For me, it would have to be this: F/A-18 Interceptor for the Commodore Amiga. A demo of it playing at a computer store is what inspired me to buy my first computer and subsequently frustrate my family by taking over the TV until I got gifted a VGA monitor to get me out of the lounge room I've yet to come across an equivalent flight sim type game to be as fun to play as that was.
On the tech side, OS2 and DesqView also bring back fond memories of being able to use my 386 IBM clone computer while my BBS continued accepting calls from users.
Ah the good old days :)
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