Ode to a Fallen iPod

September 9th, 2014—a date that still lingers in my personal infamy. That was the dark day that Apple officially discontinued the finest portable music player ever devised, the 160-gigabyte iPod Classic. And just the other night, January 7th, 2025 marked the sad moment that my own trusty iPod, which I’d cherished and nursed along for twelve years, finally gave up the ghost as I labored over a pot of gumbo.

Sure, the grand old iPods were limited and idiosyncratic technology, relying on click wheels rather than touch screens and lacking any way for users to listen to their music without headphones or separate speaker systems. The old headphone jacks were cheaply made and tended to wear out after a few years. But for highly persnickety music fans, the sort of obsessives who collect bootlegs and quibble over alternate takes, mixes, and live performances, there’s never been an easier way of carrying around a large and exactingly curated music library with exquisitely customized playlists.

I’ve mentioned before that I’m a huge Bob Dylan fan—enough to be actively perturbed by the many historical inaccuracies in the otherwise pretty solid A Complete Unknown, now in theaters. When I want to hear “Visions of Johanna,” sometimes I really want to hear “Seems Like a Freeze Out” as recorded with The Hawks from the off-label Thin Wild Mercury Music, as opposed to the more familiar final product. Often when I’ve got a jones for “Tangled Up In Blue,” it’s the 1978 live ‘Grand Ballad’ version that most scratches that itch. Whenever I listen to Bob’s fevered LP Street-Legal, also from 1978, I prefer the original hazy mix (reflecting the chaos and upheaval around its composition and recording) to the excessively bright and digitized remaster that became the new standard as of 1999. And I get a headache trying to listen to the brutally brickwalled mix of Modern Times from 2006, designed to compete on commercial radio in sync with a high-profile Apple ad campaign, as opposed to the more supple version that was only released on vinyl.

It's a tremendous cultural boon that so much of this formerly inaccessible material has become much more broadly available, when at one time you had to know somebody who knew somebody to hear most of it. But those at best semi-legal bootlegs aren’t on any of the standard streaming services, and while it’s great that they can frequently be found on Youtube and Vimeo, they’re still subject to sudden arbitrary removal at any second. Online resources have become too tenuous to be relied upon in this era of censoriousness and capricious copyright claims, regardless of Big Tech’s latest party line, and unreliable for assembling and maintaining a deep music library. With the old iPods, the listener had control; in the streaming era, it’s corporate apparatchiks in the driver’s seat. Yes, iCloud does allow users to import their own files, but what about those times, as on an airplane or the subway, when one wants to listen to music but lacks connectivity?

In statements at the time, Apple CEO Tim Cook claimed that iPod Classics were being discontinued because the company had run out of parts and that demand wasn’t high enough to justify an expensive redesign. Perhaps—I’m not privy to Apple’s internal numbers—but I tend to think that (the failure of Neil Young’s PonoPlayer notwithstanding) there would be at least a boutique market of music enthusiasts who would pay handsomely for a dedicated music player with a user interface closer to an iPhone and capacity more like 500 gigabytes or even a terabyte to accommodate either higher-quality digital files than MP3s or a ludicrous amount of songs.

No, my suspicion is that the primary motivation was to help accelerate a broader shift to a subscription model rather than ownership model for digital content, where instead of paying a lump sum to add an album or movie or computer program to their own collections, users are compelled to continually pay for contingent access to things they have no ownership over. As the World Economic Forum put it, “You’ll own nothing. And you’ll be happy.” The writing was on the wall: by 2014 Apple’s iTunes software was becoming markedly less functional for those of us with sprawling collections of digital music files, unsubtly nudging users to the soon-to-be-launched Apple Music streaming platform. That’s why, even in 2025, I’ve been low-key boycotting Apple and still running a 2012 iteration of iTunes, no matter how many times it prompts me for a software update.

Some might argue that the subscription model is an improvement, that it’s easier for listeners and saves them the time and expense of painstakingly building their own collections. I can understand why that might be preferable for most. But even if the streamers offered all the content I could ask for, their algorithms remain too blunt an instrument to deliver the playlists I really want to hear. And I’d remain at the mercy of cancel culture iconoclasts still eager to erase any media that transgresses against 2021-era pieties. At a time when half a dozen Dr. Seuss books were not only withdrawn from publication but banned for resale on eBay, I was astonished that the Stones’ “Brown Sugar” wasn’t simultaneously deleted from every platform. Regardless of whatever questionable #MeToo allegations, no self-righteous censor should have the power to stop me from listening to Ryan Adams.

Fortunately, I’d planned ahead. By Spring 2014 I’d heard rumors and was dreading that the iPod Classics’ days were numbered, so I’d taken the trouble to stockpile a number of spares before the axe came down. And so, once I find the time to reconstitute my playlists, I’ll be right back to accessing my music on my terms, no matter what the would-be Savonarolas of the world think. Nothing good lasts forever, and the time will inevitably come when my last spare iPod bites the dust, but I hope to be rocking my vintage gear well into the 2030s.

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Next: Ill Legal

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