So I did a slightly mad thing the other day. I bought an 5th Generation Classic iPod in 2026. Yes.. in year 2026, I bought a 20 years old iPod (not exactly but you get the idea).
But then it is not the first time I bought something retro. I did that in 2022 with the last iPod 7th generation. Of course, years ago, I bought other iPods too such as 8GB Apple iPod touch.
Memories….. But I have never ever own a Classic iPod. The ones that were launches years ago.
Table of Contents
Not a new one — Apple stopped making these ages ago. This is the classic 5th generation with the click wheel, same model from about twenty years back. Except mine’s modded: someone swapped the old failing hard drive for a 256GB SSD and dropped in a fresh battery. A 2005 device with a 2026 heart.
Why, when there’s a phone in my pocket that already plays every song ever made?
Why Buy a Classic iPod in 2026 ?
One device, one job
My iPhone 16 Plus is a slot machine. I pick it up to play a song and five minutes later I’m deep in WhatsApp, or checking my IBKR account, or scrolling something I won’t remember. The music was just the excuse.
The iPod can’t do any of that. No apps, no notifications. It plays music and that’s it. Picking it up actually means something now — I’m choosing to listen. In a life with too many tabs open, having one thing that refuses to multitask is strangely peaceful.
The music is actually mine
I’ve spent years building my FLAC collection — ripping, tagging in Mp3tag, getting the album art just right. On the iPod, that’s exactly what plays: my files, my tags, my art. Nothing vanishes because a licensing deal expired. Same reason I run my own Jellyfin server instead of streaming — I’d rather own my stuff than rent it.
That click wheel, man
You forget how good it is until you hold one again. Thumb on the wheel, skip a track, nudge the volume — all by feel, all while it’s in my pocket. Twenty years of touchscreens and honestly nobody’s made anything better for just listening to music. It is just so satisfying……
The mod fixes what was wrong with it
The original iPod’s two weak points were a spinning hard drive that eventually died and a battery that aged out. Mine has neither. SSD means no moving parts and 256GB of space; new battery means it lasts for days. Classic experience, none of the classic headaches.
No regrets
It’s a 20-year-old gadget that, with a couple of upgrades, will probably outlast this year’s flagship phone. It does one thing, does it beautifully, and asks nothing else of me. In a world of devices that always want something from you, there’s a quiet joy in carrying one that just plays your music and shuts up about everything else. Worth it.
The other reason was I was reading this book, Apple: The First 50 Years Kindle Edition by David Pogue and it was such a good book. I read about the iPod history and I guess I got carried away 😉
Why choose 5th Generation iPods instead of 7th Generation iPods ?
But in the internet, you can buy the 5th or 6th or 7th generation iPods today. So why buy the 5th generation iPods.
This video by Garrett Crespo tackles a popular debate among retro tech collectors: Which iPod DAC (Digital-to-Analog Converter) is the best?
According to the creator’s experience working in a recording studio, there is no single “best” DAC. Instead, the right choice entirely depends on the type of headphones you are plugging into the iPod:
The Wolfson DAC (3rd Gen to 5.5 Gen iPods): This DAC has a naturally warmer sound profile [00:15]. This makes it the ideal choice if you are using mid-tier or low-end headphones (like standard Apple earbuds, or basic consumer Sony/Bose headphones). The warmer profile helps bring the bass and mid-tones back into the mix that cheaper headphones typically miss [00:49].
The Cirrus Logic DAC (6th Gen, 7th Gen Classics, and Nanos): This DAC provides a much more accurate, “flat” sound profile [01:12]. While average consumers at the time thought these iPods sounded worse with the cheap included earbuds, this DAC is actually perfect for critical listening. If you use high-end studio reference headphones (like Sennheiser HD600s or Yamahas), you will want the Cirrus Logic DAC for the most accurate sound representation [01:54].
In short: If you use regular everyday headphones, buy an older iPod with the Wolfson DAC. If you use high-end studio headphones, get a newer iPod with the Cirrus Logic DAC!
Unboxing my 5th Generation Classic iPod in 2026
I bought this iPod from eBay and what’s included in the box are as follow….
What’s Included
- Apple iPod Classic Professional Upgrade Edition (whatever that means 🤷)
- Dedicated Charging & Sync Cable (that’s the 30 pin iPod cable)
- Fast Charging Adapter
- High-Fidelity In-Ear Headphones (nay. it is just a pair of headphones)
- Premium Protective Case (not really premium but hey.. not complaining. Go Shoppe and buy something else)
- Tempered Glass Screen Protector
- Microfiber Cleaning Cloth (definitely not Apple Cleaning Cloth)
- User Manual & Warranty Card
Unboxing Photos !!
Hello….
Yes Designed by Apple in California indeed.
Hello iPod classic !
And the 2 cables. The earphones cable and the 30 pin iPod cable.
Beautiful iPod Classic
Yes.. 256GB iPod classic
IN the manual, it mentions that there is a dock connector. I did not find that.
My iPod classic in a “premium” case
Upon switching on the 5th Generation iPods, I find that it was already set up as a Windows iPod. Not going to work as I am using a MacBook Air.
And of course, since I am using a MacBook Air, I would need a converter to connect the 30pins iPod cable to the USB-C port.
Setting up the 5th Generation iPods in 2026
When you plug in the 2005 iPod to your 2026 MacBook Air, you pray. Then it works 🎉
You can see the 5th Generation iPods on the desktop…… nice….
And surprisingly, also in the Music app (yes, remember, there is no more iTunes App in 2026).
You will then set up the iPod in the Music app (to be exact, in the Mac Finder now)…
You can then see this screen….
And that version 1.3 is the latest (or last version)…..
But wait. Dont be in a hurry to sync the music. Do yourself a favour. Do a factory reset of the iPod as it is a Windows iPod (in my case) and I am using a Mac. Or at least just do a factory reset. To do that, just click on the RESTORE iPOD button in the page.
It should take a quick 5-10 minutes.
Dont worry if it takes longer. Just give up 😊. Reboot your MacBook Air without unplugging the 30 pin cable and the iPod.
And then you can now sync your iPod with the Music in the Music app.
Syncing of my Chinese Music Library in progress…
Apparently, my MP3 library is just so small compared to the storage capacity of my iPod. Ha ha. My FLAC library is a different story.
Synching also brings over the playlists on the iPod. Love it !
My Chinese albums on the iPod
My Genres too…
Hello Apple Classic iPod with Album Art Covers
Showing some songs that I have on my iPod with album art covers !
Jay Chou
Leslie Cheung song …
And Tarcy Su in iPod 2026
Conclusion
Another day, another crazy idea of mine. Hopefully this works out and I will be able to take and enjoy the music on my iPod.
How about you ? What are your memories of the iPod ?
And never forget the amazing Steve Jobs introducing the iPod !
