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As much as I loved the early iPod and iTunes, it was really was the beginning of the end of not appreciating each song. 1000's of songs … too easy to skip around and such. We're just not a contemplative society as much and I'd not be surprised if iTunes was a major contributor.
 
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My first one... the student package got me hooked with my first Apple purchases in 2003, almost two decades ago. I vividly remember it: a 12" Powerbook G4 867 MHz, a 3rd generation iPod, a Canon printer, and if I remember correctly, .Mac. Such a sentimental time in my life... forgive the length it adds to the post, but I even included it as the introduction to my most favorite graduate school paper:


At the beginning of 2003, I used my new college student discount to buy an education bundle that included a laptop and something in a new category of devices called an iPod. In the slow and dead hours of third shift, I used my time to learn an entirely new operating system and work on college assignments. In the calmness of the midnight hours, I would listen to sermons on my iPod as I walked outside around the Ryobi property. At the beginning of 2004, some people in church donated some money so that I could start a 15-minute weekly program at our local AM radio station. In hindsight, it probably wasn’t the wisest thing to do: to give a new Christian attending a fundamentalist college a voice to say whatever was on his mind across the airwaves every Friday at 5pm. It wasn’t much, but it was what I had, and I wanted to give it to God. I read in a technology magazine about a new way people could download MP3 files on demand using RSS feeds called “podcasting.” The radio programs were already in MP3 format when I recorded them, so I used a template and taught myself the bare basics of writing an RSS file and creating a podcast in 2005. I was fascinated, absolutely filled with child-like wonder.

So at the beginning of 2005, alone at work in the middle of the night, I could listen to sermons from a pastor in Florida while walking under the stars. I could read the Bible and search for words in MacSword. With a microphone and SoundStudio, this little kid on nightshift could talk about the Bible. And with an RSS file with MP3 attachments, people beyond the AM radio signal could listen if they wanted to—the family in Indiana who blessed us with a gift for our marriage, the mother who recently miscarried in Wisconsin, the mother raising three children in West Virginia, the man in Oregon who donated web server space, and a pastor in Fresno… maybe the format was so new that the options were pretty limited. But like the lad with the fish and the loaves, I gave to Jesus what I had—a love for him and a desire to use technology for him—and he blessed it.

It was my feeble attempt to get in on what seemed to be a revolution in how digital media was being delivered and consumed. Life was simple, technology was changing, the spare room in our apartment was my computer room, and I had little knowledge of the Bible and little knowledge of how computers actually worked. Eventually, the local radio station closed, the podcast stopped, life got busy, and the handful of people who subscribed no longer heard me 15 minutes a week—the USB mic I bought for the radio program has been idly stashed in my desk drawer for nearly a decade.

I obviously didn’t change the world, but a new love for Jesus and an interest in technologies for the new millennium changed me. And without even realizing it, I think it was Jesus teaching me that I can find his fingerprints everywhere—even in operating systems, beautifully designed electronics, RSS and XML feeds, website design software, MP3 sermons, and an email folder to keep correspondence with people who told me thank you and to keep going.

Spiritually and technologically, it is the most sentimental time of my life. This paper, written as an assignment in biblical theology, will surely not start any academic flames. But, perhaps God can use it to rekindle the spark of wonder I had years ago, that he cares about how we might live all parts of our life for his glory. For those who think it may be too technological and less biblical, I’ll blame that on my lack of biblical knowledge—I can’t even read the Greek or Hebrew behind our beautifully typeset English Bibles. For those who think it may be too biblical and not enough bits and bytes, I’ll blame that on my lack of technological knowledge—I have no understanding of the code behind our beautiful graphical user interfaces. And if anyone wonders why someone with little understanding of both the Bible and technology wants to write something about how both come together, that is because I never want to lose my child-like sense of wonder as I wander through this world marveling at all the ways the Creator has interwoven doctrine and data, theology and technology in such beautiful, biblical, and innovative ways.
 
Nostalgia dictates that my first iPod (and first  product) the 5th generation iPod nano was my favorite. It was my first embrace of digital music back on my Windows Vista PC. I had the silver model with the black click wheel. I still remember putting off my homework that night to load up all my music and playing with cover flow.

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Honorable mention is the 4th generation iPod touch. I got that a bit later and had some good times. The classic iOS games were a blast at the time and I felt so cool.
 
I miss the iPod nano version 7, mine went "missing" during a move. All they had to do was add wifi to it and it would have been able to remain compatible with Apple Music and be the perfect all around music and small messaging device, using AirPods for voice entry. Sigh.
 

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I never owned one, mostly because (like Jobs) I have always been a physical media kind of guy, be it vinyl or CD. But I wish I would have at least gotten a first generation iPod now, if not just for the collectability of the thing.
 
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iPod Touch gen 2 (the first metal back one one with the speaker, I think released in 2009 or 2010). I still use it everyday.
 
The original iPod Touch is what got me hooked into the Apple ecosystem. I know it hasn’t sold well in years, but I think it still had a unique use (for people who wanted an iPhone without a mobile plan) and wish Apple had kept it alive.
 
My favorite iPod was the nano, specifically, the 4th and the 5th gen iPod nano.

4th gen nano:

View attachment 2003412

5th gen nano:

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I've still got a 7th gen Nano, and still occasionally use it. Not sure if I'm jealous of the wheel of the 5th gen or not, I'm pretty sure all those controls are in the side buttons. Plus it has a multi-touch screen and bluetooth. I don't think they ditched the wheel for no reason.
 
The original with firewire connection- was that a whopping 5GB??? WOW! WOW! WOW! How will I ever fill 5GB? ;)- was THE device that brought me to Mac... soon leading to an insane $2999 outlay for a Power Mac G4. Talk about halo effect!

However, the best one IMO is the one still in active use- approx 5th gen classic. Huge storage inside could actually hold ALL of my favorite songs "in my pocket" at 256kbps AAC. Long after it seemed mostly retired, a new car purchase came with an option to connect to a variety of proprietary jacks and one of those was the old 30 pin. I dug out that iPod, charged it up, powered it to be sure it could turn on, loaded it with all my best playlists, hid it deep in the car and now a great wealth of favorite music selections are always available, commercial-free, no need for cellular data burn or subscriptions, etc.

The stock radio in that car pretty much presents a classic iPod-like interface in the dash and even shows album art while a song plays. Shuffle, playlists, search, etc are all available, even with voice commands. I hope it can keep on being my customized, mobile jukebox in my (car's) pocket for years to come. If not, I've got a generally-retired iPod Touch waiting in the wings to be resurrected and take over that same, singular job if needed.

Count me among very likely buyers if Apple had decided (or still does) to create a one-off 2Xth anniversary edition iPod regardless of the ability to play music from iPad or iPhone. I'd still love a gigantic storage, dedicated iPod in my own mix.
 
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I've still got a 7th gen Nano, and still occasionally use it. Not sure if I'm jealous of the wheel of the 5th gen or not, I'm pretty sure all those controls are in the side buttons. Plus it has a multi-touch screen and bluetooth. I don't think they ditched the wheel for no reason.

You’re right, the 7th gen Nano was a great device, a family member of mine had one for many years and I advised her to replace her aging battery before it was considered vintage. Yeah, and possibly with WiFi could have been an awesome Apple Music device as well, like @nkgmd said above.

However, I think after the discontinuation of the last iPod, the touch (which is an iPhone without celular), I think we’re speaking from our hearts, and back in 2008 the 4th gen nano was the MP3 player of our dreams for many of us. And also they gifted them with the Back To School promo after purchasing a mac.

What I mean is, yes, the last nano was objectively better in many regards, but when talking about our personal preferences, nostalgia plays a big role, and if I had to choose a vintage device to buy in order to keep and look at -and use it, why not?- I’d probably choose a 5th gen iPod nano, just like others prefer the iPod Classic with the big click-wheel, or the iPod Photo, or the iPod Video.
 
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