Q: I have transferred my music to an external hard drive and I cannot get it to play.  How do I have the music play?

Hi  ckholbert,

Thank you for using Apple Support Communities. Based on what you stated, it seems like you want to sync music from iTunes to the device. I would recommend you read these articles, they may be able to help troubleshoot the issue. 

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

Move content from iTunes on your computer to your iPhone, iPad, or iPod touch - Apple Support

Cheers