I got my first iPod for Christmas in 2006: a silver, second-generation iPod nano.
It completely changed my life.
But time marches on, and after getting my first smartphone around 2010 (and tragically dropping an iMac G3 on this particular nano), the iPod faded out of my daily life. It’s easy to take Spotify and other streaming services for granted today, but in college I used a VPN to connect to a British server to use Spotify before it was avaialble in the States, and it felt more exciting than using Limewire for the first time1.
Alas, the enshittification curve marches on as well, so starting about ten years ago, I started using Plex to stream my library2. This largely serves my needs. Streaming is undeniably convenient, I have no real allegiance to physical media (or the space it takes up), and multi-room audio streaming is something I deeply appreciate. Self-hosting gives me greater control and stability over my library and I can’t imagine giving that up in a world where capitalism forces every platform to get both worse and more expensive.
The Seed
Maybe your YouTube algorithm is different than mine, but for whatever reason, I couldn’t escape videos of people revisiting iPods, whether in the name of nostalgia or digital minimalism or just in service of The Algorithm for the views.
Interestingly enough, factors converged just enough for this to become a meaningful experiment for me, too.
I’m one of the hold-outs still using Apple’s iPhone Mini form factor in 2026, and I’ve continued to use one since 2020. I overwhelmingly use my phone to stream music and podcasts, but occasionally need it for navigation and communication, which are more important, but less frequent. If I could offload my listening to a dedicated device—especially one modded for large, fast storage and a battery that could feasibly last for days, or even weeks, then I could let my phone’s precious, aging little battery be reserved for tasks like getting me home or messaging.
Since costs shrink with quantity, I decided to buy something like ten of everything, with the intent of keeping one or two for myself and selling the rest to effectively cover the cost of the pursuit.
So I got like ten of ‘em.
Luxury
Turns out, I love having an abundance of iPods.
In a way I hadn’t anticipated at all, I get to be completely and uncharacteristically frivolous, and it’s luxurious. If my iPod dies, I pick up a different iPod. If I need to add a new album to one album, I can plug my headphones into another one while I’m waiting on the first to finish syncing. I can pack two in my bag and just listen to whichever one suits me.
This also helps with analysis paralysis
Another problem with a large library: choosing what to listen to is tough! Analysis paralysis comes into play here, and if I don’t have something in mind, I could do a lot of scrolling before I settle on something. Either that, or I stick to my “Recently Added” section, or randomize my albums. By having several iPods and each curated to a different mood or theme, then scrolling through 50-200 artists is a breeze compared to thousands.
It turns out, this is also what Robert Smith of The Cure does.
[Robert Smith, Baby Driver]
Either the headphones will die or the phone will die, and I need to charge one or the other or both. If I have multiple iPods, when one dies, I put it on a charger and get another. It’s luxurious thinking in abundance like this.
There was at least some blink-182 on nearly every single one.
For better or worse, I love Edgar Wright’s 2017 film, Baby Driver.
iPod Historian
As an unintended slice of the hobby, I got to be an archaeologist or historian and get a feel for the previous owners of each device and their taste. What was the last song someone listened to before this went into a drawer? How many years ago was that? What’s the first song I played after bringing it up?
Some people are very singles-focused, and they have thousands of artists with one or two tracks of each.3
Others gravitated towards compilations, greatest hits records, and Christmas albums. Monster Ballads: Platinum Edition, 20th Century Masters, 37 variants of Very Best Of or The Very Best Of, and even more variants of The Ultimate Collection, Greatest Hits, etc.
One sad example was some mainstream country music, diet podcasts, and episodes of Fox News shows.
The playlists people curated were full of personality, too! On Chris’s iPod, there were playlists like “Emily Mix”, “grad school”, and “Road Trip!” which is enough to tell a story in itself.
Megan’s iPod had playlists for “Guitar Hero II soundtrack” and “Across The Universe!!!!”
Smashing Pumpkins, The Smashing Pumpkins, the smashing pumpkins, blink-182, blink 182, Blink 182, Blink-182, Jay-Z feat… JAY-Z feat…, Various Artists
cartman, terrance and phillip
Dane Cook
Give iPods to friends.
Different iPods for different moods a la Robert Smith
Recommending one.
The consensus is that the 5th generation iPod—the iPod Video, is the one to seek out. It’s attractive, it’s easy to take apart, and it’s easy to repair and upgrade.
I bought one that was “untested,” (oops, it doesn’t work) and I needed to do some troubleshooting or use it for parts. With enough digging, I found a solution involving desoldering a particular chip and placing a solder bridge on the board. I’m not afraid of soldering, but using a hobbyist soldering iron on a board that really requires a micro-soldering setup is basically resigning yourself to luck. But eventually, I lucked out, and managed to get the correct pins bridged. This victory meant a lot to me.
This also means it’s tougher to get your hands on. I also ended up with a pile of 4th-generation models, both the “monochrome” variant with a black-and-white screen and the upgraded iPod Photo variant. This doesn’t accept a massive battery as readily as the 5th generation model, but its batteries are easy to come by and it’s easy to mod with a flash card, which also eases the burden on the battery and makes the device lighter. I bought some lead tape to offset that, but found that I kind of grew to like the weight improvements.
On Star Trek, they have PADDs all over tables. Unlike the deeply personal devices of our world, these are much more utilitarian, more like a pile of inexpensive kindles that can be loaded with reports and can also access information. And I kind of get it.
I’m becoming comfortable with the idea that there’s a joy in allowing hardware to serve specific purposes.
I have one iPod that only has music from the past year on it. I have another with the music I’ve been gravitating towards, which usually changes season to season. I have another one that I’ve been using exclusively for all the music I’ve been using for my Dungeons and Dragons game. I just leave it in my DM kit or have it next to my stereo. I have one with classics that tend to get overlooked or ignored in the rest of my library. One with jazz and classical.
I love them. I love them so much I start looking at similar MP3 player alternatives for 2026, and they’re all universally making trade-offs that I don’t want to make. I don’t want a touchscreen. Even with the niche audiophile market for direct audio players (DAPs), there’s nothing appealing enough for me right now. I don’t want to run Android. I don’t want a touchscreen at all. And on the other end of the market, I don’t want a clumsy way of scrolling through files or cheap-feeling hardware.
The reality is that the iPod from two decades ago is a solved design problem. Apple’s industrial design is second-to-none. They perfected a product and had the scale to democratize it to become a cultural icon. There’s such a passionate hobbyist fanbase now that it’s only gotten better! Massive batteries and flash storage upgrades means I can listen longer, store huge amounts of music, swap parts that break, and even do it all myself with a pry tool and small phillips-head screwdriver.
There may be some nice-to-haves:
- An A1 chip with native AirPods support would be nice, but honestly, my IEMs are better anyway.
- USB-C charging and/or magsafe charging would be extremely convenient
- I’m using an old version of iTunes on a Windows gaming PC with my library pulling from a network drive that hosts my Plex media library. Using Finder is a pain, and there aren’t really any good native options for Linux these days.
- Very grateful for LegacyScrobble, but last.fm support returning would be lovely
- I haven’t found a RockBox theme that I like and I think the iPod software is good and attractive. Sometimes I kind of want to bring over more of the 4th-generation monochrome aesthetics with smoother type, though. I think the photo and video screens are big improvements, but sometimes you’re just not in the mood for the aqua theme, and after spending a lot of time tuning my Linux desktop environment, I wish I could make a couple of adjustments to my iPhone theme as well. Again, eventually I may write some changes into a RockBox theme, but not today.
I don’t like Spotify playlists. Mixtapes were magic. Mix CDs were my era. But today, I can loan a crush a whole iPod with songs, let her play it until it dies, and then give it back aftewards4