Put video on PSP

Get with the right program
If you're going by the book, the "official" way to get videos onto a Memory Stick Duo (and by extension, your Sony PSP) is to go to Sony's Web site and purchase Image Converter 2.0 for $20.

Originally designed for use with Sony's CLIE handhelds and Handycam camcorders, Image Converter 2.0 performs the basic function of converting movies into the proprietary MP4 format used by Sony's gaming system. But because it wasn't designed for use with the PSP, Image Converter 2.0 won't detect your hardware when you've plugged it in via USB, and it won't know to create the right folders on your Memory Stick Duo so that the PSP will recognize your media. It also doesn't support conversion into wide-screen formats, thus wasting what may be the PSP's most compelling feature as a video playback device. Finally, it'll set you back $20, when there are better options (we'll show you the best one) available on the Web for free. In the final analysis, this is a case where it doesn't pay to follow the company line.
In the wake of Image Converter 2.0's inadequacy, it didn't take long for a slate of freeware PSP video programs to crop up for download. In terms of video quality, customizability, and overall ease of use, the best of the breed is Videora Labs' PSP Video 9.0, available for download here.

Watch the video to see this software in action.
PSP Video 9.0 supports a wide variety of source formats, including MPEG, AVI, MOV, and WMV (if your source video is coming from the Internet or a digital video recorder) as well as VOB (if your source video has been ripped from a DVD). We leave it up to you to ensure that your source videos are attained through legal means.

Unfortunately, PSP Video 9.0 is currently a Windows-only program; if you're a Mac user, you'll want to check out PSPWare ($15) or iPSP ($20, and also available for Windows). Both programs offer conversion and syncing features similar to those of PSP Video 9.0. If you want to preview your converted videos before transferring them to your PSP, you'll also need the latest version of Apple's QuickTime player, available on Apple's Web site. Once you have all the necessary software installed, connect your PSP to your computer via USB, wait until your computer detects the new device, then start up PSP Video 9.0, which should detect your handheld automatically. You're ready to convert your first video!