Background information
50 years of Apple
by Samuel Buchmann
iPod nostalgia: romanticising the past
9/4/2026
Translation: Patrik Stainbrook
Pictures: Florian Bodoky
In days past, the iPod was pure magic, with thousands of songs in your pocket. But looking back at the details dispels the myth of a perfect past – at least partially.
Even though my 16-year-old PC-nerd self would be kicking himself for saying this, I have to admit one thing: the iPod was revolutionary. It shaped the way we listen to music today. Streaming was still a long way off, yet it was the first mobile device that didn’t require a physical medium to listen to music. No need to insert or swap out discs, which would always skip right when my favourite track came on anyway. And: no anti-skip! Let’s be honest here, it never really worked anyway.
Returning to the iPod, it was amazing that thousands of tracks could fit onto this sleek, compact device and that the whole thing worked with just the push of a button.
This article is part of our series celebrating Apple’s 50th anniversary. You can find the list of all articles here:
A bulky, hulking behemoth
2026 delivers a reality check. I do tend to remember the iPod as almost magical in many ways – a romanticised view of the past. I realise this as I take a closer look at it now, more than 20 years later, on the occasion of Apple’s 50th anniversary.
First, the supposed elegance. My own iPod unfortunately met its demise already, which is why I went on a special hunt for a new one on Ricardo, Tutti and other secondhand sites just for this article. I successfully located my target, but oh no! What’s this? A white brick, two and a half centimetres thick and weighing almost 220 grammes meets my eye. A block with sharp edges that nearly cost me a toenail while unpacking (and dropping) it. Elegant, as if.
But if, like me, you spent years traipsing across town with a Discman, it sure felt like a massive facelift. Still, the specs on the back promise 20 gigabytes of storage. Storage was still reasonably affordable back then, and there was no sign of a crisis on the horizon. And the blank media levy on MP3 players was only introduced by Suisa in 2007 (article in German).
Downloading music – a tragedy in three acts
The Ricardo vendor I bought from didn’t include headphones with the iPod. Some people would already struggle here these days: there’s no Bluetooth. Luckily, I can choose from my extensive collection of headphones. And yes, you still have to turn on most modern headphones – even after you plug them in with an audio cable. Still, all I had to do was plug the cable into the headphone jack and turn on the iPod. At least the Sony WH-1000 XM6 works fine here.
And presto, I return to the past. I run my thumb over the Click Wheel, and that familiar feeling comes flooding back. These days, that soft clicking sound would be called «oddly satisfying.» I look forward to adding my playlists to it and – since there isn’t much to choose from – escaping decision fatigue.
Luckily, I still have my old external hard drive, which has been gathering dust in a drawer for years. There, I find a few hundred MP3 files I downloaded via the legal grey area of P2P networks and ripped from my CDs, all neatly digitised.
Act 1: the hardware
But just as I’m about to pat myself on the back for getting my headphones and music ready, the second shock hits. What’s that next to the headphone jack? A FireWire port! I slowly start to suspect that I underestimated how difficult this iPod music session would be.
Luckily, the seller on Ricardo was kind enough to include a FireWire cable. However, I no longer own a computer with a FireWire port.
This calls for a massive daisy chain of adapters. I own a Mac Mini and a MacBook Air, both with an M-series processor. So, I need an adapter that downgrades Thunderbolt 3 to Thunderbolt 2. I acquire a Thunderbolt-to-FireWire adapter as well. Next, I have to connect the FireWire cable that came with the device. Alright, this’ll work – probably. No guarantees. Fine, I’ll just go with Windows. I’m going to buy a PCI Express FireWire card and install it in my PC.
That’s a real hassle too, and despite my IT background – I did a computer science apprenticeship ages ago – it’s a never-ending struggle with my shaky hands. I turn on the computer, run a gazillion Windows updates, and – wow! – the card’s recognised right away. I’m briefly tempted to pat myself on the back again. But I know better now. I carefully plug in my iPod.
Act 2: the software
Now I need iTunes. It’s no longer available on Mac, and even though it’s still on Windows, it’s been slapped with legacy status.
On top of that, I need an older version of iTunes to get the iPod to work properly. Ironically, I find plenty of old versions of Apple software online – for Windows. I can’t find anything useful on macOS Tahoe. Mind you, getting it to run stably would be a gamble anyway.
I install version 10.7 of iTunes. It was released in 2012, and is the most up-to-date version of the program supposedly still capable of running reliably on my 25-year-old iPod – on top of supporting 64-bit architecture. Still, this is unofficial information. But happily, the iPod is recognised! Unfortunately, right after this triumph, I realise why I usually preferred Creative’s Zen series to the iPod as an MP3 player. iTunes crashes as I try to import my music library. Still, it works after a few tries.
And here comes the next gut punch. After all these years, I can’t remember exactly which track or album I got from which source. Still, at least I know which songs came from the internet and which ones I ripped myself. I actually named the latter files clearly and structured them logically, exactly the way I’d like them to be – but only the file names. iTunes ignores those. There, songs are listed as Track 1, Track 2 and Track 3 by Unknown Artist. The thing is, I never added any ID3 tags. With the drag-and-drop system on other MP3 players, this wasn’t necessary. After an import, that system simply displayed file names on-screen. I try it in Windows Media Player, also outdated. However, I encounter the same problem. And, of course, you can’t look up album information using legacy software any more. Uuaarrgh! (That’s my exasperated outburst – as well as the album title that’s meant to be there.)
Act 3: disappointment following euphoria
I calm myself and start putting together playlists. Not just quickly thrown together, mind you, actually constructed. I sort through songs, rearrange the order and think about which track makes sense where. It takes less than ten minutes for me to slip back into that old mindset: a playlist isn’t just a collection of songs, but a sequence with a narrative arc. I catch myself swapping out a song because it «comes too early» and moving another one back because it needs more space.
Maybe I do this because everything here takes a little more effort. You can’t rely on iTunes. For example, I can’t create a genre playlist because a) some of the ID tags are missing and b) iTunes has its own ideas about which songs belong to which genre. For example, individual MP3 chapters of a kids’ radio play end up in the German rap genre. Well, at least German is correct. But even though the whole thing is a bit of a struggle, I’m chuffed to have created something. Without an algorithm suggesting anything at that. And without an endless array of choices overwhelming instead of inspiring me. It’s simply a limited collection I go through.
I click Sync and put away my iPod. But wait. One of my seven playlists is missing. Damn, I probably didn’t choose the right ones. Once again, I reconnect the iPod and sync, then I leave the house with it by my side. I sit down at the bus stop and turn on my iPod. The block starts to hum and vibrate slightly. That’s from the 2.5-inch hard drive inside the case, which is now accessing my playlists. Yep, you read that right. Hard drive. HDD. Turns out you can’t do without a mechanical medium after all.
But wait – did I say playlists? In fact, I only find the one playlist that I supposedly resynced. Apparently, it wasn’t added but replaced the others. Even though I haven’t used an iPod in 20 years, this problem still feels familiar. iTunes, you tricksy minx! Still, I enjoy the bus ride with the playlist I made. And next time, I’ll bring my iPhone and the streaming app – after all, they’re popular for a reason.
Header image: Florian Bodoky
I've been tinkering with digital networks ever since I found out how to activate both telephone channels on the ISDN card for greater bandwidth. As for the analogue variety, I've been doing that since I learned to talk. Though Winterthur is my adoptive home city, my heart still bleeds red and blue.
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