Have You Played? is an endless stream of game recommendations. One a day, every day of the year, perhaps for all time.
Still the flight sim I think most fondly of, with the possible exception of Stunt Island, but you should probably bear in mind that I'm a dumb-dumb stupid-head without the patience or manual dexterity for full-fat flight sims. Crimson Skies lifts me into the clouds because it's all about the fantasy of being a pilot, rather than the safety-first reality of it. Derring-do and loop-the-loops, otherworldly sights and spirits never lower than sky-high. The alt-30s, historical sci-fi setting is just icing on Crimson Skies' joyful cake.
I somehow didn't realise until now that it was originally the brainchild of Jordan 'Shadowrun' Weisman, who was also involved in BattleTech and Mechwarrior. Jeez guy, you've got a generation in your hands. Weisman's Crimson Skies was in fact a boardgame with little plane models, which to this day I would love to own. (There was a 2003 HeroClix-style game too, which I'm less interested in).
Anyway: Crimson Skies the game was styled like a Saturday morning matinee, and those perfect pilots with their lopsided smiles and Indiana Jones wit'n'grit, and that raw charm remains unusual in games to this day. I know Nathan Drake has his fans, but it doesn't quite work on me when the guy's actually superman: when it's a voice coming from an alt-reality areoplane which is really, really super-fantastic fun to fly, then I'm in love.