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this can happen if you have moved things around on your hard drive because itunes will not know where to look for the song anymore, have you recently reorganized your music or changed the names of the folders they were in. Also does the song have a little triangle exclamation point thing next to in in iTunes?
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My posts looked so naked without this down here so I figured I would put something down here just so my posts didn't feel like that dream where you are the only one naked in a room full of clothed people.
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