Of iPods and portable music · g/ianguid/o.today
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Of iPods and portable music

I prefer listening to music files not because of extreme audiophile beliefs, rather every single music streaming service out there suck in some way:

  • Apple Music lags, crashes and glitches
  • Spotify resembles a poorly-written social media website
  • Deezer has probably the worst UX I’ve ever seen

Alternatives are available, but to be completely honest I just don’t care about them: their pricing is either non-competitive or they exhibit the same flaws I just described.

Being an Apple One subscriber I still use Apple Music in the car and to discover new artists, but the bulk of my listening happens outside the streaming realm.

My library is almost completely made of lossless FLAC files — they satisfy my inner data hoarder needs, and sometimes it they also deliver better quality than your run-of-the-mill lossy encoding.

One of the consequences of this choice is that accessing my library on the go becomes substantially harder.

Being almost in my 30’s, I did what every sane nerd would’ve done and bought a couple of used iPods: a Mini 2nd generation, and a 30GB Classic 5th generation.

I spent some time with both, listening to music and tinkering to make them usable in the 2020’s: this is my adventure.

The Mini #

Ever since I laid my eyes on an iPod Mini at the tender age of 12, I fell in love with its aesthetics — the fact that all the cool guys in my social circle had one didn’t help either.

I bought a second-hand specimen on eBay for about 30 Euros.

My desire was a device that allowed me to disconnect during exercise, walks or in the middle of home chores, while also being a cute piece of nerd kit.

Imagine pulling tricks on your bike with an iPod Mini in your pocket blasting your favorite emo tunes, so 2000’s!

I dug into the r/iPod Discord server and started chatting with the fine folks over there.

This is the action plan that followed:

  • replace the internal HDD with a CompactFlash of adequate size
  • clean it up a little
  • convert most of my library to AAC
  • enjoy music

After trying some CompactFlash to SD/microSD adapters as well as cheap CF cards, I figured I had to stop wasting my time and got a good quality SanDisk Extreme in the 64GB variant.

Then a dramatic series of events happened: I snapped the ClickWheel flex cable in half and had to buy a replacement off AliExpress, and after that the battery swelled so much the internals started cracking under its pressure.

I loved the black and white 2000’s aesthetics of that screen: Mini, you will be missed.

RIP o’ Mini fella 🥲

The Classic #

Having to convert, copy and pray 64GB of space are enough each time you want a new album on-the-go was one of the main drawbacks of the Mini.

Sure, you can fit up to 128GB of CompactFlash memory on a second generation Mini motherboard, but eventually it’ll fill up and you’ll be left with a hard decision to make: what album goes and what stays?

For my next iPod iteration I went for a model which could fit much bigger microSDs and batteries, with parts available cheaply and more often than not being shipped from the EU: the 5th generation iPod Classic.

Once again, eBay helped with the discovery of a used but in great shape 30GB model for as little as 30 Euros.


Classic models support up to 1TB worth of microSDs thanks to the amazing work of iFlash.xyz , so I decided to go with a 512GB card and a iFlash Quad for a grand total of about 110 Euros shipping included.

EliteObsolete Electronics sells high-quality replacement parts and batteries for Classics, and that’s where I got a genuine LG 3000mAh battery for a device that has been discontinued for years now — it’s crazy and amazing at the same time!

Running Rockbox and having all that disk space in such a small package allowed me to execute on the simplest synchronization program that ever was: copy-pasting music.

No more AAC conversions, yay!

My “workbench” during the modding procedure.

Life after iPods #

How’s the Classic doing nowadays?

Great! But planning on selling it.

After a while I noticed the device isn’t a good fit:

  • the power design of the 5th generation iPod is too simple, my IEMs are too sensitive and end up catching all of the resulting noise
  • the USB stack and disk are too slow, syncing 120GB worth of music took about half a day
  • Rockbox isn’t really user-friendly on the ClickWheel once you try to use it for real
  • some of the albums I own are encoded in a bitrate or bit depth which is too difficult for the iPod’s CPU to decode in real-time

While I love the look and feel of 2000’s Apple products, I came to the conclusion that iPods are too dated for my needs even with upgrades like flash disks and new batteries.

While they’re probably the better alternative to streaming services for anybody in need of a digital detox1, if you have particular needs or have a library composed of exotic encodings they’re probably not a perfect fit.

One can work around those issues, but is it worth it?

For me listening to music should be the most plug-and-play experience possible: no AirPods auto-pairing shenanigans, no headphone battery at 0%, no social +1’s or likes, and especially no keeping a copy of the same library in a slightly different bitrate.

In the end I fell back on a base model Sony Walkman plus a custom firmware that enhances the user experience and apparently audio quality by borrowing software bits from its bigger brothers.

Apart for the proprietary WMPort connector — which has been replaced in newer revisions — the device is fast enough to handle my multi-GB music library and its various funky audio formats, sounds great with my high-sensitivity IEMs2 and supports drag-and-drop copying.

Battery life is great, has a microSD slot as well as 16GB of internal storage — which I never use — and if I’ll ever end up needing Bluetooth headphones again I can use them!

I do have some gripes: why did Sony engineers thought releasing a music player without a “play next” button was a good idea?

Also, why oh why does this thing need to rebuild its file index on every reboot?3

Admittedly, Walkman design language speaks to me a lot.

  1. Or came to hate how music is mistreated in recent years! ↩︎

  2. Even though the review I linked says otherwise. Weird? ↩︎

  3. A little voice inside my head pushes for a good old session of reverse engineering, accompanied by lots of swearing and a maybe faster boot times. ↩︎