I know, I'm like a year and a half late, but I finally started playing Crimson Skies
on the Xbox. This game is fantastic, with a really intuitive flight model and control scheme. The production value is top notch (well, for late 2003), with excellent explosions, a respectable storyline, cut scenes that are worth watching, and best of all, nicely mixed 5.1 surround sound.
To top it off, Crimson Skies is a real blast to play on Xbox Live. I haven't had this much fun in an online dogfight since I played Red Baron back on the Sierra Network Online / INN. And that was over a decade ago!
I only wish it supported HD resolutions beyond 480p.
If you're like me and missed this game when it first came out, grab it now with the under $20 price tag, and meet me online!