The End of iTunes (Premium)

When Apple released the first iPod in late 2001, it flopped. The MP3 player was expensive, and it worked only with the Mac via a Firewire connection, which was both rare and weird. All of this limited its appeal. But I loved it.

“The iPod is a trendsetting product that Apple’s competitors are destined to copy again and again,” I wrote of the review unit that Apple sent me that December. “The iPod is easily the most usable and elegant portable digital-audio player on the market.”

Apple eventually solved all of the problems with the iPod by switching to the more commonly-used USB 2 for connectivity, by lowering prices and adding more colorful, fun, and less expensive models over time, and, yes, by adding Windows compatibility. Initially, that compatibility came via a kludged-up version of the Musicmatch Jukebox software. But that was a temporary partnership aimed at buying time; a year later, Apple knifed Musicmatch in the back as it does to all of its partners, and released a version of iTunes for Windows.

Marketed under the banner “Hell froze over,” Apple’s then-CEO Steve Jobs hyperbolically proclaimed that it was “the best Windows app ever written.” As we all know, iTunes for Windows was hardly the best Windows app ever written, at least from its users’ perspective. But for Apple, it was indeed the most important step to gaining consumer acceptance of the iPod. And, crucially, in gaining traction for an online music store that eventually exploded to include podcasts, TV shows, movies, mobile apps, audiobooks, e-books, and, most recently, a music subscription service. The release of iTunes on Windows is what enabled the iPhone, the iPad, and Apple’s services business to succeed.

iTunes wasn’t always a piece of crap. In the early days, when it focused solely on music and iPod integration, I thought of it as “an excellent, easy-to-use application and my favorite pure music player.” By comparison, other jukeboxes, like Microsoft’s Windows Media Player (version 7 and newer) were busy, and tried to do too much; they were all-in-one media players. iTunes, at first, was just about music.

As for iTunes for Windows specifically, I described it at its release as “a stunning replication of its excellent iTunes music jukebox and digital-music-download service” but “ported to Windows without even a token gesture toward making it Windows-friendly.”

“Rather than use the readily available native controls that Windows users know and expect, Apple has aped the Mac OS X-style window controls in its Windows version of iTunes,” I wrote. “So, although iTunes for Windows offers Minimize, Restore/Maximize, and Close toolbar buttons, some of them don’t work like their Windows equivalents but rather as they do on the Mac. For example, if you click Restore/Maximize, the window resizes but will never maximize. Not only did creating this UI require extra work but it’s silly, and it makes iTunes stand out like a sore thumb among your other Windows applications.”

Despite these weird Apple-isms, iTunes for Windows did provide all of the functionality from the Mac on Windows, and that’s what we were looking for.

iTunes on both Mac and Windows included Apple’s music store, and those things combined brought a seemingly endless supply of customers. “Suddenly, iTunes and the iPod were no longer niche products,” I wrote of these developments in 2006. “They were mainstream products. And today, they are the best-selling solution for portable audio on the market.”

That year, Apple released iTunes 7—version 4 was the first to appear on Windows—and it was still my favorite music application at the time despite a number of high profile bugs.  “Its new visual browsing features seem to tax the PC’s processor more than do previous versions,” I grumbled. “It takes up more RAM. It crashes occasionally.”

It had also been expanded to support TV shows and movies—at a stunning 640 x 480!—and even iPod games, necessitating a change in the name of the store from iTunes Music Store to iTunes Store. Content prices, previously set at identical costs across each song and across other content types, started evolving to include variable pricing.

By the following year, the first iPhone and Apple TV had arrived, the iPod lineup had expanded dramatically, and Apple was no longer releasing major new iTunes versions. The 2007 release, called iTunes 7.4, was now a “venerable media management tool,” in my words, “a multiplatform front-end to various media types that syncs with Apple’s ever-expanding range of media devices.” By then, I was using iTunes to manage my own music collection, as well as the TV shows, movies, audiobooks, podcasts, music videos, games, and other content that I synchronized with my own iPods, iPhone, and Apple TV.

iTunes for Windows had been downloaded 600 million times by that release. But it had also become “seriously compromised compared to the less popular but original Mac version,” I noted. It had “troubling performance issues” and was “a performance dog on Windows.” And it was “still the instrument of Apple’s lock-in strategy, in which you are forced to use iTunes and its proprietary store’s music and video formats in order to enjoy the iPod, the world’s bestselling line of portable media players. Worse still is the iPhone, which also requires iTunes of course. In fact, you can’t even make a non-911 phone call with the iPhone until you sync it with iTunes. Yikes.”

So, I was still using iTunes, but mostly because I had to. But the dissatisfaction was there, both for the product itself and for Apple’s broader lock-in strategy. By the time iTunes 8 arrived a year later, I had become even less happy about this relationship.

“I’ve always had sort of a love-hate relationship with iTunes, software that’s evolved so much over time that it’s become weighed down with extraneous buttons, widgets, and other UI silliness,” I wrote in 2008. “Too, the Windows version has always been a performance nightmare, a sad joke compared to the responsive UIs of Microsoft digital media applications like Windows Media Player 11 and Zune. And yet, there’s something indelibly enticing about iTunes, something that transcends all the bad vibes I get from this application, something that makes me turn to it again and again. I use iTunes, daily, and I actually like it. I wish it performed better. But I do like it.”

So kind of a Stockholm Syndrome, it seems.

Despite the version number, iTunes 8 was no major upgrade. That era was over.

“iTunes 8 brings with it all the same issues that have compromised previous releases,” I wrote. “It’s slow. It eats RAM like it’s going out of style. It’s buggy (so buggy, in fact, that the initial release caused widespread Blue Screen of Death crashes on Windows Vista; that problem has since been fixed). And its UI is straining under the weight of years of feature additions, many of them pointless.” All that said, it was “still the most full-featured digital media player on the planet.”

iTunes 9, same issues. “It’s just a molasses-slow, bloated mess.”

“I don’t get why Apple can’t just make a good Windows application,” I wrote of that release. “While iTunes 9 does make some concessions towards modern Windows versions—it now features a standard drop-shadow in Windows Vista and 7 and offers the barest minimum of Jump List support in Windows 7—it also continues to go its own way with non-standard (and ugly) window chrome, scrollbars, and other UI controls. Come on, Apple, stop treating Windows users like jerks and make a real Windows application for crying out loud. We are your biggest customer group by far, after all.”

iTunes 10, more of the same.

“iTunes is simply something that we, as Windows users, have learned to live with,” I wrote, despairingly. “It’s a bloated, poorly-written, poor performing pig of a program. But it’s also an absolute necessity for the hundreds of millions of us who use iPhones, iPods, and iPads every day. That’s because Apple’s digital media solutions, while ubiquitous, are also curiously unsophisticated. There’s no wireless sync, no way to simply manage your Apple device from the cloud. No, if you want to use any i-Device, you need to use iTunes.”

And then it changed. Then it all changed.

In 2011, Apple announced iCloud, and it changed the center of its digital media ecosystem from Mac/Windows and iTunes to the cloud. Now, Apple’s devices—including the iPhone, iPad, and iPod touch—could directly and wirelessly interact with a user’s cloud-based content collections. The iTunes requirement began to be severed. And is now utterly severed. For most people, iTunes is no longer required.

Over time, Apple also evolved the mobile apps it created to replace iTunes, and today we see Apple Music, Podcasts, and TV apps that cover all of the main functionality that we once needed iTunes for. And yet, Apple kept updating iTunes for Mac and Windows, in minor ways, rather than releasing native Music, Podcasts, and TV apps on those platforms. (It even brought Apple Music to Android.)

And now, everything is about to change again.

Bloomberg and others are reporting that Apple will publicly announce that it is phasing out iTunes completely tomorrow at its WWDC 2019 keynote. It will replace iTunes, on the Mac, with Music, Podcasts, and TV apps. Can I get a halleluiah?

Can I also get some answers? After all, this change, while long overdue, arrives with lots of questions about the future as well.

First up is Windows. What about Windows?

What’s most interesting about Apple bringing Music, Podcasts, and TV apps to the Mac is that far more people who need these apps and the services they expose are running Windows than the Mac. So, the biggest question about this week’s iTunes funeral—from my perspective—is whether Apple also announces that those apps are coming to Windows.

And in which form, as Store apps or as desktop applications that can also run on Windows 7 and 8.x.

If I were a betting man, and I’m not, I would put my money on Apple not mentioning Windows at all and then perhaps mentioning Windows in passing in a related press release and the Windows versions of the apps will appear in some vague future. Apple, as I’ve described in the past, only partners with others and is open when forced to be, and what the firm really wants is broad control and lock-in for its customers. A Mac-only release of these apps is in its interests, and Windows versions will only happen if they are absolutely required.

And … are they? When Apple first shipped iTunes for Windows, Microsoft’s desktop system was still very much the dominant personal computing platform. Today, that is no longer true. So, what might the company do instead?

There are two options, web and Android.

My guess is that we won’t see web versions of Music, Podcasts, and TV, because their existence would negate the need for Mac versions; Apple, again, prefers control to openness and “native” apps are its go-to.

But Android is interesting. Apple already makes Apple Music available on Android. Android already has many podcast apps, including one from Google. All it really needs is a TV app. And that’s kind of a no-brainer, in my opinion. I would be surprised if we didn’t see an Android version of that app.

The issue here is what kind of usability hole exists if Apple doesn’t create Music and TV apps, especially, for Windows. The size isn’t up for debate: It’s a big hole. The issue is the quality of that hole. Does Apple care at all about those users who need iTunes-like functionality on Windows?

I doubt it. And I could see the firm simply ignoring Windows, despite the size of that audience. (Or, hole, from Apple’s perspective You’re all holes to them, people.)

Anyway, we’ll see what happens. What we know now is that iTunes is dead. And while I have questions and even concerns, I couldn’t be happier about that. iTunes was the source of too many years of shared suffering. It’s time to put this terribleness behind us and move on for good.