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Rolls Royce of MP3 players ~1999
Replaced by an iPod v1 in 2001 and never looked back.
 
I first bought a 2G Coby mp3 player that was powered by a AA battery and had excellent sound despite being a cheapy plastic thing. I think I bought it right before I was given an iPod 2nd generation Nano, also a 2G, as a gift.

I still use a newer Coby mp3 player in the office and as a knock-around player. For the money, Cobys still has good sound - at least to my ears. Their players look like plastic toys but honestly their cases and buttons haven't broken on me yet. During the summer mine stays in the hot car sometimes. :( The battery is still going strong, sound is still quite acceptable.
 
Mine was a 1GB first gen iPod shuffle. I was about nine years old then and it was the envy of all my freinds with their Coby and Panasonic MP3 players. I have since owned 5 iPods with my most current one being the 5g touch. Apple's marketing strategy has worked wonders :)
 
1st gen iPod shuffle 512 mb. It replaced a well-loved Sony Walkman CD player. I need to find that Shuffle and display it. Still have the original earbuds, but they've long since died.
 
I had some cheapie iRock beige thing with only 32 megs of storage. Replaced it with a minidisc player, which I actually loved. The software used to connect to it didn't work after I migrated to a new OS, so I got an iPod 5.5. Stayed with apple since.
 
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Before this is was my beloved CD player, I even bought all my jeans making sure the CD player fit, then along came the iPod and I never had that problem anymore.
 
A pentium computer?

A Palm Pilot. I remember the memory was crap, but I loaded a few movie quotes into it for randomness.

I even continued to use the Palm Pilot after the iPod because the iPod would skip during runs sometimes.
 
An Ericsson HPM-10 on an Ericsson R520m, it came with a parallel port MMC reader, which wasn't a lot of good with my G3 iMac. The minidisk player I had before it was much better.
 
It was some el cheapo one I can't remember the name of. I went through several of those before getting an iPod Nano 8GB for Christmas 2007. Now I have a 4th gen iPod Touch running iOS 6 and I've never looked back since.
 
My first MP3 player was the original "stick of gum" iPod Shuffle that I bought in spring of 2005. It held a work day's worth of music and was a great first player. It was during this time that I "digitized" over 400 CDs into iTunes so I could pick and choose which songs I wanted on my iPod.

Finally upgraded to a iPod Nana 3G (the fattie form factor) and that is STILL my go to iPod (iPhone is limited since it has "other stuff" chewing up the memory). The shuffle sits unused in a drawer....

The best iPod Nano was the 5G...recorded/played video, had a beautiful form factor, and the original clickwheel (which you can operate in the dark or in a pocket). Starting with the Nano 6G...it was downhill for the Nano line.

Biggest iPod gripe has been the capacities have not grown on the shuffle and Nano.
 
Clickwheel iPod from around 2004 was my first MP3 player

Stole the pic from Wikipedia :p
 

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Last month was my 10-year iPod anniversary.

First MP3 player (and iPod) was a 10GB 3rd Gen, bought in June 2003 for $300.
 
First: Sony MiniDisc player

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Second: Rio 500 - 64MB internal, and I had a few 32MB and 64MB SmartMedia Cards. Good times.

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Third: TDK Mojo, because it was the cheapest MP3 CD player with a screen to display artist and song info, and folder browsing.

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My first MP3 player was a Rio 500. It came with 64MB and was upgradeable to 128MB.

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It was really not good. It was slow to load via USB 1.1 and only held an hour of music. It was nearly useless.

I got my first iPod a few years later. It was a 3rd gen classic that I still use here and there to this day.

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It still rules. :)

Best iPod ever made!
 
I don't have any pictures but my first mp3 player was a piece of crap that had 64meg and I would put as many 128k mp3s on it as I could. So glad I switched to an iPod a few months later and I never looked back. I have my iPhone 5 for avg use and when I need to really get my music going I have my 4th Gen 20gig iPod. Replaced the battery in it last year so she's ready to go about 6 more years.
 
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