Microsoft Flight Simulator 98

The 1997 entry, and the one that widened what you could fly. Cessna 182 Skylane, Bell 206 JetRanger, a Schweizer 2-32 glider and a Sopwith Camel, plus fly-anywhere terrain and a fresh New York scenery. A helicopter and a glider in the same box changed how the sim was used, because neither of them flies like an aeroplane.