Rethinking iTunes — Looking Back

How it all started

SoundJam MP

As related in this excellent article about iTunes history, before iTunes, there was SoundJam MP, a software that Apple bought from Casady and Greene in 2000. It was essentially a software for listening and managing music collection in MP3 file format. That’s about it. However, it was the first piece of the digital music revolution ignited by Apple when it became iTunes 1.0.

iTunes 1.1
iTunes 1.1

The next milestone for iTunes was the release of version 2.0 which introduced iPod support and MP3 burning. iTunes became more than a simple jukebox software. It became a device management tool too, for better or for worse.

On April 28th of 2003, the iTunes Store was revealed along with iTunes 4.0. That was the first real alternative to CDs and for people to legally get their music. The iPod Photo and iPod Shuffle were released and iTunes had to be augmented in order to support photo syncing. New content type were introduced too: Podcasts. iTunes wasn’t all about music anymore.

iTunes for Windows

On October 1st of 2003, hell froze over and Apple introduced iTunes for Windows. That strategic move by Apple greatly increased the popularity of iPods and the iTunes Music Store. But this was also the start of a tied development of iTunes for Mac with iTunes for Windows. One could argue that this milestone played a large part in Apple’s inability to deliver software that fully took advantage of each platform. In other words, we can ask ourselves: how did the addition of new features to iTunes was slowed by the fact that Apple had to support two distinct platforms? Take photo management for example: on the Mac, Apple was in charge of developing iPhoto. Integration with iTunes was relatively easy: each app could easily exchange data for specific feature support. But on Windows, there was practically no equivalent. Apple chose a very simple implementation: syncing pictures to an iPod Photo was a matter of adding files to a folder then ask iTunes to look into this designated folder to make photo synching a reality. That was it. Another example is contact and calender information: it was available on the Mac before iTunes 5.0 introduced Outlook syncing. That was when the iPods got the capability to display a calender or contacts.

Proliferation of Content Types

Many new versions of iTunes were released in order to support new digital content types: Music Videos, TV Shows, Audiobooks. Movies support came in with iTunes 7.0 on September 12, of 2006. One after the other, they added complexity to iTunes user interface and syncing options. For example, TV Shows were made available with a series of episodes over a period of time. This is quite different compared to music or movies.

Visual Revamps

iTunes 7.0 introduced a major visual revamp, the biggest since its initial release. The next big visual update came with iTunes 11. Most of these were welcomed by the users. This was the third major effort Apple put in order to refresh the look and feel of iTunes. Then, a few visual updates were introduced to match the look of OS X releases.

Entropy Law in Action

iTunes 9.0 introduced Home Sharing, a feature adding not only convenience for the users but complexity too. A look at Apple’s support forums shows that this feature isn’t always working as expected and can be tricky to setup. Still with the 9.0 release, iTunes Extras, and iTunes LP, other kind of digital products, were introduced. Then iTunes 10.0 came out on September of 2010 which brought the malign Ping social network. The second generation of Apple TV was introduced and no longer required iTunes to work. TV Shows rentals were also added to the crowded mix of digital content available.

The Cloud Influence

Two thousands twelve was a pivotal year for Apple and iTunes as iCloud services started to influence its feature set with the release of iTunes 10.3. With iOS 5.0, this was a big step towards becoming a cloud aware operating system. It became possible to wirelessly activate an iPhone and sync with iTunes or update iOS. From now on, people could automatically sync their purchases across many devices as well as download previously bought content. This feature alone was great but it added to the overall complexity of the software. New features often come with more crowded user interface. iTunes 10.5, released on October of 2011, not only introduced the support of iPhone 4S but added iTunes Match and iTunes in the Cloud. These additions helped Apple lessen the need to use iTunes for syncing purposes. Since 2011, our reliance on iTunes to do simple things like install applications, sync content from one device to another has diminished. And this was a good thing.

iTunes in the cloud
iTunes in the cloud feature as seen in iTunes Music view.

A Bloated Patchwork

iTunes 11 came out on November 29 of 2012. Beside its UI redesign that people seemed to like, on the feature side, things were less rosy as we can read in a very bad review of iTunes 11.2 by imore.com on May 12th of 2014:

“I think iTunes is profoundly broken and has just gotten worse over the years. A bloated patchwork, iTunes tries to do too many things and does too many of them poorly. It’s become Apple’s catch-all for media, applications, tethered syncing of iOS devices and iPods and more. And don’t even get me started on iTunes Match. I’ve made my case separately for why I think Apple should follow its approach with iOS and try to divide iTunes’ capabilities into different applications.”

Releases 11.3, 11.4 and 12.0 were introduced to support new devices or new versions of iOS (again). See the pattern here? With new services, new devices, new iOS releases, Apple has to release new versions of iTunes. Same goes with the retirement of some services like iMix, Ping or the Mini Store. Still, iTunes is a complex piece of software for the ordinary people. And it is a complex software to maintain for Apple too.

iTunes icons over the years
iTunes application icon over the years.

In summary, a new version of iTunes is required for one of the following reasons:
– Support a new device
– support a new service or operating system release
– support a new digital content type
– redesign its user interface
– remove a phased out service or feature
– fix bugs, improve performance

With this short iTunes history, we now have the full picture of why iTunes is what it is now. It became a complex application not only because Apple added services, new digital content types or new devices over the years but also because iTunes is a monolithic piece of software that, on the surface, cannot be broken into smaller and more manageable pieces. But, as my next article will demonstrate, if we write down and categorize all iTunes features and the tasks it is designed to accomplish, we can infer six major categories of features that could serve as the basis for proposing a break up of iTunes. Smaller and separate applications could become the best route for Apple to rethink iTunes.

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