And it's funny that you mentioned getting into the 21st century. I've got a Windows Mobile 2003 smartphone on Verizon Wireless! The iPod just never appealed to me, but that's probably because I'm not that much of a music lover. There were mp3 players before the iPod came along, and there have been cheaper ones since. 'Podcasting' has been along long before the iPod, with a different name.
I was just surprised to find that President Bush indeed has an iPod. I didn't believe you until I did some searching, but you're right!
I was looking to buy a music player a bit before the iPod came out. All mp3 players were absolutely horrible. I settled on a minidisc player instead. Apple made the first usable consumer-electronics grade mp3 player. Before then they were unusable geek toys.
Of course, phones playing mp3s is pretty old too. I bought a Siemens that played mp3 files in early 2001.