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Yes I know this is a DOS game, but it’s also kinda a windows game? Back in the day my copy of DOOM II ran using DOOM 95, a windows-based launcher. My first encounter was on a windows 95 game demo disc that came with our brand new Pentium 133 in 1996. DOOM 95 allowed use of higher resolutions and also level selecting without inputting any codes.
Anyway, the main reason I suggest DOOM is because I understand it was ‘ported’ to Windows to help promote Direct X, and help move games onto the platform, which I think is a kind of interesting point a podcast could look into. We could also look at Doom 3 at the same time.
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