For Microsoft, a generally good answer is probably the first Halo. It's genre-defining for sure, and definitely gave the Xbox a reason to exist.
But there is one game out there that could probably slay it as the greatest title Microsoft ever created.
And that's Microsoft Flight Simulator. Older than even Windows, and had no other competition to rival it. It was always a niche product, sure, but it had a charisma in the market very few cult titles have, even today. It also gave rise to the excellent Combat Flight Simulator spinoff. And lastly, I've never seen a genre stall so hard like the flight sim genre has since Microsoft pretty much left it for dead around 7 years ago.
During 2004-2007, while I probably spent 50,000 words arguing with people about the fucking lore of Halo or whatever, my friend spent most of those hours playing Flight Sim 2004/X. He's now a professional pilot, travelling the world and earning ridiculous money.
So here's to you, Microsoft Flight Simulator. May you be an eternal reminder that Microsoft can create fabulous things that aren't tied to Microsoft Office when the folks at Redmond actually put their minds to it.
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