Why can't I get a lot of my downloads on my playlist in iTunes to play on my iPod?

[iMore Question]

I can't get a lot of my downloads on my playlist in Itunes to play on my ipod.

A lot of my downloads under playlist on my itunes look faded on my ipod & will not play on my ipod. They play on the computer itunes just fine, but not on my ipod. How do I load them so they will play on my ipod?

 

[Bigeric23]

Re: I can't get a lot of my downloads on my playlist in Itunes to play on my ipod.

Have you tried clearing your iPod and then syncing it again?