A eulogy for iTunes: the story of how a piece of software grew to be hated quite so much

What was originally a cute, streamlined piece of software became a bloated victim of its own ambition

FILE - In this Sept. 9, 2009, file photo Apple CEO Steve Jobs talks about iTunes at an Apple event in San Francisco. Apple's latest operating software for Mac computers kills off iTunes, the once-revolutionary program that made online music sales mainstream and effectively blunted the impact of piracy. (AP Photo/Paul Sakuma, File)
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For decades, Apple’s enviable reputation has hinged on the design and usability of its technology. With beautiful devices working in tandem with intuitive software, the company sought to enrich the lives of its customers. One piece of software, however, represented a long-standing blight on that reputation. Contrived, convoluted and confusing, iTunes has found itself on the end of blistering criticism while remaining a necessary evil on millions of computers worldwide.

For many years, anyone who owned an iPhone was obliged to use iTunes to update their phone, to back it up or to move content from it. Whether you used a PC or a Mac, wrestling with iTunes became a compulsory chore, and dislike of the app became widespread.But this week saw it finally put to sleep. With the launch of a new Mac operating system named Catalina, iTunes has been chopped into pieces and redistributed, bringing 18 years of dubious history to an end. But why did it end up being hated quite so much?

"I hate iTunes, I think it is the worst software ever, it's so heavy and just takes over your computer!" howled one online comment. "It is a pox on my existence and it has cost me hours of pain and suffering," moaned another.

A brief history of iTunes

It wasn’t always this way. Back in 2001, the launch of iTunes represented a critical point in digital culture. It gave digital music formats equal status to physical formats such as CDs, and bestowed them with legitimacy in an age of music piracy.

The Associated Press reported on it with enthusiasm, describing it as a "small but feature-laden program that organises MP3 files and lets you rip CDs and burn the music onto CD-R or CD-RW discs".

Less than 3Mb in size, it paved the way for the launch of the iPod some nine months later and the iTunes Store 18 months after that. "We think people want to buy their music on the internet by buying downloads, just like they bought LPs, just like they bought cassettes, just like they bought CDs," said Apple chief executive Steve Jobs.

Scroll to the bottom to see a comprehensive timeline of the history of iTunes.

But they had little choice in the matter. By 2013, Apple was responsible for 75 per cent of the digital music market, all handled by iTunes software.He was right. Jobs's hunch that the music industry needed Apple's help in its fight against file sharing networks such as Napster proved correct, and record labels climbed aboard. By the follow year, Apple had made a million songs available in digital format via iTunes, changing the way we consumed music. Not everyone was happy; many artists and record labels resented the way that Apple's focus on per-track purchases at 99 cents each was changing the way music was made and promoted.

How iTunes became more than just about the music

But music was just the beginning. Jobs envisaged iTunes as a digital hub around which all other devices – phones, tablets, cameras, music players – would revolve. Video and podcasts arrived in 2005, movie rentals and apps for the newly-launched iPhone in 2008, and books in 2010.

What was originally a cute, streamlined piece of software became a bloated victim of its own ambition – but features were being added for music fans, too. Genius, which compiled playlists of songs that “sound great together”, came in 2008, followed in 2011 by iTunes Match, which stored your existing music library in the cloud for a monthly fee.

iTunes would also receive some devastating PR in 2014, when it foisted a new U2 release on millions of users who weren't remotely interested in it.

In 2015, with streaming services such as Spotify changing patterns of music consumption yet again, Apple launched its own, called Apple Music, transforming iTunes into a “toxic hellstew”, as one critic put it.

“iTunes is designed by the Junk Drawer Method,” pronounced blogger Marcus Arment. “[By] adding and heavily promoting great new features that are really important to the company’s other interests and are absolutely non-negotiable, the only thing they can really do is hide all of the old complexity in new places.”

As a result, simple tasks such as finding files, moving them about or even away from iTunes altogether became difficult. iTunes would also receive some devastating PR in 2014, when it foisted a new U2 release on millions of users who weren’t remotely interested in it.

The digital hub envisaged by Steve Jobs had essentially become too unwieldy to cope with the breadth of people’s digital lives, but this fact was never properly acknowledged by Apple until June of this year.

The software became a victim of its own ambition

Craig Federighi, the firm’s senior vice president of software engineering, delivered a sarcastic keynote on the subject of iTunes, which by then had become almost literally the elephant in the room. “Customers love iTunes and everything it can do,” he said. “But if there is one thing we hear over and over, it’s can iTunes do even more? I think it can. Like how about Calendar in iTunes? Could we take it further? I think so. How about Mail in iTunes?”

Federighi’s joke was, in fact, a preamble to the announcement of iTunes demise. It had already receded into the background on iPhones and iPads, replaced with apps for music, video and books, but now the Mac was set to follow suit, with new apps entitled Music, TV, Podcasts and Books. All the digital files that iTunes once looked after would now be divided up into four more sensible categories. The iTunes Store would take custody of the name, continuing – at least for the time being – to sell music and video. And the pesky management of iPhones and iPads which had foisted iTunes on so many of us in the first place? That would be taken care of, as it probably always should have been, by Finder, the Mac’s file management system.

These changes have been designed to bring a sigh of relief to Apple customers. In truth, not everyone is happy; DJs have already found that the new Music app breaks crucial links with their DJ software, while PC users are doomed to battle with iTunes for the foreseeable future. But the death of iTunes marks the passing of an era. Battered, ageing pieces of furniture which neither look nor feel comfortable have to be thrown away eventually. iTunes is that battered chair. It’s time for it to go.