- Adaptation Inspiration: While the original board game and the first video game had a relatively consistent technology level, the Xbox game, High Road to Revenge, takes the Diesel Punk vibe Up to Eleven with Spider Mechs, giant flying fortresses capable of eating entire zeppelins and Tesla weapons. By comparison, in the board game, Nikola Tesla is said to be working on a new type of engine, but he doesn't have a working prototype yet.
- Crowning Moment of Awesome: NVIDIA refused to release a patch to fix the unplayability of Skies on their newer drivers/cards, claiming that it was 'impossible'. The community went to a modder going by the handle 'Timeslip', who came back with a perfectly-working patch/fix in less than twenty-four hours. (The nature of the problem required an ad-hoc solution that likely wasn't possible, or was at the very least difficult to implement, by tinkering with drivers).
- Crowning Moment of Funny: Nathan's one-liners when shooting down enemy planes, or just blowing stuff up in general.
(blowing up a propane tank) "Oh, the humanity!"(shooting down an enemy fighter) "Couldn't count to twenty without taking his shoes off!" and "When you hit the ground, tell 'em Nathan Zachary sent you!"(meeting Ace Dixon again) "How many times have I shot you down, anyway?"
- Crowning Music of Awesome: EVERYWHERE.
- Demonic Spiders: Downplayed with the Hoplite gyrocopters. Though their appearance doesn't necessarily mean an automatic defeat and loss of hope, they are the most maneuverable aircraft in the game with good weaponry and armor to boot with only their slow speed preventing them from becoming Game Breaker enemies.
- Germans Love David Hasselhoff: Pirate's Gold and Rogue Flyer were supposed to be the first novels of two trilogies: Wings of Fortune and Wings of Justice. Despite the books being fully written, only these two were published in English. In Germany, however, Crimson Skies proved popular enough to warrant the publication of all six novels.
- Magnificent Bastard: Johnathan "Genghis" Kahn is this in spades. Nathan Zachary has his moments too.