Set in an alternate 1930s in which the plane and Zeppelin become the primary means of transportation, the game focuses on the adventures of Nathan Zachary, leader of the Fortune Hunters air pirate gang.

As a result of this overhaul, which delayed the game's publication to October 2003, several issues were addressed and new features added, most notably the addition of Xbox Live support.

Project lead Jim Deal explained that Crimson Skies was built around an arcade design to make the game easy to learn, and to place its focus on action instead of the physics of flight.

[6] There are over twelve playable fighter aircraft in Crimson Skies: High Road to Revenge, including planes available to download over Xbox Live.

[5] High Road to Revenge gives the player the ability to switch out of their current plane during gameplay and commandeer additional aircraft on the ground.

[7] The following multiplayer modes are available for the game out of the box: A player's online ranking in High Road to Revenge is based on their performance record, which includes wins and losses as per the Crimson Skies' Xbox Live scoring system.

This in turn caused the primary means of transportation to shift from the car and train to the plane and Zeppelin; consequently came the formation of air pirate gangs who plunder aerial commerce over North America.

[15] As a result of the events surrounding the world of Crimson Skies, advancements in technology within the game universe proceeded at a faster rate than actually occurred in the same era.

[17] Art director Robert Olson has stated that his team faced challenges in developing content that "fit the time setting" and was also "both fantastical and believable", particularly in the design of the game's bosses.

For example, Chicago was significantly redesigned for High Road to Revenge with the addition of avenues for aerial commerce among its skyscrapers and landing areas within the buildings themselves.

Thibodeaux (Jimmie Woods), the Cajuns' leader, attempts to claim Zachary's fighter and Zeppelin; Nathan, however, with the aid of Betty, another member of the Fortune Hunters, manages to recover them both.

He informs Nathan of what he believes had been the target of the attempted burglary: his plans to construct a wind turbine, a device capable of artificially generating storms.

He warns Nathan about Von Essen (Charles Dennis), a scientist who had unsuccessfully tried to engineer a wind turbine for a German superweapon earlier during the Great War.

When Nathan and the Fortune Hunters return to Fassenbiender's lab, they find it under attack from Die Spinne, a large group of planes with advanced weaponry.

Nathan, along with Betty (Tasia Valenza), Big John (Wally Wingert), and the other Fortune Hunters, embarks on a campaign to find those responsible and have them "brought to justice.

"[24] He and the Fortune Hunters travel to Arixo, seeking out a mine producing titanium, the only material that could be used to build the wind turbine; there, they hope to gain clues as to the identity of Doc's murderer.

[24] During his search, Nathan comes across Maria (Nika Futterman), who agrees to lead him to the titanium mine on the condition that she is allowed to join the Fortune Hunters.

The Fortune Hunters track Maria's movements southward to a "Lost City" in South America, which they identify as Von Essen's principal base of operations.

[27] Although Project Art Director Robert Olson complimented the radio play that frames the campaign of the previous title, he notes that a different presentation was needed for the game's new target audience.

[17] The development team decided upon an adventure along the vein of the Indiana Jones franchise, adding elements of "over-the-top, 1930's pulp-fiction style action", such as the game's boss battles.

[8] The style chosen by the developers led them to hire Drew Struzan, the artist responsible for the Indiana Jones film posters, to do the box art.

[9] When development of Crimson Skies: High Road to Revenge was first assumed by FASA Studio, it was conceived that the game be made into an "interactive movie",[29] a concept that would have involved an elaborate storyline and a large number of cutscenes.

[21] Programmer Patrick Schreiber later noted about the "playable movie" concept that "it looked great on paper, but […] was difficult to implement in a way where it felt like the player had some control over what was happening".

[29] The game's "interactive movie" concept was scrapped, the storyline simplified, and the original linear mission design was reworked to promote more choice-driven gameplay.

One example of this is the game's open-ended missions, which allow players to "explore the […] world of Crimson Skies: High Road to Revenge at their leisure".

[29] Another is the ability to substitute a fighter plane for a stationary weapon or another aircraft, which was added in order to give the player "different ways to accomplish the same goals".

According to Stan LePard, the soundtrack takes inspiration from various sources, including Errol Flynn swashbucklers and the concert music of Igor Stravinsky and Richard Strauss.

[35] In October 2002, Del Rey published the mass market paperback book Crimson Skies as an official tie-in to the Xbox game.

Although billed as a tie-in with the game, numerous main characters and prominent aircraft from the book do not make an appearance in High Road to Revenge.

[5][49][46] IGN said that "the freedom to fly […] in any direction and unleash tons of firepower on human opponents will want to make you hug your Xbox Live subscription",[4] and commended elements such the game's capacity for 16-player matches and the quality of downloadable content.