Purchased Music Is Not Authorized On PC

Greetings! Some of the music I purchase through iTunes(about 15%) won't play on iTunes on my PC(Windows). Those songs play without issue on my iPad and iPhone, but it says I need to authorize my computer to play them on my laptop, and asks for my Apple ID and password. After I enter the password for my Apple ID, it tells me that I have authorized my computer(even though I did that long ago), but won't play the song. When I click it to play, it prompts the 'please authorize this computer' message again, and again, and again. I have the latest version of iTunes on my laptop. Any suggestions would be appreciated. Thanks!