First, you need convert all kinds of DVD or video to "special MP4" for iPod. IPod supports these formats: iPod MOV MPEG4, iPod MPEG4 and iPod AVC H.264.
Download an iPod video converter, I recommend Aimersoft DVD Ripper (You can also choose other "DVD Ripper" of course). Free download it here: http://www.aimersoft.com/dvd-ripper.html#161
How to convert video to MP4 for iPod?
1. Download the video converter software and install it.
2. Run the software, click "file" or "add video" at the top left corner to load video.
3. Click the "Profile" drop down list to select an output format you want. There is a lot of format to be selected, and select iPod--iPod Video MPEG-4(*.mp4) or iPod--iPod Video H.264 (*.mp4) for your iPod.
4. Set the output path with the "Browse…" button.
5. Press "Start" button to start the conversion.
Tips: While convert DVD to MP4 for iPod, you can learn the guide by clicking:
How to convert DVD to iPod Video MP4?
How to put the MP4 on iPod?
1. Connect your iPod to your PC.
2. Click "video" on iTunes.
3. Drag the MP4 file you converted to the iTunes video list.
4. Wait for a few seconds (The length of time is depends on the size of your video).
Tips:
1. If there is no change with your iTunes, drag it to the list again.
2. After those step, let your iPod go, then you can find the mp4 file you converted in "video" option.
How to set playlist on iPod?
1. Connect iPod to Computer.
2. Click "XXX`s Library" in iTunes, then choose "Add New Playlist" .
3. You can type in a name for your playlist as movie, TV, MV etc.
4. Drag your video to the right playlist.
Hope this may help you. Good Luck!