The 15-Year History of iTunes
Jobs then introduced iTunes, arguably the most important software Apple ever released, other than its operating systems. iTunes set the tune for the company’s next decade and its rise from a “beleaguered” hardware and software company to the industry leader we know today. Admitting that Apple was playing catch-up, Jobs said, “We’re late to this party and we’re about to do a leapfrog.”
And they sure did.
[…]
In my writings about iTunes—notably my Ask the iTunes Guy column—I field questions from users perplexed by the quirks of this app. I used to get questions asking how to do something more efficiently, and I was able to help people organize and manage their music creatively. Now, most of the questions I get are about trying to work around things that are broken, or how to find features that were once easily accessible. More and more users long for a simple music player that sheds much of the cruft that has built up over the years.
When he started the column, I totally underestimated how much material there would be for it.
Update (2016-01-12): Nick Heer:
For my use, iTunes has become steadily worse over the years, as I’m regularly pushed to purchase more from the iTunes Store and place all my music in iCloud. Neither of those things appeals to me. Yet, I’m compelled to continue using iTunes partly because I sync my iPhone in the old-fashioned way, and partly because I’ve never found a compelling replacement for it.
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Just a bit before that last paragraph in the quote...
"The problem now is that those who want to use iTunes for its original purpose, music, find themselves stuck in a morass of features designed to sell, sell, sell product from the iTunes Store."
I think that statement's on the money.
(Not that iTunes does a great job selling either unless I already know what I want. Pandora does a better job selling me iTunes tracks than iTunes, including Apple Radio, eg.)
