The Leaning Tower of Ping: How iTunes Could Be Apple’s Undoing

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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.

For a full list of my columns, check out the World Wide Wade Archive. You can also subscribe to the column via RSS or e-mail, and you can download Pixel Nation, an e-book version of the first 80 columns, as a free PDF file or a $4.99 Kindle edition.

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Wade Roush is the producer and host of the podcast Soonish and a contributing editor at Xconomy. Follow @soonishpodcast

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