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1st gen iPod from 2001. Still have it, and it still works. I put a new battery in it a couple years ago and got it a 20gb Hd instead of its original 5gb.
 
iPod Nano, 2007 my fav non mac apple product still works this minute!
photo.JPG
 
I think its an iPod Shuffle, before i had a Sony Walkman or CD player, so vintage but it wasn't too odd at this time
iPod Shuffle, so tiny, i loved it
I may buy stuff like that again if they release an iPod Shuffle again, lets imagine an iPod Shuffle + Airpods Pro 😍
 
From the Ipod, my first was the 2nd generation, I bought it with a broken tach, but it still worked fine.
 
I started off with a Diamond Rio 500. Back then I ripped all my music in 96kbps to maximize the amount of music I could fit on the player. I still have a few mp3s in my library at 96kbps. In 2002, I upgraded to the original 5GB iPod.
 
A Samsung clone with a meager amount of storage. Would have been sometime around 1996 I think? Looked very similar to this.

First I had a CD Walkman.

Then I had something very similar to this, around 2002 though. I could only store like 20 tunes on it lol.

Then I had the white iPod Nano 1st Gen and now I have my iPod Classic.
 
My first was the Creative Zen xtra - 60gb in 2003 or so. It was incredible to be able to take all my music with me. I loved the huge screen too!
 

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iPod 4th generation. As I’ve said elsewhere on these forums, it’s still my favourite Apple product as I was so excited about being able to take my entire music collection on holiday with me, in something the size of a cigarette packet.
 
iPod 2nd generation - and I used it with Windows before iTunes for Windows was a thing. The software that came with it was horrible.
 
I began with MD players and dubbed MP3s on laods of disks. Then in 2005 or 6 I picked up a 4th gen iPod. I've recently gone back to MD.
 
My first was a weird Samsung phone (T-809 if memory serves).

It was a slick looking slider with a awesome display for its time. The sound was absolutely terrible.
 
I've also owned the HipZip by Iomega when they were trying get people to like their Clik disk format.

Jul05-MP3-Fig4.jpg

The HipZip was my first one! Before that I burned CDs for my regular CD player or recorded the music onto MiniDisc. The cost of Flash storage didn't make sense to me.

Funny story... I went to Macworld SF 2001 and I took it with me. When I got to the Iomega booth they were so surprised to see someone with one that they gave me about 20 Clik disks for free. I used that for a year before the iPod came out. Kinda wish I still had it, but I don't even use the mint iPod classic I have.
 
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