iPod video (5 gen; 30 gb) in the Summer of 2006. I sold it (and regretted it) and got a new iPod classic 120 gb in 2009. With the exception of the iPod touches (which isn't really an iPod IMO), these and the early gen. nanos were the best ones ever made.
iPod Touch 2G 8GB in october 2008. Then my 4th gen in September 2010. Those are my only two Apple devices...
iPod Video 80GB with about 2500 songs, I threw it away after I dropped it and the front black part came off from the stainless part :/
Black 30GB 5G iPod Video... I went through about three of them because the hard drives gave out in all of them. Second was a 2G iPod Nano (think it was a mere 4GB). After that I dove into the first gen iPod touch and it amazed me... That is until the 2G came out like two weeks after I bought it. I guess I learned the hard way that it is not a good idea to buy an iPod touch in August.