* AcclaimedFlop: The movie received a creditable 72% on Website/RottenTomatoes, but did not make up its budget.
* ActorAllusion: Creator/JudeLaw and Creator/GwynethPaltrow had previously played a couple in ''Film/TheTalentedMrRipley''.
* AwesomeDearBoy: ''In spades''. From Creator/JudeLaw getting to work with Creator/LaurenceOlivier [[spoiler:(sort of)]], to him and Creator/GwynethPaltrow signing on ''immediately after watching the demo reel'', to Creator/AngelinaJolie getting to wear an EyepatchOfPower and a goldfish-bowl space helmet.
* BillingDisplacement: A sterling example. Creator/JudeLaw and Creator/GwynethPaltrow are billed diagonally. On ''the same card,'' Jolie gets the "and" honor by being billed as "and Creator/AngelinaJolie". They thus manage a triple simultaneous diagonal bill where everyone gets a position of honor.
* BoxOfficeBomb: Budget, $70 million. Box office, $57,958,696. The film destroyed brothers Kerry (director and writer) and Kevin (production designer) Conran's careers — neither have done anything of note since.
* CastingGag: [[spoiler: Totenkopf turns out to have been DeadAllAlong, [[FakeShemp just like his actor]] Sir Creator/LaurenceOlivier, who died 15 years before the movie was made.]]
* CreatorBacklash: Kerry Conran was so devastated by the failure of the film that he refused to discuss the project for several years.
* CreatorKiller: The film destroyed brothers Kerry (director and writer) and Kevin (production designer) Conran's careers - neither have done anything of note since.
* FakeNationality: Englishman Creator/JudeLaw plays the American hero who's NotEvenBotheringWithTheAccent, while American Creator/AngelinaJolie plays British "Franky". Jolie's accent was mocked by some critics, though she's merely riffing on the stiff-upper-lip jargon of British war propaganda.
* PosthumousCredit: [[spoiler:Creator/LaurenceOlivier plays Totenkopf via archive footage. He died in 1989.]]
* RealLifeRelative: Jude Law's father, Peter, portrays Dr. Kessler.
* StarDerailingRole: While not as spectacular as usual examples, the failure of ''Sky Captain'' got Creator/JudeLaw relegated to playing supporting characters, rather than leads. It also killed all the momentum his career had at the TurnOfTheMillennium.
* StillbornFranchise: The film was going to spawn a franchise but since it became a BoxOfficeBomb, it never did. And even despite bombing, there was still interest in turning it into an anime series; that also never happened.
* WhatCouldHaveBeen:
** The Conran brothers asked for a budget of 3 million dollars and once stars got attached to the project, it was still a low figure of 20 million. With either of those budgets, the box office of 58 million would be considered successful. Kevin Conran himself is unable to answer [[UsefulNotes/HollywoodAccounting where the studio accounting added those extra 50 millions to his production]], because he never saw any of it.
** An anime series adaptation was in talks even after the film bombed, but eventually nothing came out of it.
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