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How iTunes built, and then broke, my meticulous music-listening system

Source: Apple

The design has fallen out of fashion now, but a spreadsheet wasn't the worst model for Apple to use in building iTunes. The more you obsess over your music, the more you appreciate iTunes' rows and columns of data.

Using the app's "smart playlists," you can slice and dice your library to surface parts of your collection you forgot were even there. iTunes delivered me countless half-remembered gems over the years, and for that it has my gratitude. But lately it has fallen apart.

There is an entire field of Apple criticism reserved for iTunes, a cross-platform monolith that serves a bewildering variety of functions.

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It outgrew its origins as a place to manage your MP3s to become the place where you activate new iPhones and iPads, buy TV shows and movies, and access Apple's subscription music service.

It's an app that does way too much, and yet each function is so important to Apple that the company seemingly cannot imagine it doing less. And so each year it does more.

As a music obsessive, I rely on iTunes to do one essential thing: move MP3s on and off my phone. I have long since switched to Spotify for most of my daily listening, but my iTunes collection includes hundreds of tracks that will never become commercially available. Live recordings traded on the gray market; unauthorized remixes; and popular songs kept off streaming services for whatever reason. Take away iTunes and I have no way of listening to Beyoncé's Lemonade, for example. And what sort of way is that to live?

Every day I need to put a selection of these tracks on my phone, without devoting all available storage to music. And so a decade or so ago I decided to build the perfect mobile music listening system using iTunes smart playlists.

I rated nearly every track in my collection from one to five stars and made a nerdy, arbitrary decision: I would listen to each three-star track every five months, and every four- or five-star track every two months. I let iTunes keep track of when I had last heard a song; when too long had passed, the song popped up on a smart playlist. Each day I synced my phone when I woke up, and I would head to work with a fresh mix of favorite old songs in my pocket.

On one hand, the system was never going to work forever. I'm always finding new songs I love, and so every month the task of keeping up with them all grows larger. The size of my daily smart playlist grew from around an hour when I started to more than two and a half hours today. Keeping up with it often feels like a terrible chore imposed upon me by the dorkiest part of myself.

And yet I cling to the system, because every day it brings me a happy surprise. Like my MP3 of Radiohead surprising the crowd at Oxford with "Creep" in 2001, which still reliably gives me the chills. Or the superior original version of the Shins' "So Now What," which was released on a movie soundtrack that is no longer available to stream. Or anything by Aaliyah, who may never come to streaming services at all.

For my system to work, iTunes has to sync. But with each passing year, the act of syncing seems to take longer than the year before. Hours pass by as my phone is "backing up," even if I fully backed up the phone minutes before. And increasingly, sync doesn't work at all. Sometimes I plug in my phone and iTunes doesn't recognize it as a device. Sometimes the dreaded "unknown error" occurs. Most frequently, I get this: "iTunes cannot sync photos to the iPhone … because your Photos Library is not yet available. Please try again later." (I am just learning that there is apparently a fix for this one.)

By themselves, each of these problems is undoubtedly fixable. Taken together, they convey the strong impression that sync is not a high priority at Apple. Even when syncing works, it often takes an unbelievable amount of time. And little wonder: there's no profit in the perfect sync. Apple would undoubtedly prefer that I back up my entire library to the cloud and subscribe to Apple Music for $10 a month and watch all of my problems evaporate.

But even then, I can't figure out how to get all those rare and live tracks to come with me. I can't figure out how to get them stored locally on my phone. I can't figure out how to get them on a playlist that renews itself automatically every day.

My system is unsustainable and arguably insane. I am the edgiest of edge cases. But I'm that way because iTunes allowed me to be. And for the better part of a decade, that let me stay connected to incredible music that likely otherwise would have disappeared from my life. The great thing about desktop computing is not just that it allows nerds to be nerds but that it encourages them to do so. The decline of sync is a small thing, but a revealing one. On the desktop you control your own destiny. On mobile you subscribe to it, for $10 a month.

Commentary by Casey Newton, Silicon Valley editor at The Verge. Follow him on Twitter @CaseyNewton.

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