Previous purchases not downloading to IPhone4

Hi!
My friend is having some trouble downloading his previous purchased songs onto his Iphone 4. He goes into the itunes store app, to download his previous purchases. When he clicks on the little arrow to start sycing it to his iphone, it says its downloading, and then it stops and the little arrow shows again. Can someone please help. Thanks!

Just keep on buying episode by episode - previously purchased episoded aren't applied to to a multi-pass in order to reduce its price.

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