Why are all of my purchases downloaded from the cloud but can't be played from iTunes?

I recently updated iTunes as prompted. Many of my songs disappeared. I was able to get most of them back. Some of the songs I purchased will not play in iTunes. I've checked my history, and it says that all songs were donwloaded. Why won't they play?

But I would think that the purchases would be saved onto my Itunes account and therefore redownload into my computer. I have been able to retrieve about 9 of the 20+ songs that I bought by syncing my phone however the other purchases are still not there. Also, when I go to the Itunes store and back to the purchases, the button you press to buy it says "PURCHASED" so I know I don't have to rebuy them. How do I redownload the music I purchased previously?

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Why are all of my purchases downloaded from the cloud but can't be played from iTunes?

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