At the start of the millennium, Apple famously set out to upend the music business by dragging it into the digital realm. The iTunes store provided an easy way of finding and buying music, and iTunes provided an elegant way of managing it. By 2008, Apple was the biggest music vendor in the US. But with its recent shift toward streaming media, Apple risks losing its most music-obsessed users: the collectors.

Most of iTunes' latest enhancements exist solely to promote the recommendation-driven Apple Music, app downloads, and iCloud. Users interested only in iTunes' media management features—people with terabytes of MP3s who want a solid app to catalog and organize their libraries—feel abandoned as Apple moves away from local file storage in favor of cloud-based services. These music fans (rechristened "power users" in the most recent lingo) are looking for alternatives to Apple's market-dominating media management software, and yearn for a time when listening to music didn't require being quite so connected.

So Long, and Thanks for All the Rips

For longtime customers, threats of "I'm quitting Apple" are the digital equivalent of the eternal promise to ditch Manhattan, San Francisco, or fill-in-the-blank for someplace more affordable and tolerable. But unlike moving out of town, moving out of iTunes is feasible. TJ Connelly—a DJ for the Boston Red Sox, the New England Patriots, WZBC, and elsewhere—wrote the impassioned step-by-step manual "I Deleted My Entire iTunes Library and You Can Too!"

When iTunes, started, he says, it was essentially a music player. That changed with iTunes 4.0 in 2003. "You got the music store, and that was awesome," he says. But the iTunes Store introduced a new set of concerns and UI decisions. To prevent piracy, Apple made it impossible to move music from an iPod or iPhones or iPad back to a computer. More controversially, the iTunes Store locked all files with DRM from 2003 until 2007, when Steve Jobs personally lobbied for its removal.

Apple's frequent function-shuffling in iTunes has long been an irritation.

But Connelly, who's been an Apple user since the 1980s, understands all that. Where it started to go wrong was with the extras no one asked for, and few used. Genius. Ping. Movies. Podcasts. Ringtones. iTunes University. "They just kept adding more crap into the app," he says. "I don't even know how many things just showed up in the task bar that I had to turn off. Then [with an iPhone] mobile apps also end up in the music player to control your phone." (Apple declined to comment in any way for this story.)

Alex Washburn/WIRED

For music collectors looking for an effective tool to play and manage audio files, Apple's mission creep has long been an irritation, and random burps like cross-branded mandatory downloads by a certain stadium rock band given to bouts of self-importance have been easy to LOL away. But Apple's latest attempts to back up users' libraries to iCloud proved outright dangerous. Some users who checked the wrong boxes found their MP3s overwritten with replacement files encoded with digital rights management or with alternate versions of the same songs (Apple forgot to use iTunes Match, according to Connelly). At least one saw his entire collection copied over with 6 million copies of Lorde tracks. Others found themselves blocked from listening to their MP3s on their iPhones until they docked the phone to their computer and renewed the license agreements—even if they hadn't purchased a single track through the iTunes Store. Many waited for the bugs to work themselves out, blinked at the EULA, sighed, and carried on with the updates.

Others are taking more drastic action.

iAlternatives

Connelly's escape route led him to Swinsian, one of the many music players available for the Mac. Many iTunes alternatives work fine as music players, but few are built for long-term file management. The JRiver Media Center offers a PC-like interface for audio organization that can be awkward for Mac users. In a move that sounds familiar, the latest update to OS X no longer supports MediaMonkey, a popular PC alternative to iTunes. There are some open-source alternatives, but for a Mac user seeking a fully operational iTunes-like app that will manage files with the same ease, Swinsian leads the pack. It aims to replicate iTunes' most elegant functions, strip away the bloat, and add some extra tools.

Because of iTunes' dominance, there is perhaps little market for alternatives, give or take an untapped userbase of committed digital collectors.

"I first started writing [it] in 2010, which was before some of the more recent big changes to the iTunes interface," says James Burton, the UK developer who built Swinsian. "The performance of iTunes at the time (when you had a lot of tracks) and the lack of support for formats like FLAC were probably the biggest motivations. It also contained a lot of features that I didn't use and that weren't to do with music. I think by then it already had sections for managing TV shows, movies, books, and apps."

Swinsian

But, as Burton and others have discovered, many aspects of Apple's software seem trivial until they're missing.

One glaring omission is the ability to sync music directly with an iPhone or other iOS device. Some of the most serious collectors can't pack their libraries onto a puny 128GB iPhone anyway, but for most, this remains the biggest thing keeping them trapped in iTunes. If you like your iPhone to stay synced and up to date, you have to stick with Apple.

Another essential iTunes function missing from many alternatives is an equivalent for the preference to "Keep iTunes Media folder organized," whereby the software directly manages files on the hard drive, moving them to correct new folders when a user edits an MP3's metadata tags. This feature pops up in Swinsian and JRiver Media Center, but Burton only added it to the $20 Swinsian recently.

"My excitement at finding something that works this well has given me a renewed sense of faith in the Swinsian dude that I haven't had in a long time in Apple," says Connelly. Because of iTunes' dominance and the unflashy function of the software, there is perhaps little market for alternatives, especially considering the committed digital super-collectors, while sometimes vocal, make up a small percentage of the user base. It's a niche market, and the apps are niche too; Swinsian is a full-time job for Burton, but he is the company's only employee.

The Big Apple

Apple's priorities are unlikely to change. While it might be more user-friendly to separate iTunes' music management functions from its phone software, sales mechanisms, publisher relationships, and other considerations, Apple's clearly decided to go in a different direction. One reason to keep these functions bundled, Connelly suggests, is because the proprietary iTunes software remains the company's only guaranteed foothold in the Windows world. (Again, Apple declined to comment on this story.)

The fact Apple is so entrenched in our devices makes it well-positioned to expand its music empire even further. Apple is hoping to shine a light on new stars in a way its predecessors were never quite able to muster. With the company's latest forays in the platform wars—including the exclusive debut of Apple Music partner Dr. Dre's long-awaited Compton—the battle takes on a cyberpunk sheen, the old world mirrored in the new.

Apple

To Eric Harvey, a staff writer at Pitchfork (which, like WIRED, is owned by Conde Nast) and an assistant professor of communication at Grand Valley State University who studies music streaming, Apple Music brings to mind the old Hollywood studio system in the way the company is brokering exclusives and other deals with stars. "One of the underreported aspects of the streaming platform gold rush over the past few years is the contracting of music superstars to corporate-branded services," Harvey says. "I find it interesting to speculate about the extent of the contracts these musicians have signed with the services, and what they're allowed to do under their stipulations."

Apple even has a full-time tastemaker in BBC DJ Zane Low. Nothing against Lowe, but for music fans with their own collecting and listening agendas, Apple's star-making streaming machine might be the sound of too many interests clashing. While sales of music downloads continue to plummet, the amount of music available through streaming continues to rise. As music production becomes easier and the need for archiving becomes greater, Apple has transformed its software into something that seems less like a library and more like an ephemeral piece of the pop culture it was designed to collect.

Jesse Jarnow (@bourgwick) is the author of Heads: A Biography of Psychedelic America*, coming in February from Da Capo Press.*

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