You can't. The DRM that comes with iTunes songs prevents you from playing them on your 360. The only way to get around this is to burn the songs to a CD and upload them to your 360 from there.
You must connect the ipod with the songs on it to the xbox via USB connection.
coolkid5554444
I'm pretty sure that he's asking how to play songs from iTunes once he's connected, not how to get his iPod hooked up. Just thought I'd clarify to avoid any confusion.
The problem lies in the fact that Steve Jobs is nowhere as cool as Bill Gates. Fact.Tcox22
Steve Jobs doesn't want DRM. If Bill Gates (Microsoft) would back him up they might actually be able to do something about it. Bio_sm0g, buy your digital music from Amazon MP3. It's higher bitrate, cheaper, DRM free and will play on your 360. Also, there are programs out there you can buy that re-record your DRM protected music into a DRM free form. If you have a lot of music from the iTunes store it may be worthwhile to check them out. [Hopefully it's okay to mention this here.] I bought one and converted all my iTunes store purchases to DRM free mp3. I don't buy music from iTunes anymore, Amazon all the way.
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