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Well, just between the Ipod and Zune I would have to say Zune. I shelled out $250 for my wife's Zune a little over a year ago, and neither of us were big fans of Microsoft but after she got it she fell in love with it's interface. It's a 30GB 1st Gen version but still nice. No dead pixels or problems, plus you CAN add songs using windows explorer. All it requires is a simple registry fix.

Personally I have a 4GB Sony Walkman. It is slightly behind interface-wise compared to Ipod or Zune but when it comes to sheer audio clarity and performance, it blows both of them out of the water.