Man, do I feel guilty about this-- Microsoft Crimson Skies.
Yes, it is a product of the evil empire, but I purchased it at a deep discount.
Along with a great shoot-em-up game with an aerial theme, you get a half-hour radio play that is not half bad. The flight simulation is apalling, but accurate flight characteristics would take away much of the fun.
I bought it, because it was based on a boardgame that I own, but could never find anyone else to play with(my wife prefers simpler games like the crayon rail games, or more involved games like AH Advanced Civilization [not to be confused with the computer game of the same name]).
Aside from it supporting Microsoft (which has nothing to do with its play value), it was my favorite game purchase, after Master of Orion.
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