F22 Total Air War (or TAW for short) - Released in 1998 I've ben playing it since then and still play it today.
It's a F-22 Raptor flight sim which has above average "flying" gameplay and "poor for now but great for 1998" graphics but what brings so many players back time and time again is the dynamic campaign system which is still the best system I've ever used in any game. Even after 25 years and what must be into 10,000+ hrs played I'm 100% sure I've never played the same mission twice. Whilst the general gameplay is based around flying an F-22, one of the best parts to the game is that it also allows you to play as the AWACS commander, effectively deciding the entire air warfare strategy for the various conflicts whilst also allowing you to jump in/out of various F22 cockpits "on the fly" to carry out their mission (or just going rogue) whilst controlling all the other friendly air asset's.
What I've love to happen, but never will, is for DCS level graphics to be ported across but for that to be the only change, literally nothing changed except better graphics. I think that if that game was released today, considering the lack of depth in "good/modern" flight sims, it'd do really well.