Well ok. Since I dont have the greatest hits CD I cant tell you with a definate yes or no. But I have VH1/Alcatraz videos on my video iPod. I had to convert them using iPod Movie Converter from
ImTOO. I recommend thier products. Now, in order for this to work we have to assume that you can successfully copy the video to your harddrive in standard video formats (.mpg, .avi, etc). If you can do that, then the program will work. The program is self explanitory and easy to use. Once you get them converted, just drag and drop the converted video files into iTunes just as you would with any old song. Bada ding!
Again, since I dont have the greatest hits I can't give anymore advice than that. I hope I didnt confuse you any further.