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 li...