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3rd gen 20gb i love that thing and we have been through so much! i have a 3g nano and now i use a 4g nano as my primary player nowadays
 
I don't even think I saw an ipod until the 3G iteration.

No kidding. I guess had too many broke friends who couldn't afford such things. :)

My first was the 5th gen 30GB video model in black. I bought it from the Apple refurb store right after the 5.5 update. I still use it as my primary iPod. I replaced the battery in in a couple of months ago, which was fairly painless.

A couple of months ago, I picked up a 1st gen 16GB Touch. Best Buy had them discounted to help clear out inventory. I thought the price difference was enough to warrant getting the first gen instead of springing extra for the new model. I still love it, although the external volume controls would be nice. I have started using the Touch as a PDA of sorts.
 
30GB 4th gen that I found in the snow one morning while walking to work. It looked like it had been there over the weekend and I was pretty surprised when after thawing out, it worked fine. I felt like trying to find out who owned it, but then I noticed it was filled with Snoop Dog and Bone Thugs n Harmony. I felt like I was doing a service by restoring it to factory defaults. :p

I've since then bought an 80GB Classic, 2GB Shuffle, and 16GB iPhone.
 
iPod 5G black with 30Gig. Bought it used because I couldn't get the money for a new one. But I'm still using it.
 
My first iPod was the 20GB U2 edition, not because I liked the band, but because of the colors. Call me crazy for spending the extra money just for the colors. ;)
 
I bought my first ipod which was a 2nd Gen 20GB the same day I bought my first Mac which was a Dual 1Ghz Power Mac. I sold the computer a few years ago, but still have the ipod packed away somewhere. Have gone through about 6 different ipods and now have a black 8GB Nano and 1st Gen 16GB iPod Touch.
 
I was a late adopter. Got my 5G 60 GB video iPod to go along with my MacBook in August of 2006. Both of those were my first Mac purchases; my wife had a 1g shuffle before I got the 5g, though.

Now I have a 16 gig 1G touch, and my 5G has slowly been phased out...
 
gosh that thing is hideous!! i still really like that one that had the 4 touch sensitive buttons on it that lite up - generation 2 was it? I never owned one but I always thought it was pretty darn cool.

That would be the 3rd gen - the 20GB model was my first iPod. 1st and 2nd gen look almost identical.
 
By the way, I nearly bought a 5.5G iPod 30 GB (white case) when I bought my 2G iPod nano (4 GB blue case). If I did that it's likely it still would be my only iPod I have now.
 
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