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I have lots of playlists on my iTunes library, and I want to be able to copy the music of certain playlists to a flash drive to play on a stereo system. I have too many songs in too many folders to just copy the raw .mp3 files, so that option is out. Any other ideas?

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Unless I miss something, you can just drag & drop the playlist to your USB drive.

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I don't know why, but I couldn't the first time. I decided to try again, and it just started copying :S I have no idea what changed – Luke Jul 28 '11 at 2:42
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iTunesExport is a Java program that you can use to export iTunes playlists including the music files to a specific directory or drive.

If you regularly want to export iTunes playlists the iTunesExport command line version makes it easy to create bash scripts you can reuse.

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