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The classic 6th Gen iPod was my favorite, up to 160 GB storage.

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Yep, still got my 160GB Silver one. Love it. Tactile clicky controls are still better.
 
iPod mini, hands down was the best as it retained the original DNA while keeping things simple and compact while being functional. Nano is a close second.
 
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As someone already said iPod Nano 6th generation. That squared screen with touch, and that you could even rotate it. Gimmick but it blew me away and I used to show it to colleagues to demonstrate what was achievable at such tiny size. And it counted steps - my first activity monitor.

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Loved the proportions. Still have two of it.

But my first was an iPod Nano 3rd Generation. Loved it, still own it, works as my workshop player. I felt crazy back then to spend “a much money” on a music player but it changed so much for me.

I finally also purchased a classic - one of the last series. Ended up as my music player at work.
 
Probably the 4th gen iPod touch even though I never owned one. I was so jealous because I had the 2nd gen. It sucked back then when the 2nd gen didn’t get multitasking and the full iOS 4 support.
 
The second generation mini. Great battery life and 4 or 6 GB was more than enough storage for most people at the time.
Yep, I remember having to call around for a while trying to find a green 4GB second gen mini. They were always hard to find it seemed.

That was my first iPod and my first Apple product.
 
My favourite was the 5th gen nano, it was perfect in every way. I had the space grey one, I also had the Product red 4th gen but the design of the 5th was just perfection.
I always thought it was such a great final step of the nano's original form factor, plus it was the last gen that didn't remove any features of the previous.
 
iPod touch 2.
It was mind-blowing to have the internet in my hand, read and send emails from that tiny thing, play music and games on it, use it as an alarm clock, watch stuff on it…
I honestly wish I hadn’t sold it back in the day :(
I’ve got a 4th gen now but it’s not my original one and it’s not in as nice a state as that one was when I sold it.
 
My favorite was my original iPhone. It was a widescreen iPod with touch controls. And a revolutionary mobile phone. And a breakthrough internet communications device!
 
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The third gen. I loved the backlit red buttons and the fact they were capacitive

I thought I would be the only one to go for the 3rd Gen. I have a soft spot for it since it was my first iPod. A bit of an oddball in the family, but I still loved it.

iPod Classic series was also great, but I moved on to the iPhone shortly after.
 
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To me it’s a tie between the 6th gen classic (used for my car) and 6th gen nano (used for gym).

However both were rendered obsolete once the iPhone got a decent amount of storage (iPhone 4S with 64GB).
 
I had an iPod touch 3rd gen as my first iOS device. Loved the thing, learned iOS development on it.
Then they broke into my house and stole it, together with my aluminum unibody MacBook, a Titanium PowerBook, and my first tablet, the infamous 1st gen Google Nexus 7 with the emmc that became slower and slower over time (if I knew it, I wouldn't have bought it again), that was my first Android device and learned Android development on.
 
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2 of them:

The very first iPod for getting me into it, god I loved that thing and tried so hard to keep it pristine. Everyone was amazed by how much it held, the quality of songs, etc. Before that my MP3 player held... I think 10 songs. The click wheel was amazing.

The 4th gen shuffle. Super tiny, no need to worry about it. Durable as hell and cheap. No need for screen or little games, album work or any of that other bs. Just music. Give me music I can clip on to my shirt while I run or walk around the house or whatever.
 
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