Songs are greyed out on iphone and itunes unable to play music

I have loaded all my songs on to imatch.
Now I am unable to play over half my itunes songs.
On my iphone they are greyed out and don't have a cloud next to them
On itunes the songs have a cloud next to them but i can't download the songs nothing happens when i pressed the button.
Please some one help
Mac Version 10.8.4
Itunes Version 11.0.4
Thank you

jhl1951,
Is the Shuffle still configured to manually sync content to it? You can check by making sure the proper configuration is made from under the Shuffle's Summary tab in iTunes while it's connected.
B-rock

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Some of my iTunes match songs are greyed out on my iPhone

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Songs are greyed out on iphone and itunes unable to play music

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