Sorry I'm not a Mac user (our Mac users aren't around ATM)

What format are the songs?

Can you launch the songs from LW & do they play ok? If you manually transfer the files to iTunes, do they transfer without a problem?

If the songs seem ok & you can manually move them to iTunes, try LOTR's advice in the threads below

http://www.gnutellaforums.com/genera...re-itunes.html

http://www.gnutellaforums.com/genera...gs-itunes.html

If nothing there helps, try deleting LW's preferences folder. This thread has info: http://www.gnutellaforums.com/295239-post5.html