Currently Being ModeratedNov 20, 2012 2:19 PM (in response to bruce hyman)
Is the manually manage music and videos option enabled from under the iPod's Summary tab in iTunes? If so, you must manually delete music from the iPod via the iTunes interface.
You can do this by plugging your iPod in and clicking the small black triangle next to your iPod from under the Devices section in the left hand pane of iTunes. This will open up a submenu of content that is indented underneath the name of your device, so go ahead and click on Music (or whatever content you are wanting to remove). Locate the track or tracks/content you wish to delete. Highlight them and hit the Delete key or choose Edit -> Delete.