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A CD-based Walkman (which played MP3s in addition to CDs). Despite being slightly larger than a CD, it could still fit in my pocket!
 
5GB 1st gen iPod...2002

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The iPod Nano first generation [1GB] storage capacity was my first MP3 player. It held my massive collection of six albums. It sure did beat carrying around a clunky CD player and the jewel case for all of the CDs.
 
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File:Creative_Nomad_Jukebox_(DAP).jpg


The Nomad Jukebox, and at the time it was the best MP3 player on the market and I will put up against the early iPods. They had 6 gigabyte hard drives but I bought one on eBay that somebody upgraded to a 20 gig. I also owned the follow up nomad jukebox 3.

I was a devoted Creative guy until they came out with the Photo iPod which displayed actual cover art.

If I had to go back I would still favor my creative jukebox over the old greyscale iPod's.

It had line out, you could record at 44.1 KHz, you could listen to music at half speed (helpful for figuring out guitar licks).

I liked how it looked like a portable CD player. Back when I got it everybody was listening to music out of their portable CD players, I had something that looked like a portable CD player only it stored my entire music collection
 
My first MP3 player was a Rio 600 with 32MB of memory.

It was difficult to use, the software to load songs I don't think existed or it was junk (can't remember).

And with only 32MB of memory it was pretty much useless since I couldn't really load that many songs onto it.

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5GB 1st gen iPod...2002

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Same here. I kind of wish I hadn't sold it. On the other hand I'm still using the 2004 click wheel iPod that I replaced it with. Before I got the iPod, this is what I was using as a portable music player (still works fine 14 years later – I even managed to revive the original battery):
 

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Creative MuVo. It was the precursor to the iPod Shuffle. 64MB of memory on a small stick. It was relatively good, but it had an annoying flaw. When the batteries were almost dead, it would stop playing music and suddenly play white noise at a pant-crappingly-loud volume.

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Dell DJ from 2002. Didn't like the software too much or the earphones-though the concept was neat enough.

9 years later I got its replacement, an iPhone 4. :D :apple:
 
iPod Mini

I remember I hemmed and hawed but when the iPod Mini came out for $249 and was compatible with Windows, I jumped at it. It wasn't long after I bought my first mac as well a 12" Mac Laptop
 
My first MP3 player is Diamond multimedia pmp300. 32mb of storage, expandable to 64mb. i loved it very much.
 
Iriver H120

My first "love" was an Iriver. This was an HDD as opposed to most flash players Iriver had at that time. This was one of the first "Ipod killers". That didn't happen, but it was a great device for me. Look at that remote!!! That was sweet!
 

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My first MP3 player was a SanDisk 'Sansa' blah blah...Tho it already had a 30-pin connector, I always thought they were Apple exclusive o_O
My second was luckily the iPod Touch 2G, got it to xmas 2008, I dreamed about getting a Nano and then I got surprised, with something even better... lov it :apple:

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I know it's a little bit dusty but I don't really want to spend any more time w/ it...
He is just chilling in my drawer. Would like to get the charging cable too lol^^
 

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First I used an old Philips 4GB MP3 player. A few months later when I turned 13 I got a 32GB iPod touch 4th gen, and a few months after that I got a 2GB 4th gen shuffle. I am currently 16, my iPod touch fell apart, and I now own a 64GB iPod touch 5 (Black).

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-iPod touch 4th Gen Black (Not my Pic)
-iPod touch 4th Gen Black (32GB, My Pic, Destroyed)
-iPod touch 5th Gen Black (64GB, Not my Pic)
-iPod shuffle 4th Gen Silver (2GB, My Pic)
-Philips MP3 Player Black (4GB, My Pic)
 

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No photos, but my first MP3 player was a portable CD player that played MP3 CDs. About 11 or 12 albums would fit onto one CD, and since it was used in the car, the amount of music was basically unlimited.
 
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