During the 1990s and early 2000s a series of rival projects about Alexander the Great were decorating the desks of Hollywood’s biggest names. Oliver Stone emerged victorious with Alexander (2004), a much-maligned and sadly misjudged epic, but it all could have been very different…

Alexander III is a rich topic for dramatic adaptation; a battle-hardened bisexual who united Greece and Macedonia, conquered the Persian Empire, expanded its borders and introduced Hellenic culture to a wider world, all before his untimely death aged just 32. Despite his achievements he is also a divisive figure, seen by some as a satanic invader who despoiled a rich cultural history. He is the stuff of legend, and a legend worthy of film.

Christopher McQuarrie certainly thought so. In the late 1990s, after the success of The Usual Suspects, he and Seattle-based playwright and Alexander obsessive Peter Bushman began developing a script on the conqueror’s life, continually redrafting over a period of seven years. Like their subject, there were no boundaries to their ambition, as with rival projects circling in Hollywood and an immense budget required to fully realise Alexander’s story they were convinced their script would never be made: in McQuarrie’s words, “It’s doomed to fail”.

Nonetheless, some directors and studios showed interest in their venture – but bailed because of its immense scale, the lack of box office potential in ancient historical epics at the time, and McQuarrie’s insistence that if the film was made, he would be the one to direct it; note that until The Way of the Gun (2000), this $180-200million behemoth would have been his first film…

However, the success of Gladiator in 2000 inspired studios to invest in the classical world, and a number of projects went into development, including Wolfgang Petersen’s Troy. It was at this time that McQuarrie was contacted by a representative of Leonardo DiCaprio: the star had read the script, liked it, and wanted to make it. What’s more, with him on board European investors were prepared to fund it. But there was a catch: DiCaprio was only prepared to work with three directors, and McQuarrie wasn’t one of them.

But Martin Scorsese was.

The duo had just made Gangs of New York together and Scorsese also loved McQuarrie’s script, so the latter conceded to the legendary auteur, admitting “he’s an adequate substitute”.

McQuarrie, Bushman and his producer reportedly split a seven-figure sum for their Alexander script, and the production looked set to go ahead. However, with DiCaprio filming Spielberg’s Catch Me If You Can and development already underway on The Aviator with Scorsese straight after, the Alexander project had to wait. In that time Stone – who had dreamed of making a film on Alexander since the early 1970s – surged ahead and produced his own Alexander, starring Colin Farrell as the eponymous figure, and Scorsese’s project was shelved.

We can only speculate as to what Scorsese’s Alexander would have been like. His previous foray into the ancient world was the controversial passion project, The Last Temptation of Christ. Starring Willem Defoe as Jesus, Harvey Keitel as a Bronx-accented Judas and David Bowie as Pilate, the results don’t inspire confidence. Furthermore, his kinetic editing and elaborate tracking shots seem somehow more synonymous with the late 20th century settings of Goodfellas and Casino, as well as the obsessive eccentricities of Howard Hughes in The Aviator.

However, from Raging Bull through The King of Comedy, to Goodfellas, Casino and The Aviator, Scorsese has repeatedly examined the corrupting influence of fame, ambition, and power: all features that dominate Alexander’s character and story. The director even described the conqueror as having “had great charisma. Someone called him the first superstar.”

And what of Scorsese’s superstar? DiCaprio was an inspired piece of casting, as his stunning performance in The Aviator reveals: Howard Hughes, like Alexander, was an intense, obsessive and ambitious personality. According to Scorsese, Leo even looked the part, stating that “there is a bust of Alexander, and it bears an amazing resemblance [to DiCaprio]”.

Although famed for his urban crime dramas, the prospect of seeing Scorsese push himself with the conventions synonymous with the ancient historical epic is enticing to say the least. Alexander led his small army across desert plains and rivers, over mountains and through jungles, fighting against hundreds of thousands in epic battles involving cavalry, chariots and war elephants, as well as savage sieges and brutal guerrilla warfare. Scorsese’s Alexander would have been his biggest and most ambitious film to date, and a challenge worthy of the man himself.

While Stone’s film is too often misunderstood and derided (check out the excellent Alexander Revisited: The Final Cut) and other Alexander projects – including Mel Gibson’s HBO miniseries and Baz Luhrmann’s attempt, also with DiCaprio – failed to materialise, Scorsese’s film remains one of the great What Ifs of contemporary cinema. That said, the McQuarrie/Bushman script is still out there, and DiCaprio has largely retained his youthful looks… Maybe, just maybe, Marty and Leo could still find a way of bringing their Alexander to the big screen?

And that would be Great.

Did fortune favour the bold or would Scorsese have conquered Stone? Would Leo have been Great? Leave a comment and let us know (in Greek, if you like… )