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I'm not sure if this is correct, but I remember someone saying it only works with iPod Classic and iPhone and iPod Nano (The new style ones)
Try the Xbox website FAQ, or google to see if anyone else had similar problems.
hm, i actually had no idea you could do this. I just tried it with my ipod and it worked fine. I plugged it into the front of the console. I have one of the new 360's with the HDMI port BTW. I just plugged it in and went to media and then music and it came right up. Also I have a 30gb video ipod, I think its a 3rd generation.
I found this on Xbox.com though...
http://www.xbox.com/en-US/support/systemuse/xbox360/digitalmedia/ipod.htm
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