iTunes: An Error Occurred

May 31, 2019

Once upon a time, Apple debuted an application for playing music.

Yes, an application. That’s what we called apps back when dinosaurs roamed the Mac. And one of the most-loved applications back in that ancient era was for playing your MP3s. It was called iTunes.

iTunes, circa 2001

iTunes brought together a shiny interface and powerful library management that Just Worked™. What we didn’t know in 2001 was that iTunes was the first piece of a “digital hub” strategy that would change Apple forever. From its humble beginnings as a nice way to play music, iTunes quickly became the core of Apple’s push into consumer electronics: first the iPod, and later the iPhone.

Two years after its debut, iTunes was already at version 4. The addition of the iTunes Music Store turned a trusty utility into an internet marketplace overnight. The Store completely overturned the music industry and overturned Apple itself, kickstarting its shift from a computer company to a device and services company.

As fortuitous as this path would be for Apple’s business, the frenzied shoehorning of network and sync features into a large existing codebase – inherited from the aquisition of SoundJam MP – brought about the end of iTunes’ golden era.

Later that year, iTunes arrived on Windows. Apple quickly gained a foothold on millions of Microsoft PCs; a base they could add to every time they had the need to support something across platforms. As penance for this, the iTunes team was sentenced to maintain and add functionality on Windows every time Apple launched a new product or service.

And add functionality they did. Over the years, iTunes accumulated features for local music, playing and burning CDs, the iTunes Store, iTunes in the Cloud, iTunes Match, Apple Music, TV, movies, Smart playlists, Genius playlists, podcasts, network library sharing, device backup, internet radio, ratings, iTunes Extras, iTunes U, device software update and restore, media sync, ringtone sync, contact and calendar sync, AirPlay, queueing, Ping, Connect, literally rearranging the icons on your iPhone home screen and – most importantly – displaying a bangin’ visualization of the Hootie and the Blowfish track you just purchased for $0.99.

As the central device and platform hub, iTunes became a leaf on the wind of Apple’s strategic moves. The refined focus of the app’s early days gave way to an era of ever increasing complexity and power.

Of course, with great power comes great technical debt. As iTunes became a mammoth katamari of features tangentially related to media, it failed to become a robust front-end for Apple’s increasingly complex network of media services. UI oddities – ranging from weird modal dialogs to an often complete inability to handle network problems – often belied iTunes’ status as a tired legacy product.

Undeterred, Apple marched forward towards streaming music, introducing iTunes Match, iCloud Music Library, and iTunes in the Cloud – which, believe it or not, are three separate things. While Apple’s marketing team may not have struggled to keep up with this growing array of services, iTunes itself certainly did.

While building the UI for many of these new features using web technology might have been a pragmatic move, it exacerbated iTunes’ struggle to provide a polished and seamless user experience. A move from store pages powered by XML to one fuelled by WebKit never stopped the background drumbeat of glitchiness that often ground the app to a halt.

By 2015, it was time for a reset. With great fanfare and a remarkable performance by Eddy Cue, Apple Music was born. With Apple Music, the iTunes team was finally given the time and space to fully overhaul the app, ditching 15 years of legacy chaos once and for all.

Just kidding, it was just stuck on top of what was already there.

Of course, a focused and clean music-only app for Mac is still the endgame. The real question has long been: when?

Retiring iTunes is a hard thing to do, given the wild web of legacy things it enables. Building a ground-up replacement for music on the Mac is a tall order, especially if they wanted to bring across the powerful library management features that made Mac users fall in love with it all those years ago.

Alternatively, Apple must have at least experimented with bringing the much-maligned but generally more modern Music app from iOS to the Mac. Perhaps they could use some kind of almond-flavoured confection to ease the transition.

Regardless, replacing an app the size of iTunes is a big job.

So we waited. The world turned. Users slowly shifted from iTunes to Spotify. A movie came out about a gumshoe Pikachu and it was somehow not horrible. That is to say, it’s taken a very long time – so long that one might assume there has been a false start or two along the way.

But if the rumour and leak mill is to be believed, iTunes’ end is finally nigh. In macOS 10.15 we will finally see a Music.app for Mac. Surprisingly, this new app is said to be based not on the iOS app or a new codebase, but on the venerable iTunes itself.

There will surely be naysayers that claim iTunes should have been tossed entirely. And admittely, if the new Music app ditches iTunes’ interface but can’t cure its deep and baffling love for obtuse modal error dialogs, I too will bemoan its preservation. But arguing for code to be rewritten just because it’s old has never been the right way to build systems that work.

And whatever the composition and fate of this new app, you really have to hand it to iTunes for getting this far. Seriously, this app has been keeping the beat for almost 20 years. It has survived a veritable hurricane of scope creep and strategy taxes. It was a key part of Apple’s growth from charming underdog to singular goliath.

And now, it can finally lay down its burdens and get back to its roots. It can cash out its stock options, and once again be a music app. What better way for a vintage app to spend its retirement?

So let’s pour one out for iTunes. Farewell.

© Allen Pike. See also Twitter and Steamclock.