Itunes doesn't allow me to send some songs to my iphone or allow me to play them?

When i drag and drop some music files on my itunes it doesn't allow me to play or send the song to my iphone? The song details are shown in a light grey with the 'refresh' like button the very left hand side.

I had a problem getting any calendar events after a hd failure and reinstall. Someone here told me to try this and it worked!
1. Launch iTunes - Preferences - Devices - Reset Sync History - Confirm - Give it 1 min. You may or may not see a progress bar. Ensure Outlook is closed when you do this.
*Now go ahead and sync Outlook Calenders to iPod
2. Attempt to try and sync using the different USB Ports in the system and see weather or not syncing takes a bit longer and actually copies information over
3. If you are able to Restore the iPod as a new iPod so it has a fresh info.. And sync everything to it like it is the first time.
Hope it helps!

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