At my home I have a wireless network set up for my family's laptops, all currently running Windows Vista. Because of where my router is in relation to my Xbox, it wasn't realistic to connect my Xbox to my computer via Ethernet cable. So I went out and purchased a wireless adapter.
Since all my computers are connected to over the network, my Xbox automatically detected my computer. In my experience, the whole process has been seemless. I keep all my media (music and videos) on my computer, and use my Xbox as a set top box to watch the TV shows and movies I've ripped to my hard drive.
When in game I can bring up the dashboard, go to the music section, select the artist or song I want, and play it while I'm playing my game of choice. This is a slightly expensive option, but is very easy in practice.P.S. If you are using iTunes as your media player on your computer, you have to make sure to import all the media you want into your Windows Media Player library.
All in game media players that I have come across are not capable of playing music off the network, they require it to be stored locally on the xbox or attached locally (external USB drive). The external USB drive is acutally how I circumvent this very issue, I've got all my media (videos/music) ripped to a 1TB external drive that I can just switch the USB cords from my computer to the xbox. Bummer, but I hope this helps.
I ahve done it you start the game and open your 360 menu and go to the folder with your music and hit play.
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