Download and install a DVD ripping software. A popular ripping solution is DVD Decrypter. This software will transfer all the information stored on a DVD onto your computer's hard drive. Make sure you have an adequate amount of space on your hard drive (large movies can take up to 4-8 GBs of space).
Rip your DVD. Place your DVD into the DVD drive, and follow your software's instructions for ripping DVDs. This process can take a couple hours depending on your computer's speed.
Connect your PSP to your computer. Once your DVD is finished ripping, connect your PSPs USB cable to your computer.
Download and install PSP Video 9. This free software will convert your ripped DVD files for use on the PSP.
Convert video using PSP Video 9. Select your ripped DVD's VOB file. You may also specify the location of your PSP. Click the "Convert New Video" button, and wait for the process to complete.
Copy your video to your PSP. This can be done with PSP Video 9. Click the "Copy" button, and your video file will be copied over to your PSP. You may want to check the video for quality before completing this step. You can now view your DVD footage on the PSP.