Can I Save My 20-Year-Old iPod?

Some things are worth holding on to

I want to thank everybody who has purchased my book Uncharted Territory: What Numbers Tell Us about the Biggest Hit Songs and Ourselves thus far. So many people came out to support the book that it is sold out everywhere but Amazon. If your copy still hasn’t arrived, I promise it is coming. If you’re an early bird, I will also be on CNN’s This Morning with Audie Cornish tomorrow morning at 6:20AM EST to chat about the book.

If you want your book signed, I am going to be at Little City Book in Hoboken, New Jersey, on Thursday, December 4 talking about the book with the incredible journalist Michael Tedder. Reserve your spot if you’re interested. Now, let’s talk about iPods.

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July 10, 2025

No matter how organized you are, I think it’s always important to have a junk drawer. My family always had one in the kitchen. It was the place you went to when you needed a pen, pencil, rubber band, old mint, or random charger.

But I never thought “junk” was the proper way to describe a drawer like this. Junk drawers are places of dreams and serendipity. They’re where you keep that random USB-to-HDMI cable that you needed for one very specific task ten years ago and are convinced you might need it again. Then while you go digging for that cable you come across an old wallet-sized picture of your sister from kindergarten. Dreams and serendipity.

The current junk drawer in my apartment, albeit mostly filled with musical ephemera

In my apartment, my junk drawer is in my bedroom. Its contents are pretty similar to the one my parents had, except mine is also filled with musical gear. Guitar picks. Tuners. Slides. Dusty harmonicas. While I was digging through the drawer the other day looking for a capo, I came across something truly incredible: an iPod.

This was not just any iPod. It was my first iPod. If my memory served me correctly, I got it back in 2004 when I was in fourth grade. The serendipity of coming across something like this should have derailed my entire day. But I had to practice for an upcoming gig, so I tucked the device back into the junk drawer. I’d try to boot it up tomorrow.

July 11, 2025

Lucky for me, the recesses of my junk drawer not only contained my iPod but also the charger. So, I plugged it in, made myself a cup of tea, and waited. When I returned, things were not going well. The iPod was making a weird noise that sounded like it was about to start blowing smoke out of the headphone jack. Then a frowny face appeared above a URL: www.apple.com/support/ipod.

When I punched that URL into my web browser, lo and behold, it took me to … a user guide for the iPod Touch. Apple had sadly not kept the old iPod support page live. Looks like I was going to be making a trip to the Apple Store.

July 12, 2025

Given that I don’t own a car, the most convenient Apple Store for me to get to is at the World Trade Center in New York City. So, I made an appointment and headed for the PATH train. Should you have the pleasure of not being familiar, the PATH train is a subway that runs between New Jersey and New York City. And it’s a quick ride when things are working.

Painfully for all of us living just across the water in New Jersey, the PATH train is frequently broken or delayed. This is particularly astounding given that it is one of the most important transit arteries in the US. Today, the entire system was down! So, I had to take the ferry into the city. Not the worst thing. It was a beautiful day. Still, the trains should work.

The Oculus at the World Trade Center

The Apple Store I was heading to was in the Oculus, the train station and mall located at the World Trade Center complex. It was built as part of the rehabilitation efforts for the area after the 9/11 attacks, and though it took an absurd amount of time and money to complete, it is stunning.

The Apple Store that I was headed to was not as stunning. When I pulled my ancient iPod from my tote bag, the Apple Genius that was speaking with me reacted as if I had pulled out an abacus. He’d need to take my device into “the back” to see what they could do.

He didn’t leave me waiting for long. It’s not that there wasn’t anything Apple could do; it’s that there wasn’t anything that they would do. My iPod was so old that Apple considered it “obsolete.” Issues with obsolete devices were your problem. Tim Cook and company wouldn’t help you. I headed back to the ferry upset with my tech overlords.

July 15, 2025

I get a text from my friend

Walter Hickey

that I should come out to Brooklyn to see a live show he is helping out with. I’ve known Walt for a few years. And he’s involved with a ton of cool projects. He has a fantastic book called You Are What You Watch: How Movies and TV Affect Everything. He writes the daily newsletter Numlock News. And he’s the executive editor of Sherwood News, a great publication owned by Robinhood. So, when he mentioned this event to me, I was interested.

The event was for Garbage Day, a newsletter that chronicles the best and worst of the web. Walt was helping out. I settled in at the back of Baby’s All Right—the Brooklyn bar and music venue where the event was at—just before it started. The air conditioner was broken, a problem for mid-July, so there was a faint smell of sweat in the air. Luckily, the show was engaging enough to move any odor concerns to the back of your mind.

Ryan Broderick, the man behind Garbage Day

Afterward, I met Walt and some of the Garbage Day folks for a few drinks at a bar in the area. That’s when I started talking to Morry Kolman, another person involved with the show. Somehow we got on the topic of iPods, and Morry told me that he has a friend that was a wiz at fixing iPods. He said that I should reach out to him on Instagram. I was thrilled as I took another sip of my Pabst Blue Ribbon.

July 17, 2025

I reach out to Morry’s friend on Instagram. After sending him a video, he was quick to diagnose the problem. It’s a 4th generation iPod. Based on the sound it is making, I’ve either got a broken or corrupted hard drive. It shouldn’t be hard to fix, he tells me, but before I buy a new hard drive, I should first try to put the iPod in the freezer for ten minutes.

I’m confused. This sounds like he’s giving instructions for how to destroy the parts of my device that still work. He clarifies that if I just have a misaligned hard drive head, the freezer will snap it back into place. Skeptical, I throw the iPod in the freezer. I wait ten minutes, then plug it back into the charger.

A cold, 4th generation iPod

I’m shocked. The iPod is no longer making the weird, chugging noise. Did the freezer just fix a 20-year-old piece of musical technology? The Apple logo appears on the screen. Looks like I’m in the clear. Nope. The same error message appears. Alas, I’m in the market for a new hard drive.

July 28, 2025

As I peruse the internet for how to repair an old iPod, I quickly come to learn that repairing Apple devices is a controversial topic. For decades, Apple has made their devices difficult to repair. Here’s how a popular repair company named iFixIt describes the problem:

Beyond restricting access to parts, companies block repair in all kinds of other sneaky ways. Sometimes they glue in batteries with industrial-strength adhesives. Sometimes they use proprietary screwheads. Sometimes they use software to pair parts to your device’s serial number or motherboard, either throwing up errors for replacement parts or blocking new parts entirely.

This issue goes beyond Apple, though. Technology companies want to make it hard to repair your devices, so you have to buy new ones if something isn’t working. Of course, this is bad for customers. “Would you buy a car if you couldn’t replace the tires?” iFixIt poses on their website. “So why buy a phone if you can’t replace the battery?”

These are valid questions. And an entire “right to repair” movement has sprung up over the last few decades demanding that companies make it easy for customers to repair and modify items that they purchase.

I don’t think the ghost of Steve Jobs is going to haunt me if I repair my ancient iPod. But it seems these questions have only gotten trickier as hardware has become embedded with software that technology firms can continuously update from afar. The Economist described this issue deftly in 2017:

Since the advent of smartphones, consumers have been forced to accept that they do not control the software in their devices; they are only licensed to use it. But as a digital leash is wrapped ever more tightly around more devices, such as cars, thermostats and even sex toys, who owns and who controls which objects is becoming a problem. Buyers should be aware that some of their most basic property rights are under threat.

July 30, 2025

I’m perusing hard drives online. Frankly, it doesn’t seem that replacing it will be that expensive or that difficult. There are tons of YouTube videos on how to do this. But I’m still nervous. I am not handy. I have never been. I likely never will be. And I’m generally okay with that. I have other skills. Because of that, I keep hesitating before making a hard drive purchase.

As I waver, I start leafing through a copy of Steven Levy’s 2006 book The Perfect Thing: How the iPod Shuffles Commerce, Culture, and Coolness. Though it lacks the hindsight of the last two decades and borders on hagiography, it does capture both how innovative and popular the iPod was.

The iPod was not the first device that let you take your digital music collection on the go. But nearly every predecessor was riddled with tradeoffs. Some held a ton of music but were very heavy. Others were light but barely held 30 songs. A few more found a middle ground but had terrible battery life and an impenetrable user interface.

The original iPod, by contrast, was a miracle. It was about the size of deck of cards, held a thousand songs, and made your music collection accessible in a few clicks. Plus, syncing music from your computer only took a few minutes. There was nothing like it. And its sales numbers reflected that.

In Levy’s book, he notes how 730,000 iPods were sold during the 2003 holiday season. Two years later, Apple moved 42 million units during the Christmas season, 28 million more than their original projection. In many ways, the iPod was the product that changed Apple’s fortunes.

August 5, 2025

Though my iPod journey is temporarily on hold as I head to meet my family in the Caribbean for a vacation, it is still on my mind. Before I board the plane, I download some music to listen to offline on my iPhone. This process is always a reminder that we don’t own music in the streaming age. If your streaming service of choice has a licensing snafu, your favorite song will no longer be available to you. This stands in contrast to the iPod model. You could take music on the go but (a) it required no internet connection and (b) you owned the songs.

Now, I’m under no impression that switching from digital purchases to streaming was some industry cataclysm. In fact, it was the opposite. The only company that was making money during the iPod’s heyday was Apple. Music industry revenues were collapsing. It was an open secret that people were mostly filling their iPods with music downloaded illegally from file-sharing services, like LimeWire and Kazaa.

Industry revenues according to the RIAA as seen in my book [Credit: Cailiegh Nerney]

Despite the fact that I work for a streaming service, I’m not going to argue that the model is without flaws. But it’s always struck me that the biggest problem with streaming is how it removes the communal aspects of music. Though I guess lonesome listening goes back to the iPod or even the Walkman. Maybe my nostalgia isn’t all it’s cracked up to be.

August 11, 2025

I’m still in the Caribbean, and I’ve been playing tons of music for my family over a speaker while we relax. Though I am streaming this music, it has reignited my iPod nostalgia. Many of the songs I’m playing are things I learned about while plundering my dad’s CD collection decades ago.

My dad had hundreds of CDs. When I got my iPod, I would dig through the piles for weeks, listening to scores of songs and deciding which to add to my library. This was a nice way for my dad and I to share music. And I’m sure many other people experienced a similar thing during the iPod’s heyday. But how would I share music with my child?

Would I let them scroll through songs that I’ve saved down on my streaming service of choice? Would I make them playlists? Would it all be passed on orally? There is something missing when things only exist digitally. Maybe I can pass on this iPod as a talisman to an earlier era.

August 29, 2025

Now that I’m back stateside, I’ve continued my search for someone to repair my iPod. I think I’m going to go with a company called MackTechs. They are based in Pennsylvania and repair Apple devices of any vintage. The reviews are good. They send you a box. You send your device. Then they let you know if they can make a repair.

September 15, 2025

After a brief snafu where they had my address listed in New York City instead of Hoboken, my box has arrived. As I slip the iPod in, I notice the capacity engraved on the back: 20 gigabytes. That meant the device held about 5,000 songs. I remember this number being mindbogglingly large when I got my iPod in 4th grade. (If I recall correctly, it was purchased with money my parents had stowed away from when I made my first communion a few years earlier. Thanks, Jesus!)

The iPod’s capacity grew quickly. The first device was billed as holding “1000 songs in your pocket.” In less than a decade, you could spend less money on an iPod that held 40,000 songs.

Of course, this is all dwarfed by streaming. Apple will often bill their streaming service as having 60 million songs. This is a low-end estimate. There are hundreds of millions of songs across the web. Am I happy that I have access to all of that music for a small fee? Yes. But I do often wonder how much more utility I gain with each additional thousand songs that I have access to. As I drop the box containing my iPod off at UPS, I know that I’ll probably never know. But I’ll continue to wonder.

September 30, 2025

It is indeed the drive that is borked. They said they will replace that, along with the headphone jack and battery for $159, shipping included. Could I get this all done for cheaper? Probably. I’m not really upset about the cost, though. I just want to get this thing working. What upsets me is that they won’t be able to save the music on the device. I do still have my iTunes library, but it’s not a snapshot of the time I was using this iPod. It’s from the last time I stopped using iTunes in like 2014. But I guess this is the best we can do.

October 15, 2025

While doing press for my book a few months ago, I was talking to

Taylor Lorenz

. During our conversation, she mentioned the resurgence of iPods among younger people. This struck me as strange. Why would younger people be using a decades-old device when they had the limitlessness of music streaming at their fingertips?

Part of it might be practicality. My boss mentioned to me that his son’s school bans phones. An old iPod is a good way to circumvent that rule. Still, it seems as I search around online that this resurgence is real but focused on something else.

• “Why are Gen Z collecting 20-year-old iPods?” by James FitzGerald (Dazed)

• “Gen Z thinks iPods are cool again” by Millie Giles (Sherwood News)

• “The Resurgence of iPods and MP3 Players” by Andreas Gardner (The Catamount)

• “Why People are Buying iPods Again” by Mike Anguilano (Medium)

• “The resurgence of the iPod: why older mediums are gaining popularity” by Thien Dan Pham (The University Daily Kansan)

Nearly all of the articles, along with a slew of YouTube videos, attest that the iPod’s resurgence is a technological backlash of sorts. “The algorithm failed music,” Terrence O’Brien wrote for The Verge in the last few weeks. People are tired of feeling like their choices are determined by internet platforms. They are tired of having to pay for services every month until the end of time.

I understand this sentiment. A few years ago, I wrote about online nostalgia that I was seeing for the bygone video rental store Blockbuster. In that piece, I argued that people weren’t necessarily nostalgic for Blockbuster but for the “Place Dedicated to a Thing.” Sometimes it was nice to go to a location that was built specifically for video rentals. Now, I can get food, movies, music, and every gadget at the same URL.

iPod nostalgia feels similar. It’s nice to have a thing dedicated to a thing, which in this case means music. When you turn on an iPod, all you have are the songs you’ve loaded up on the device. No social platform can bother you. No person can reach you. It’s just you and your music. Sometimes I want to go back to that.

October 19, 2025

A package has arrived at my apartment from MackTechs. I quickly cut through the packing tape. A load of bubble wrap is inside. As I slowly unwind it, I see my beautiful 4th generation iPod. I plug it into the charger and moments later, it’s alive!

No, there isn’t any music on this thing right now. But I can’t wait to dig through my old collection of MP3s and import a few hundred. Will this likely become my primary mode of listening? Absolutely not. As I note repeatedly in this newsletter, I work for a music streaming service. Independent of the fact that it pays my salary, I like music streaming.

Still, I do think this device will become part of my regular listening habits. But what to listen to first? I’m either going to go with Cindy Lee’s Diamond Jubilee or Bruce Springsteen Live at the Capitol Theater - 9/19/78. Neither of those albums have made it to streaming. For now.

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If you enjoyed this piece, consider ordering my book Uncharted Territory: What Numbers Tell Us about the Biggest Hit Songs and Ourselves. The book chronicles how I listened to every number one hit in history and used what I learned during the journey to write a data-driven history of popular music from 1958 through today.

Should you want to sign a copy, come to Little City Books in Hoboken, New Jersey, on Thursday, December 4. Reserve your spot today!