Your video bitrate and video resolution are too high. The iPod classic supports a maximum resolution of 640X480 and a maximum mpeg-4 AVC bitrate of 1500kbps. That's all for baseline profile mpeg-4 AVC. It supports up to 640X480 and a bitrate of 2500kbps with baseline profile 3.0 mpeg-4 AVC. As I said, it all depends on the baseline profile you are using when encoding the videos. Not only that but the file types (*.mp4, *.mov, and *.m4v) all must fit within a certain specification for iPod classic compatibility. Hence, if DVD Fab offers an iPod classic profile for encoding, you should stick with that. If not, you should use DVD Fab to rip the DVDs then handbrake (a free program) to encode the ripped DVDs as it offers an iPod classic profile.