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Once you connect your friends drive you should be able to play any file on it with VLC media player. Some older laptops have an S-video output on the back that'll go straight to an RF modulator (you'll need to grab audio from the headphone jack too), if not HDMI and Display Port are based on the DVI standard and there are simple dumb cables that can convert any of those to HDMI (DVI usually lacks digital audio so you'll have to grab from the headphone output, but most laptops I've seen feed digital audio over HDMI and Display Port). If all you have for a second monitor output is VGA they make VGA to composite adapters too. You'll probably need to right click on your PC desktop and go into adjust screen resolution and detect monitors and play with a few settings to make it work (some laptops have Fn buttons for rapidly connecting a external monitor for presentations).
Once you have composite video a good RF modulator and your where you want to be.
I basically do this for much of the stuff I watch.
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