Hardwar (PC, 1998)
This was really more of a flight simulator than a game, but we guess throwing in some open-world missions can qualify Hardwar as such. You play as a pilot of an aircraft called "Moth" in a city called "Misplaced Optimism," which sounds more like the name of a band than it does a metropolis. Anyway, the game tasks you with earning money as a pilot in the city, either by staying on the straight and narrow and becoming an honest trader or by fitting into the shady crowd and pirating cargo for yourself. One of life's many choices.