Well I´ve only done it with games that are for virtual console but I don´t think that´s what you meant.... with Movies that would be a different story (I own 4 Back to the Future boxsets)
The one game I've done it with is Elder Scrolls IV Oblivion. It was the first game I bought for my 360 and I played the hell out of it then. Years later I got it on sale for the PC which is now my platform of choice mainly for the mods and Shivering Isles.
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