharing music across your home wireless network.
  • If you have a new iPhone or iPad, you have to use iTunes to activate cellular or data plans.
  • It synchronizes the music, movies, or TV shows that you buy on your computer to your iPod, iPhone, or iPad, and vice versa.
  • It can transcode video in certain PC formats such as QuickTime into formats that are playable on iPods, iPhones, iPads, and Apple TV.
  • It synchronizes your iCal calendar with the calendars on your iPod, iPhone, or iPad; it also synchronizes your address books and any content in your Notes app.
  • It is the conduit for installing the MobileMe control panel, if you want to synchronize data automatically across your PC and your Apple devices.
  • It stores voice memos recorded using the iPhone's built-in voice memo app.
  • It's the repository for music and video files embedded in documents created using Apple's iWork and iLife productivity applications.
  • It interacts with the Remote app, which lets you control your media collection from an iPhone, iPod Touch, or iPad.

Any program that can print jewel case inserts and share my music preferences with my friends is starting to sound a lot like that giant clot of bubble gum.

It's pretty amazing that iTunes runs at all, given everything the mechanics at Apple have crammed under its hood. But I think that Apple's strategy of using iTunes as the catch-all vehicle for every new feature and function that requires the intervention of a PC is starting to backfire. It's an extraordinarily creaky and unstable foundation upon which to build a new media empire.

I am not a software engineer, so I can't phrase my critique as precisely as I'd like, but I think iTunes' cruftiness shows through in at least a few ways. One is the lack of a consistent organizational scheme or design paradigm. The iTunes interface has not been fundamentally overhauled since the days when the program was merely a music manager. So with each new media type that's added to the menagerie, the iTunes screens grow more confusing. Compare, for example, the way the program displays your songs, movies, TV episodes, podcasts, lectures, books, apps, ringtones, and streaming radio stations. In one category, you get a simple list view. In another, you get a list with thumbnails. In a third, you just see thumbnail or icons. It's an information architect's nightmare.

Then there's the problem of how iTunes manages the actual media files behind all these lists. If you've ever tried to manually copy, move, or back up your iTunes media library, you know how difficult it is just to find the stuff on your hard drive, let alone show iTunes where it is once you've moved it. And can anyone explain to me why iTunes puts movies, podcasts, TV shows, and voice memos into subfolders of the "iTunes Music" folder, mixing them up with individual music albums, while mobile apps are in a separate folder on the same level as iTunes Music? And why is it that I can I use iTunes to synchronize my mobile and desktop calendars and address books, but to synchronize my photo albums, I have to fire up a separate program, iPhoto?

The only antidote for software cruft, alas, is to start fresh. As Stephenson writes:

At some point, one must ask the question: Is this really worth it ...? Should we throw another human wave of structural engineers at stabilizing the Leaning Tower of Pisa, or should we just let the damn thing fall over and build a tower that doesn't suck? Like an upgrade to an old building, cruft always seems like a good idea when the first layers of it go on -- just routine maintenance, sound prudent management. This is especially true if (as it were) you never look into the cellar, or behind the drywall. But if you are a hacker who spends all his time looking at it from that point of view, cruft is fundamentally disgusting, and you can't avoid wanting to go after it with a crowbar. Or, better yet, simply walk out of the building -- let the Leaning Tower of Pisa fall over -- and go make a new one THAT DOESN'T LEAN.

As a daily user of iTunes, I feel like one of those hackers. I just want to go after the program with a crowbar. Better yet, I want Apple to build something new. And my bet is that Apple's engineers feel the same urge. But given everything the company has riding on iTunes, the idea of rebuilding the program from scratch (or more likely, breaking it into several programs, in order to bring some logic to the media management madness) must seem incredibly risky and ambitious.

We all know what can happen when such projects go bad -- can anyone say, "Windows Vista"? So, instead, Apple will just keep adding cruft, until, at some point around iTunes 11 or 12 or 13, the program will simply suffer a total musical meltdown, like HAL doing his rendition of "Daisy, Daisy."

Or perhaps there's a way out. I am optimistic about Apple TV, which, as Jobs emphasized in his keynote, is deliberately designed to be un-computer-like. Asking users to navigate an iTunes-like interface using just a tiny remote control would be patently ridiculous -- and because the Apple TV is a streaming device, rather than a storage device, there's less need for all that complexity anyway. So the Apple TV navigation screens are a model of stripped-down simplicity. They're reminiscent of, but even simpler than, the mobile versions of iTunes (meaning the iPhone, iPod, and iPad versions).

As more and more people get used to the TV and touchscreen approaches to media management, Apple may come under increasing pressure to port this kind of simplicity back to the Mac and Windows versions of iTunes. That's my hope, anyway. The sooner Apple demolishes iTunes and builds a new software tower as the hub for its nifty complex of media devices, the happier I'll be.


More from Xconomy.com:

Wade Roush is Xconomy's chief correspondent and editor of Xconomy San Francisco. You can email him at wroush@xconomy.com, call him at 415-796-3024, or follow him on Twitter at twitter.com/wroush.