I recently wrote an Excel 2007 workbook that allows you to compare and modify iTunes playlists (assuming you have Excel on your computer). It was my semester project for an ISys Spreadsheet Programming class that I took. Here's the link: http://vbaprojects.blogspot.com/2010/04/itunes-playlist-comparer.html You can download the iTunesUtils.xlsm file from there. Note that you'll probably have to enable macros for it to work.