Q: songs play in iTunes but not on iPod

Hi ibwusvnw,

Welcome to the Apple Support Communities!

From your question, I understand that some songs do not play at all on your iPod and are skipped, but they play with no issue in iTunes on your computer. There are a couple of different steps I would suggest to begin troubleshooting this situation. 

First, I would suggest transferring your purchases from your iPod to your computer. This will ensure that any purchased music content that may be on your iPod will be transferred to your computer. This will not transfer any music on your iPod that may have come from CDs or a different iTunes library, however. 

Redownload or transfer your iTunes Store purchases from an iPhone, iPad or iPod to a computer - Apple Support

To transfer purchases from your device to a computer:

1. Connect your device to the computer. Wait for its icon to appear in iTunes.
   
2. Go to File > Devices.
   If you're using iTunes for Windows and can't see the menu bar, learn how to turn on iTunes menus in Windows.
3. Choose Transfer Purchases from [device name].

​​This feature works only for content bought from the iTunes Store. Any items that you imported from audio CDs or received from other sources won't copy from your device to the iTunes library. However, all podcasts from your device's Podcasts app and copies of all PDFs and books from your device's iBooks app will transfer to the computer. Learn how to transfer media to your iTunes library.

After the transfer is complete, I would suggest syncing all of the music off of your iPod and then syncing it back on to the device fresh. 

To sync the music off of your device please follow the steps below:

    1. Select your iPod in iTunes as shown under step 3 in the next attached article. 

    2. Once the iPod is selected, select Music from the left sidebar in iTunes. 

    3. Uncheck the Sync Music box. 

    4. You will see a prompt that all music will be removed, continue. 

    5. Press the Apply button in the lower right hand corner of iTunes to initiate the sync. 

After the music has been removed and the sync is complete, sync the music back on to your iPod fresh. 

    1. Place a check in the box next to Sync Music. 

    2. Choose what music content you would like to sync. (All music, selected artists, etc.)

    3. Press the Apply button in the lower right corner of iTunes to initiate the sync. 

The attached article below also discusses syncing and is a great resource I would recommend reading over. 

Sync your iPhone, iPad, and iPod with iTunes using USB - Apple Support

Once the sync has completed and the music is back on your iPod, test the music and see if it plays as expected. 

Best regards