Uploading movies to your iPod, iPod Nano, iPod Touch or iPhone requires getting the video in a specific format on your computer first. The movie must be in your iTunes library, whether it's a movie you actually purchased from iTunes or another source, or if it's a personal home movie from iMovie or another media player.

Video Format

No matter what type of iPod you have, the movie must be in MP4 format before you can upload it to your iPod. If you are unsure as to the format of your movie, open iTunes and go to Movies. Right click on the movie you wish to upload, and select "Get Info." A window will open with information on the movie. Find "Kind" on the top of the left column, and it should say "MPEG-4 video file." If it says MP3 or any other format, you must convert it to MP4 first, or it will not play. To convert videos to MP4 format, Videora is a free, easy program. After you install Videora, go to "Convert" and select "One Click Transcode." Select "Browse" and find your video. Once it's loaded, go to Videora and select "Videos." Drag your movie into a playlist on iTunes and check "Get Info" to confirm that the movie is now in MP4 format.

Transfer Movies to Your iPod

To upload movies to your iPod, open iTunes and connect your iPod to your computer. iTunes will automatically detect your iPod, and the name of the device will appear on the right side of the iTunes window under "Devices." Click on this to open your iPod settings in iTunes. Find the "Movies" tab along the top and select it. You will see a list of all the movies in your iTunes library. Find the movie you want, and highlight it. Click "Sync," and wait for iTunes to upload the movie. Your movie will appear on your iPod under "Videos." Another option is to find the movie in iTunes and drag it to your iPod on the right side of the iTunes screen under "Devices." If you try both of these options and still do not see the movie, you may not have enough space on your iPod. Check the size of the movie by right clicking and selecting "Get Info," and check the bottom of your iTunes screen. There should be a bar measuring the capacity of your iPod that tells you how much space you have available. If the amount is smaller than the size of the movie, you may need to delete other movies, songs, photos or apps to make room.

Source:

Videora