Take a look at MCE Tunes. Could this be the answer I was looking for?

According to Chris Lanier, the new version (coming very soon) will let me watch iTunes Video (purchased, and I’d have to assume downloaded) on my Xbox as Media Center Extender.

I never purchase software for what it will do “soon.” As a result, I’ll wait until the next release is out but, … this could get very interesting.

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