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I would have to agree with WhiteSilhouette. I would say the Tie Fighter series. =)
Il-2 Sturmovik FTW!
Mine was StarLancer, not sure why.
Never been much of a flight sim person, but have enjoyed the occasional Star Wars: Rogue Squadron back in the day. Probably closest I got.
IL-2 for a combat sim, MSFS X otherwise.
Probably FSX.
F19 Stealth Fighter. Some times the old ones are gold ones.
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Sielle: Wing Commander 2, by far. Ok so not so far in front of Freespace 2. :)

I forgot about the WIng Commander series! I really wish a new privateer would come out or GOG would hurry and re-publish the originals
Mine is Combat Flight Simulator 3: Battle for Europe. I picked up a new Joystick just so I could play this game back when it came out.
Does Freespace count?
Freespace is pretty awesome.
Jane's Fighters Anthology
So many planes, so many settings. It was an awesome compilation!
LHX Attack Chopper
Played it years over years.
Wing Commander III: Heart of the Tiger
More movie than flight sim (and more arcade game than flight sim.), but hey!
Wow - didn't expect to see so many F19 fans!
Hmmm. I'm not really keen on flight sims, but I'll say the original Red Baron (that's one of the few I've actually played... I'm seriously bad at simulators).
If space flight counts, then it's Freespace/Freespace 2.