You can do it via the menu. I have a 2015 suburban. I connected a 1TB hard drive with about 1800 movies to usb ports on the rear of the console. Then kid 1 can use the remote to select that source and scroll through the files and choose a movie. Then then hand the remote to kid 2 who can do the same with the rear screen.
So yes, both rear screens can play different files from the same source. Hope my explanation made sense.