Itunes won't let me delete songs

Going through my normal routine of trying to clean up my library today....
I select the songs that are duplicates or the ones I don't want in a playlist anymore and hit delete and nothing. The option is not even highlighted in the menu.
Anyone else have this issue? It's not a keyboard delete key problem either.

It sounds as though you are need to manage your music manually. You can't delete from the iPod if your are on auto sync.
See this tutorial
http://docs.info.apple.com/article.html?artnum=304708

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