John R (SA) replied:

All I can suggest is, in iTunes;

View -> Show Duplicates (near bottow of drop down menu)

Then go through and select all the ones you want to delete.

If you hold down the Control key while single clicking on a song, it will select only the song you click on. This way, you can go through and select all the ones you want to get rid of at once, then hit delete at the end.

I am not aware of a faster way, though wish I was!!!

RustyHelen replied:

That's it as far as I know but you might try the Ipod discussion group. Just Google Ipod and I reckon you will find it after a bit.
Rusty