Hot take: Apple Music on iOS and macOS sucks. The iPhone has never really been the best way for me to consume music—and yet, for the past 12+ years, it’s been the device on which I’ve listened to music.
Ever since OS X came out in 2001, I’ve been an unrepentant (and maybe irrational at times?) Apple fanboy. In my eyes, Apple could do no wrong—for years. At the time, I was in the early days of my college career and had no way of affording a Mac. I would have died to have a PowerBook G4 or a Power Mac G5. Instead, I did the next best thing: I skinned my Windows XP operating system to mimic OS X and found a PC case that looked close enough to the Power Mac G5 to pass at a glance.
When the iPod came out, I looked on with envy at the few people I knew who had a Mac and could afford that mind-blowing music player. I settled for cheaper (usually) options from other manufacturers, with the old Sony MiniDisc Walkman being the last one. Bought on a bit of an impulse, it was not one of the better decisions I made around early 2004. I used that device through the summer, listening to music at the top of the C.O.P.E. tower at Island Park Scout Camp while younger Scouts climbed and rappelled to and from the top.
At the beginning of the fall semester, I took almost all of what I’d earned that summer and went to the BYU–Idaho campus bookstore to buy my first iPod: a 4th Generation (later known as the iPod Classic) with 20 GB of storage. At the time, I thought there was no way I’d ever fill it up. Here we are in 2026, with my library taking up somewhere around ten times that amount.
I was still running a Windows machine—still skinned, and still dealing with the weird glitches that came with making Windows look and behave like a Mac—but iTunes had been available on Windows for a couple of years by then. From virtually day one, it was my preferred media player.
I don’t remember how long I used that first iPod, but I know that over the years I had at least three different ones: the 4th Gen, a 5th Gen (pretty sure it was the first revision, not what later became known as the 5.5th Gen), and a 6th/7th Gen (there was no official 7th Gen—just a later version of the 6th with higher storage options).
Those iPods were always with me, piping music or podcasts into my ears at nearly all times of the day—through headphones, earbuds, or my car stereo. That is, until a fateful day in November of 2013.
I had gone down to Salt Lake City to see Iron & Wine play at In The Venue. At the time, I was living in Logan, Utah, and driving a 1994 Toyota 4Runner that was nearing the end of its life. I usually rented a car to get anywhere outside of Cache Valley. I must have forgotten to lock the doors that evening. I remember having a nagging feeling throughout the concert that I’d forgotten something.
When I got back to the car, my iPod was gone.
I was devastated.
Not being able to afford to replace it—or choosing not to make it a huge priority—I was more or less forced into using my phone as my primary media player. Though, now that I think about it, that fall may have been when I briefly went over to the Dark Side and used an Android device.
I’d had an iPhone since its original release day, and aside from that brief foray into Android, I’ve been an iPhone user ever since. But never—not in those early days, not after my iPod was stolen, and not even now—have I felt that the iPhone’s music player was particularly great.
There was nothing wrong with the audio quality, but I’ve always had issues with how music is organized and sorted on the iPhone. I immediately felt a loss of connection with my music library when I had to start using it, though that loss is still difficult for me to describe.
There were differences in how certain playlists were sequenced compared to how I’d set them up in iTunes (and later Apple Music) on the desktop. Despite having some control over sorting on the phone, I could never quite get things to match. Another complaint I had was the on-screen display of the song title, artist, and album. I grew to like the way the iPod presented that information and just couldn’t—still can’t—get over the difference.
I shared many users’ feelings that iTunes, in its later years, had suffered from a lot of bloat. It tried to manage music, podcasts, TV shows, and movies all at once. So while I was sad to see iTunes go away in 2019, I was also excited to see Apple replace it with separate Music, Podcasts, and TV apps on the phone, iPad, and desktop.
At first, it felt like the right move. And for a while, I really enjoyed the experience of each app.
I know that contradicts some of what I’ve said about the iOS Music app, and maybe I’ve made it sound like I hated it entirely. I didn’t. The app has plenty of virtues: I like being able to create and edit playlists on the fly, set up a queue, and easily toggle shuffle—something that was admittedly clunky with a click wheel. And, of course, there was the luxury of streaming nearly any song ever recorded (availability notwithstanding).
But after several years of having that luxury, I slowly—and unknowingly—grew further out of touch with my music library. I added entire discographies simply because they were there. Over time, I created a lot of bloat of my own. I eventually realized that there were many songs and albums in my library that I couldn’t remember where, when, or why I’d added them. That began to really annoy me.
Conversely—and perhaps more frustratingly—I’d often get a song stuck in my head and struggle to remember who made it or where it came from.
A few years ago, I started longing for my old iPod Classic. I wanted to return to the music experience that had accompanied my early adulthood. If you haven’t picked up on this from other blog posts, I’m a nostalgic person, and there’s nothing quite like an old song to stir those feelings.
I began watching eBay and Facebook Marketplace, and eventually found a 7th Gen iPod for a decent price. I bought it with plans to switch back completely—or at least mostly—to the now somewhat antiquated device.
Somewhere along the way, I learned about the iPod modding community. People were swapping faceplates and backs for colors Apple never made, upgrading storage with SD cards or SATA drives, and even adding built-in Bluetooth. After researching my options, I settled on upgrading the faceplate and back, and replacing the old hard drive with an SD card and adapter.
I gradually bought the parts and tools I needed. Earlier this month, I purchased the final piece—the SD card adapter from iFlash. Last Tuesday, after it arrived, I made the swap when I got home from work.
At this point, I should backtrack a bit. Over the past year or two, I’ve grown increasingly unimpressed with the desktop Music app. Not to the point of outright dislike, but for all of iTunes’ faults, the current Music app seems to have issues of its own.
When Apple retired iTunes, they moved management of older iPods into Finder. When I connected my newly purchased iPod to my Mac Studio, the two just didn’t get along. I constantly had to reset the device, erase it, and reload my music. It was a pain.
Last fall, I started watching for a cheap Windows laptop to see if things might work better with iTunes. After finding one, I discovered that the old iPod and iTunes still play very nicely together.
So last week, after finishing the hardware upgrade, I connected the iPod to iTunes. After restoring and reformatting it, my entire music library began syncing to the new 512 GB SD card inside. (Can I just say how backwards it feels to need a Windows machine to make an Apple device realize its potential?)
As of this writing, I’ve been a few days back in the old iPod world—wired headphones and all—and I couldn’t be happier. I love hearing the familiar click while scrolling through menus. I love seeing the information displayed the way I remember from nearly fifteen years ago.
I miss being able to check my watch to skip a song, see what’s playing, or adjust the volume—but those are minor losses. It’s taken me over twelve years to replace my old iPod, and things feel complete. Like an old best friend I’d lost touch with suddenly reappeared in my life.
And like reconnecting with an old friend, you spend some time catching up and getting reacquainted. My new iPod and I are doing exactly that.
I have far more music now than I did in 2013 when my original iPod was so callously taken. I sometimes wonder if whoever stole it ever listened to anything on it—if they scrolled through my library at all—or if they rushed straight to the nearest pawn shop to sell it for a quick buck and their next meal.
With upgraded storage, this iPod has room for a lot more music in the future. And now, if you don’t mind, I’m going to get back to spinning the click wheel to find some lost and forgotten song.