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Thanks to smart playlists in iTunes, you can build a playlist gathering the best songs of your library in few seconds. I recently had to copy a such best of selection to an external hard drive. A simple drag & drop from iTunes to the Finder can do the trick, yet resulting in a mess of unrelated files now all located in the same directory.
So, what is the easiest way to copy a playlist content to a specified location and have the folders arrangement of your source files duplicated on your destination drive ?

Here is the solution that I’ve reached, unfortunately it involves no less than 3 different steps.

Export the playlist to M3U file

Because it can’t be done directly in iTunes, you have to export your playlist first.
Select your playlist and right click Export then choose the M3U8 format. M3U export has been added recently to iTunes (in one of the 9.x release), so upgrade your iTunes if the only choices you’re faced with are text and xml.

Fix the M3U file

iTunes saves M3U files using DOS/Windows newlines, fire up your Terminal.app to correct that :

tr '\r' '\n' < input_m3u

Transfer files using cpio command

cpio is the perfect tool to copy files listed in the M3U. Run it with -dp options to activate pass-through mode and automatic directories creation :

tr '\r' '\n' < input_m3u | cpio -pd  destination_directory > m3u_file

VoilĂ  ! All files are copied to destination and the directories structure is preserved which is neat when you sort your files by artists or year, etc.