1st generation ipod won't download music

Question

My firend just bought a 1st generation ipod and was only able to download a couple songs. He asked me if I could try and download some of my music on it cause I have a 20GB ipod of my own that works perfectly fine. But when I plug it in it just sits there and wont respond while I watch the little spinning circle so then I cant use my mouse. I already had to shutdown my computer to get my itunes to start working again. I dont know what to do with it...help!

Answer 1

This is the 1st gen iPod shuffle, that looks like a white USB flash drive, with a built-in USB plug?  FYI - This document shows the four shuffle models
http://support.apple.com/kb/HT1719
If it's a 1st (or 2nd) gen shuffle, select it in iTunes.  Toward the top of the iTunes window, there are two buttons that say Settings AND On This iPod.  The Settings screen is probably what you already used, "to set certain options."  Click on On This iPod.  This screen shows a list of songs that are currently on the shuffle, and you can use this screen to remove songs from the shuffle (and change song order), once you have songs on it.
At the bottom of this screen, there are Autofill controls.  That is one way to load the shuffle.  You can "automatically fill" the shuffle from your iTunes music library, or from a playlist.
To add individual songs, drag songs from your iTunes library and drop them on the shuffle.  The easiest way to do this is to use the iTunes sidebar (along left side of iTunes window).  If the sidebar is hidden, from the iTunes menu bar, under View, select Show Sidebar.  Find the shuffle in the sidebar, under the heading DEVICES.  From your iTunes library, drag songs (or other audio items) and drop them on the shuffle.