1990 - Dynamix
One of the great classic flight sims, Red Baron was a huge hit, still appearing in stores 7 years after its release. Though the flight model was simplified and did not aim to be a true simulator, many of the 20+ WWI planes one could fly had unique physics to simulate real world quirks.
Nov. 1997 - Dynamix / Sierra
The sequel to Red Baron was a year late and rushed to market in time for christmas, resulting in a very buggy release with many planned features left out. The flight model was broken, enabling WWI planes to climb like WWII fighters. Online multiplayer was present, but so flawed that few found success to get it to work. It's no wonder Sierra rushed Red Baron 3D a year later, with all issues resolved, flight model corrected, and people who bought RBII to get a free upgrade.
Oct. 1998 - Dynamix / Sierra
Red Baron 3D is a heavily patched version of Red Baron II. It gave better graphics and vastly improved the flight model, and added support for 3Dfx video cards. It's also seen as the first online simulator capable of team play, with dozens of online virtual squadrons being formed, along with an active community of modders. Its automatic mission generator was also brilliant and unique among other flight sims.
Oct. 1999 - Dynamix / Sierra
Dynamix, in an attempt to appeal more to the masses, decided to make an arcade WWI flying game as a spin-off from its Red Baron series. The results were disastrous. Critics left scathing reviews of the game, saying graphics were ugly and very 2D, flight model was shoddy, gameplay was boring, and worst of all, zero joystick support.