At the risk of giving bad information, I believe the random means that the files that have been loaded into the gramophone folder at the start of the game, will play in a random order. For the Churchill speaches, I think all you would have to do is copy the speach to the gramophone folder inside the date folder already in commander. I do not think any sub folders inside the gramophone folders would work properly.
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"Some ships are designed to sink...others require our assistance." Nathan Zelk
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