X-Wing Alliance came out in February of 1999, and recieved great critical acclaim. The fourth game in the X-Wing series, it contained many of the same gameplay mechanics as the previous 3 games (X-Wing, TIE Fighter, X-Wing vs TIE Fighter).
This game is a flight simulator game set in the Star Wars universe between 3 ABY (After Battle of Yavin) and concludes with the final events of Star Wars Episode 6. You play as “Ace” Azzameen, a member of a successful merchant family. In the story missions, you play through many family missions, and after certain events transpire, you end up joining the Rebellion and fighting for them.
The one weak point of X-Wing Alliance was the multiplayer- the online play never took off, and LAN play was buggy at best. However, this wasn’t a failing of the game as much as a failing of networking of the early 2000’s.
If you have the time (and the joystick), I highly recommend downloading a mod for your version of the game to make it compatible with your modern OS, and sinking hours into this game!