Q: What's up with "...waiting" for a download on iTunes?

Hey there Tom Perkins1,

It sounds like you have 3 downloads that seem to never get out of the Waiting stage. I would recommend starting by deleting the songs from your iTunes library, even if they are grayed out:

How to delete content you've downloaded from the iTunes Store, App Store, iBooks Store, or Mac App Store

http://support.apple.com/kb/HT5772

Mac or PC

1. Open iTunes.
2. From the Library pop-up menu, choose Music.
3. Click Songs in the navigation bar.
4. Click the song you want to delete.
5. Press Delete on your keyboard.

In iTunes 11 or later, the album cover art will remain visible, but a Download icon will appear on it to allow you to download the item again (in countries that support this).

Note: If you didn't purchase a song from the iTunes Store, you can't download it again for free from iTunes in the Cloud. You might want to back it up somewhere on your computer.

Then go back to your purchased history in the iTunes Store and download them again:

Download past purchases

http://support.apple.com/kb/HT2519

Thank you for using Apple Support Communities.

Regards,

Sterling