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Unfortunately, that's not the best way to copy media over to your device and play it. If you can, use the Sync feature in Windows Media Player to copy your media over. This should automatically add the media into the library of your device. If you choose to transfer your media manually, then you can still manually add your media into the library by selecting Menu > Update Library. Windows Media Player Mobile will sniff out all tracks and videos you have on your device. Following that, select "My Music", and then pick the media you want to play. This will add it into a temporary "Now Playing" list. Each track in the list should then play after the other.
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