iTunes: What’s great, what’s not, and how Apple might fix it

Among they smorgasbord of new software and features Apple announced at last week’s WWDC keynote, there were a few notable absences. Improvements to Maps, for example. Or a new version of iTunes.

Of course, this being a developer conference, few informed observers expected a new iTunes—that’s something Apple traditionally announces at fall events for music, media, and iOS devices. But given how much criticism iTunes regularly receives, more than a few people were at least hoping this year would be the exception. Instead, we’re left to speculate on the future of what is likely Apple’s most-used desktop app. So let’s speculate.

Fair warning: I come here not to bury iTunes, but to praise it. Well, I’ll bury it a little. But instead of simply bashing the app, I’d like to also praise the good parts, and to talk about how Apple might again make iTunes great. Because, I admit it, I like iTunes—at least the core of it, the music and media player and manager. And I want to love it again.

Still a lot to like

The old saw “familiarity breeds contempt” rings just as true for software as it does for people. The longer we use a particular app, the more familiar we become with it; the more we master it, the more we find things we wish it could do, or could do differently or more easily. After nearly 13 years as Apple’s media-playing and -management tool, most of us know iTunes well, and we’ve each got a list of complaints.

Yet despite (or perhaps partly because of) the frequent criticism it receives, many of us have forgotten that iTunes is a powerful and—still—eminently usable app. Thanks to its familiar interface and layout, regularly updated over the years to match the current trend in Apple UI, it’s easy enough to figure out for a beginner. When it comes to playing music, creating playlists, ripping CDs (some people actually still do that), and basic management of media, few casual users have problems with it.

But iTunes also packs an impressive amount of advanced functionality, including a good number of features aimed squarely at power users. Smart Playlists, extensive support for tags, and lots of sorting and viewing options let you easily browse, search for, and organize your media—as finely as all but the most persnickety media-phile would like (unless you’re a big classical fan, but that’s fodder for another article). Though audiophiles balk at the lack of support for FLAC and other third-party lossless formats, iTunes lets you play and convert to and from many different audio formats, including the lossless ALAC.

You can import and export playlists, and Up Next (like its predecessors, iTunes DJ and Party Shuffle) makes it easy to queue up tracks for on-the-fly queueing. You get a nifty miniature player for those times you don’t need to see the full interface, and unlike many of Apple’s recent apps—and many third-party media players—iTunes is heavily scriptable, meaning there’s a good chance that even if a particular feature isn’t available within the app itself, you can make it do what you want. And though we all have beefs with the details, iTunes makes it easy to share your library with your other devices and with your family. Heck, you can even still print jewel-case inserts (remember those?).

And consider what iTunes has to handle these days. My iTunes-hosted media collection clocks in at over 20,000 music tracks, around 300 movies, over 1000 TV shows, a couple thousand podcasts, thousands of iOS apps, and a smattering of books, audiobooks, iTunes U sessions, and more. Though I have significant complaints about performance when browsing that content (more on that below), iTunes handles it, and playback itself is flawless. That’s not to say no one has problems with huge libraries—I know some do. But the app handles what the vast majority of users throw at it.

There are smaller, faster apps out there that excel at particular tasks, but whenever I try one, I’m frustrated by what it can’t do compared to iTunes. To paraphrase another famous saying, iTunes is the worst media app, except for all the others.

What I’m saying—and I know this will be controversial in some quarters—is that when it comes to managing and playing your media, few apps can hold a candle to iTunes. Many of us, at one point or another, loved it.

But…

And yet we all have our iTunes issues. Perhaps its because hundreds of millions of people use iTunes, but few other apps inspire, and are subjected to, the level of vitriol we see around the Web.

Some of this criticism can be brushed aside as variations of “It doesn’t do things exactly how I want”—complaints such as “Why can’t I just drag and drop tracks onto my iPod?” have been around for over a decade. But many of the complaints leveled at iTunes are valid. For example, over the years, it’s become bigger and slower. Simple actions like switching between music and movie lists can take seconds rather than milliseconds, and it’s not uncommon to have to wait five, ten, or twenty seconds to search a large library for a particular track. These issues seem to scale in proportion to the size of your media collection.

Similarly, if you have lots of iOS apps, iTunes’s app-management and -syncing features are sorely lacking and can be glacially slow; iTunes still can’t automatically update iOS apps to their latest versions; and while music and video syncing generally work well, app syncing through iTunes can be a frustrating procedure.

iTunes has also gotten a bit more confusing with each version. It’s still mostly straightforward for playing music and watching video, but it now handles so many types of media, with so many different views (and options that change depending on the view you’re in), that it’s easy to get lost in the app and its myriad options.

The root of these issues is, it seems, that while iTunes started as a music player and manager—it’s right there in the name, iTunes—over the years it’s evolved, mostly out of necessity, into a do-everything, manage-everything behemoth. It’s now responsible for managing music, podcasts, audiobooks, movies, TV shows, and iOS ringtones and alerts. It hosts stores for purchasing (and sometimes renting) music, video, apps, and, until recently, ebooks. It includes a streaming-radio service, Internet-radio features, and a podcast directory. It’s also responsible for syncing these categories, as well as photos, to your iPhones, iPads, and iPods. (Hey, at least we no longer have to use it to sync content to the Apple TV, too.)

As a “jukebox,” as Apple originally called it, iTunes is solid, and if being a media-management app was all iTunes had to do, its reputation would likely be a heck of a lot better that it is. But iTunes is no longer just a jukebox, and many of its issues can be attributed to the fact that Apple has had to cram so many features and purposes into a single app.

Split ‘em up

The obvious solution, it would seem, is to break iTunes up, peeling many of its non-music features off into smaller apps dedicated to specific purposes and types of media. Indeed, Apple last year took a step in this direction with the release of the separate iBooks for Mac app, which pulled the iBookstore and your ebooks out of iTunes. And specialization is already the way of the world on iOS, as your iPhone and iPad have dedicated apps for music playback (Music), video watching (Videos), podcast organization and listening (Podcasts), buying and downloading apps (App Store), buying music and video (iTunes Store), and handling iTunes U content (iTunes U).

We can imagine a future where Apple takes a similar approach on OS X. We’d have one app—perhaps still called iTunes—that handles just your audio and video organization and playback. Or, even better, all your video is handled by separate Videos app. These apps would be like standalone versions of iTunes’s Library and Playlists sections. There’d also be a dedicated Podcasts app with a podcast directory, where you could subscribe to podcasts and download and listen to episodes.

We’d also have a separate iTunes Store app, just like on iOS, for buying and renting music, movies, TV shows, audiobooks, and other stuff to watch and listen to. (Of course, anything you buy would automatically appear in the appropriate library/playback app—just like on iOS.) And the iOS App Store would also be its own app, replicating most of the features of the Apps section of today’s iTunes Store. In a perfect world, you could even opt to keep this store from downloading iOS apps to your Mac—buying an iOS app would simply auto-download it to your iPhone and/or iPad.

(Apple could instead go the route it took with iMovie and Final Cut, by throwing out the current version of iTunes and starting over with a single, new app, gradually adding back necessary functionality. But it almost goes without saying that many people would then be upset about missing features. Call it the Microsoft Word syndrome—once you add a feature to a widely used app, it’s tough to remove that feature.)

The problems: Wireless and Windows

Splitting iTunes into separate, more-focused apps seems like a great idea, but what works on iOS presents some considerable challenges on the Mac. For starters, Apple still needs centralized way to configure syncing—to determine exactly what gets synced for each type of data and media—on the desktop.

That need is lessening, but it’s still there. A good number of us here in the U.S. benefit from fast Wi-Fi and cellular-data service, so more and more of our data is automatically downloaded and synced wirelessly—there’s less need to physically tether our iOS devices to our computers. But we’re still in the minority. Millions of people, both here in the U.S. and around the world, don’t have this luxury, so physically connecting iPhones, iPads, and iPods to computers is the only way to get large amounts of data onto those devices. And when you need to sync so many different types of data, it makes sense to have that data in one place, and to configure and control all that syncing from one app. Currently, that’s iTunes, and this convenience is a big reason why Apple has tacked features onto iTunes over the years instead of going the iOS route of separate apps.

But that central app doesn’t have to be iTunes. In fact, Apple used to have a separate app for precisely this purpose, or at least the beginnings of one: iSync. From Mac OS X 10.2 through OS X 10.6, the iSync app could handle synchronization of contact, calendar, and bookmark data. It was much more limited than what’s needed these days, but, interestingly, it supported third-party plug-ins, so you could sync with phones and PDAs that weren’t made by Apple. It even offered more options in some areas than iTunes—for example, you could choose how to handle data conflicts, and you could configure iSync to notify you when more than a particular percentage of data would be changed by a sync.

Apple could resurrect iSync, so to speak, by creating a standalone app that handles all your sync settings. Rather than the simple interface of iSync, it would resemble the sync-settings interface within iTunes—or a cleaned-up version of those screens—but the purpose would be the same: a centralized place to manage wireless and wired syncing.

Which leads me to a second big obstacle to disassembling iTunes: Windows. What many Mac users forget is that a huge proportion—quite possibly a majority—of iTunes users aren’t on the Mac. They’re using Windows. And Apple likes to keep the Mac and Windows versions of iTunes largely in sync, so to speak. Which means that any changes to the Mac version also have to be made to the Windows app. (Some people attribute iTunes’s performance and UI issues, fairly or not, to this cross-platform development.)

This also means that if Apple breaks iTunes down into smaller apps on the Mac, the company must do the same for Windows…or maintain two completely separate user experiences. Neither of those options is especially appealing. The former would mean that instead of maintaining a single Windows app, Apple would have to create and support five, or six, or seven—and Windows users would have to download and install them all. The latter would mean that people would have to learn one or the other media-management systems, depending on which platform they use on the desktop; and if, like many people, you use both platforms, you’d need to learn both approaches.

Time for change

For years, people have speculated that iTunes for Windows has been holding back iTunes for Mac, and it wouldn’t surprise me if that’s (partially) true. But whatever the reason, I think iTunes has finally reached the proverbial critical mass: Apple needs to improve it significantly, for both performance and usability reasons. I suspect that a revamp of iTunes is one of the “big things” Apple has promised for later this year.

The question is just how much of a revamp the company has in the works. The proportion of people who can sync wirelessly, and download their media wirelessly (thanks to iTunes Match), is increasing every day. And as more and more syncing happens over the air, there’s less need for desktop software to manage syncing. That would make it easier to break iTunes into smaller, more-focused apps, and it would make Yet Another Windows App less necessary. But we’re not there yet in terms of wireless coverage and costs. Whichever route Apple takes, here’s hoping that, come the fall, we’ll see the debut of a better media-management platform for the desktop—but one that preserves much of what’s still great about iTunes.