Hello Henry,
Jul 23, 2017 Syncing video to iPhone 3G or earlier, iPod touch (1st or 2nd generation), iPod classic, iPod 5th generation, or iPod nano (3rd, 4th, or 5th generation) Make sure you have the latest version of iTunes installed on your computer.
Thank you for the details of the issue you are experiencing when trying to sync your movies purchased through the iTunes Store to your iPod classic. I found an article with some useful information:
How To Download Videos To Ipod Classic
The iPad and iPhone 4 can play High Definition (HD) content and Standard Definition (SD) content. iPods and the original iPhone, iPhone 3G, and iPhone 3GS can play Standard Definition (SD) content. To find what video formats are supported, see the Tech Specs page, click your device's product family, and then your specific model. All HD purchases from the iTunes Store also include an iPod/iPhone-compatible Standard Definition version to accompany the HD version. When syncing an HD purchase from the iTunes Store, iTunes will automatically sync the SD video for devices that require SD content.
You can find the full article here:
Software For Ipod Classic
You can download the SD version of the movies from your list of past purchases. You can find the steps to do this in the section titled 'Apps, Books, Music, Movies, or TV shows on a computer' in the following article:
Thank you for using Apple Support Communities.
Best,
Sheila M.
Aug 16, 2013 6:36 AM
Apple's iPod is one of the most popular MP3 players available, with the iPod Classic being one of the most popular models. This model has one of the largest storage capacities out of all the portable audio players in the iPod family: with 160 gigabytes of storage, it can hold up to 40,000 songs. Start enjoying and transferring music to your iPod Classic today.
Step 1
Step 2
Open up iTunes from the Start menu or via the iTunes desktop icon.
Step 3
Connect your iPod classic to your computer's USB port using the iPod's USB sync cable. Wait for iTunes to recognize your iPod and display your iPod's current files and music lists. You should see the name of your iPod (e.g., Steve's iPod) under 'Devices' in the left-hand menu. Click to select your iPod device.
Step 4
Go to 'File' and select 'New Playlist' to create a new music list. Or click a music list that is already displayed under your iPod's name that you want to add a new music file to.
Click 'File' again and select 'Add File to Library.' In the 'File to Library' window, select the arrow button next to the 'Look In' field to find where your music file is stored. Once you find the correct file, click the 'Open' button. iTunes will then transfer your selection to your iPod Classic.
Tip
- Click 'iTunes Store' in the left side of your iTunes window to purchase music to transfer to your iPod classic.