If your generation of Ipod is 2 or lower, it'll work on Windows 2K, his 3rd generations needs XP or higher. However, there's a workaround
1. Download the most recent Winamp Media player from winamp.com
2. Download iPod
Support_v302.exe from
http://mlipod.sourceforge.net/
3.Install Winamp, then the plugin.
4.Choose correct Ipod when prompted.
5. Let it copy your music folder.
6.Connect your Ipod and let it sync with the player, or press sync.
7. You will see your Ipod under Devices on the left side.
8. For videos, you can download the Xilisoft Ipod Converter 3 from download.com to convert regular videos to Ipod format.
Hope that helps