Downloads

Repeated requests to authorize an already authorized computer for recent store downloads typically indicates you have corrupt or incomplete copies. Delete the tracks that won't play from your library without hiding from your purchase history. Redownload using the cloud links that should remain, or close iTunes and reopen if they don't show up straight away. While downloading click the activity widget and turn off the option that allows for simultaneous downloads.

If that hasn't helped see If iTunes prompts you to authorize your computer when you try to play iTunes Store purchases - Apple Support as above.

tt2

Hi TheeKnightOfTrashe,

Welcome to Apple Support Communities. I understand that you recently downloaded an album to iTunes on your PC, but three of the tracks are prompting for authorization. I know it's important to be able to listen to all of your purchased content; I'd like to help. I'd recommend following each set of steps in the following resource and trying to play the affected songs after each: If iTunes prompts you to authorize your computer when you try to play iTunes Store purchases

Let me know what you find after trying these steps.

Best Regards.