FAT32 has a 4GB file size limit. Ordinarily this would be a bad thing, but since the XBOX 360 won't play any video files larger than 4GB (except WMV, naturally), it's not a problem at all.
As long as the File Size is under 4GB, the XBOX will play it, provided it was ripped to H.264 specs. If it's not playing a file, check its file size and its video stream info on your Mac using Quicktime. You may need to re-encode the files.
Also note: Mac OS 10.6 Snow Leopard uses a different system of calculating "gigabytes" from the rest of the world. An Apple gigabyte is a little smaller than regular gigabyte.
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