Why does screen freezes when I attempt to play certain songs in my library

Why does my screen Freeze when I attempt to play certain songs I have downloaded from CDs into my library?
I have just received my Nano and I'm unsure if I want this to keep happening

Apple removed my previous post because I referenced jailbreaking which is a violation of the TOS.  Sorry about that! 
That said, I can't think of any way to get around the file size limitation.  I suppose itunes match isn't really meant to give you access to play all your songs anywhere.  It instead gives you the opportunity to download your songs via wifi when you aren't at home.  I can't see that it makes any difference one way or the other to Apple but it obvioiusly would make a difference to the wireless provider. 
So now, my question is whether this happens on with all carriers.  I have experienced this on AT&T.  Does anyone here have Verizon or Sprint?

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