* AllStarCast: The primary cast has some recognizable names in Hollywood most notably Creator/ColinFarrell, Creator/AngelinaJolie, Creator/ValKilmer, Creator/AnthonyHopkins, Creator/JaredLeto, Creator/RosarioDawson and Creator/ChristopherPlummer.
* CreatorBacklash: Creator/ColinFarrell seemed to feel this way even when the movie was still in theaters. When he hosted ''Series/SaturdayNightLive'' after the film's underwhelming premiere, he mentioned in his opening monologue that working on the film was "[[DeadpanSnarker time well spent]]." The awkward chuckles in the audience were priceless.
* CreatorKiller: Creator/OliverStone never truly returned to his former status after this.
* DawsonCasting: 75 year-old Creator/ChristopherPlummer as Aristotle, who was 61 at the time of Alexander's death.
* DuelingMovies: Came out within a year of three other historical battle epics that were attempting to follow on the success of ''Film/{{Gladiator}}'' -- ''Film/{{Troy}}'', ''Film/KingArthur2004'', and ''Film/KingdomOfHeaven''.
* DyeingForYourArt: Creator/ValKilmer gained over fifty pounds, and stopped working out, for the plump role of Philip.
* FakeNationality:
** You'll have hard time finding actual Greeks in this film. Most of the Greeks and Macedonians are played by non-Mediterranean actors, mostly Anglo-Saxons, who would have been classified as Celts at the time and place the story is set. Especial mention goes to Creator/AngelinaJolie, who has Native American blood of all things.
** Persians and Asians are usually played by Middle-Eastern actors, with the main exception being Roxana, who is played by the half-American, half-Afro-Latina Creator/RosarioDawson and accordingly has much darker skin than the real Roxana would have. Bagoas is another exception, although he's played by a Spaniard, who is dark enough to believably pass as an ancient Persian/Iranian, and the same could apply to Bessus and Stateira, played by French actors who are still more or less properly tan.
* FollowTheLeader: Creator/OliverStone was finally able to make the film about Alexander the Great he wanted to for years after the giant commercial and critical success of ''Film/{{Gladiator}}''.
* MagnumOpusDissonance: This was a dream project of Creator/OliverStone that became one of the worst received films of his career.
* NeverWorkWithChildrenOrAnimals: Creator/OliverStone claimed that the horses were more dangerous while filming the battle scenes than the elephants. The horses were often reckless with their riders, while the elephants were much more careful not to harm the actors.
* QueerCharacterQueerActor: Bagoas, traditionally considered a lover of both Darius and Alexander, is played by Francisco Bosch, who is homosexual in real life as well.
* UnderageCasting:
** 29 year-old Creator/AngelinaJolie as Olympias, who was fifty-two when Alexander died.
** Ptolemy was eleven years older than Alexander, but Creator/ColinFarrell and Creator/ElliotCowan were both the same age.
* WagTheDirector: Historical Consultant Robin Lane Fox, and the costume design team, originally planned for Creator/AngelinaJolie to be clothed exactly as a woman of Olympias' time and position would have appeared. This included a long dress and shawl that would have fully covered her entire body, including her hair. Jolie, however, objected strongly to this, and insisted her character be far less clothed to emphasize her sexual power.
* WhatCouldHaveBeen:
** The theatrical cut in its ultimate form was enforced by Warner Bros. and there was insistance to still trim it down some more, in the fear that a movie with a running time of nearly 3 hours will be too much for audiences. One can only wonder what it would be like if Stone was allowed to do it his way and go from the start with what ultimately became the "Revisited" cut, which runs for 215 minutes, swaps order of scenes and expands various subplots and characters beyond single-scene snippets (and is widely considered a very solid film, as opposed to the butchery released in cinemas).
** Creator/BazLuhrmann was planning his own Alexander the Great biopic at the same time starring Creator/LeonardoDiCaprio, but abandoned it when Stone beat him to the punch.
** Creator/HeathLedger was considered for Alexander.
** Stone's first choice for King Philip was Creator/LiamNeeson, who turned it down. Creator/SeanConnery and Creator/RussellCrowe were also offered the role. Neeson (52 at the time) and Connery (74 at the time) would have both been examples of DawsonCasting due to the historical Philip having died at 46.
** Creator/CatherineZetaJones was considered for Olympias.
** Creator/BradPitt was considered for Hephaestion, but turned down the role due to personal concerns with the character.
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