Things You'll Need
Instructions
Hook your PSP up to your computer using the Mini-B USB cable and set the PSP into USB Mode by navigating to Settings and choosing "USB Settings" on the XMB home menu.
Open your iTunes directory, the folder where your iTunes library is stored, and locate the files you want to transfer to your PSP. Access your PSP memory stick directory by double-clicking its corresponding icon in My Computer. Mac users will find the icon on the Desktop.
Find the "MOVIE" folder in the PSP memory stick directory. Drag the video files from your iTunes directory and drop them into the "MOVIE" folder. When the transfer is complete, safely remove the USB cable from both devices. Navigate the XMB home menu to the Movie menu and open the memory stick to find the movies you transferred.