Harry, one of our users, has created a program called PSP Shuffle. PSP Shuffle will automatically fill your PSP with photos, music and videos from the directories on your computer that you specify. After initial setup, you can literally load your PSP with media in minutes with just one mouse click.

The files PSP Shuffle chooses are completely random, and files will never be duplicated when copying to your PSP. PSP Shuffle's efficiency relies greatly on how many files you let it shuffle; the more you specify, the better it will be a filling your PSP to capacity.

Features
· Shuffle photos, music and video all at once with one mouse click.
· Percentage based system allows for more of one media type and less of another.
· Easy setup. Simply tell PSP Shuffle where to look for media and it does the rest.
· Automatically remembers shuffling preferences and media locations.
· Automatically leaves at least 2MB free on memory stick for games saves.
· Automatic discovery of connected PSP or PSP formatted memory stick.

Supported File Types
PSP Shuffle will only shuffle file types compatible with the PSP. These types are as follows:
Images - .jpg, .jpeg
Video - .mp4
Audio - .mp3, .at3, .oma, .omg, .atp

System Requirements
At bare minimum, PSP Shuffle requires the following:
· Windows 2000/XP
· .Net Framework v1.1 (download directly or through Windows Update)
· PSP and/or a PSP formatted Memory Stick

EDIT: This program is now free, get the free version in our PSP download section here.