You need to make sure the music your putting onto the PSP is in MP3 format. Other then that here is the steps to make sure your uploading the music properly:
To get everything working, plug the Sony PSP into the Windows PC via
USB cable, plug the PSP into the wall, then turn both units on. On the
PSP, click the "USB Connection" button (on the Settings menu) and,
hopefully, your PC will beep and tell you that it's found a new
"removable disk": your PSP.
Using Windows Explorer, find the new PSP device and if there isn't
already a folder named MUSIC then create it and drop in MP3
format music files
Then at this point you should be able to access the music on your psp.
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Best thing to do is Format the Memory Stick from the System Settings menu. Then the folders will be in their perfect locations for the PSP to read your media. You just drag over the media into the respective folders, mp3 goes into MUSIC folder which is now inside the PSP folder. So its like this: root-psp-music-*.mp3.. Follow bens process above to get the music from pc to psp..
rock out with the psp out. ONE!
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