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Leonardo DiCaprio and Martin Scorsese have collaborated on a number of projects together as actor and director. Beginning their partnership withGangs of New York, the duo went on to work on films such asThe Aviator, The Departed, Shutter Island, The Wolf of Wall Street, and the recentKillers of the Flower Moon. The duo are also rumored to collaborate again on a Frank Sinatra biopic.

Leonardo DiCaprio in The Aviator

While the two have worked together on many projects, they have also developed projects that have never seen the light of day. One of those was apparently a biographical drama on Alexander, The Great. The two never got to make it, but the duo may have no regrets about it as Colin Farrell’s version of the film ended up almost costing the actor his career.

Leonardo DiCaprio And Martin Scorsese Almost Developed A Movie On Alexander

Leonardo DiCapriohas worked with Martin Scorsese on many projects that have seen the light of day and have received positive responses. Scorsese won his first Oscar for Best Director withThe Departed, which starred DiCaprio along with Matt Damon and Jack Nicholson. The actor has been nominated for an Oscar twice while starring in a Scorsese film.

“DiCaprio doesn’t look like Sinatra”: How Leonardo DiCaprio Fans are Shutting Down Haters as Martin Scorsese Gears up for Biopic

The two share a wonderful working relationship that has spanned decades and have even closely developed multiple projects. DiCaprio revealed during the release ofThe Aviatorthat the two were also interested in developing a film based on Alexander, the Great. He said that both of them were interested in historical figures and their biographies and had received a screenplay that they were trying to develop.

In an interview withBlack Film, DiCaprio mentioned that as they were working on both, the script for the Howard Hughes biopic progressed faster and hence the film got made. By then, Oliver Stone had already made a film with Colin Farrell. DiCaprio said,

“DiCaprio doesn’t look like Sinatra”: How Leonardo DiCaprio Fans are Shutting Down Haters as Martin Scorsese Gears up for Biopic

“Alexander The Great was also, like I said before, it’s one of those things where Scorsese and I just share the same taste in similar things. We were both fascinated with Alexander The Great as well as Howard Hughes…It just happened to be that this script and the project were way further advanced in the development stage than the script that landed in our lap from Alexander and we wanted to go forth – we had an intention at one time of doing them both, but you don’t get everything you want all the time.”

DiCaprio also mentioned that he looked for other filmmakers to take on the mantle whileMartin Scorsesewas busy withThe Aviator, such as Baz Luhrmann. However, Oliver Stone beat them to it.

Martin Scorsese in The Audition

Colin Farrell’sAlexanderWas A Critical And Commercial Disaster

While it is not confirmed whether it was the same project, Leonardo DiCaprio and Martin Scorsese seemed to be too late to get their Alexander film made asJFKdirector Oliver Stone was way ahead of them. DiCaprio mentioned to Black Film that it was just how Hollywood worked and that many were developing similar topics at the same time. He said,

“There was, a lot of people were toying with it, that’s the way it is in the business, that an idea pops up and all of a sudden it’s a piranha feeding frenzy. Oliver got his off before anybody else’s.”

Colin Farrell in Alexander

However, DiCaprio may not have any regrets about giving it up as the resulting filmAlexanderended up being a critical and commercial failure. TheColin Farrellstarrer was criticized for its historical inaccuracies and long runtime and only earned $167 million against a $150 million budget (viaThe Numbers).

“I can’t work here anymore”: Martin Scorsese’s Only Oscar Winning Movie Soured His Relation With WB Because Studio Wasn’t Happy With the Ending

Farrell mentioned in a roundtable withTHRthat the film’s failure made him rethink everything as an actor as he was completely sure that it would fetch him an Oscar nomination. He said,

“When I say ‘expectation,’ we all had our tuxedos ready [for awards shows]. I’m not even joking. We were all like, ‘Right, lads, we’re off to the Oscars. This is a sure thing.’ And then it came out. The reviews came out, and I remember someone going, ‘Oh God, it’s not good’…This is not to apologize — I was a young man — but Alexander really made me go, ‘I don’t know.’ And what I had to do was plug back into the Colin that went into an acting class when he was 17.”

“I can’t work here anymore”: Martin Scorsese’s Only Oscar Winning Movie Soured His Relation With WB Because Studio Wasn’t Happy With the Ending

Despite starring stalwarts such as Angelina Jolie, Colin Farrell, Val Kilmer, and Anthony Hopkins, and Oliver Stone attached to the film, it seemed to have lost its way during the making.

Alexander The Greatis currently streaming on Apple TV+.

Nishanth A

Senior Writer

Articles Published :2416

Nishanth A is a Senior Entertainment Writer at FandomWire, majorly focusing on TV shows with over 2,000 articles published. He has been an entertainment journalist for the past two years and a scriptwriter at various corporations before that, working on educational content. With a Communications, English Literature, and Psychology triple major, Nishanth usually covers news and analyses on Star Trek, particularly Strange New Worlds and The Next Generation; Doctor Who, the DCU, and more.A Nolan fan, Nishanth spends his time exploring the filmographies of various directors with an auteurial style or can be found making short movies of his own. He has also contributed as a feature writer for Film Companion, focusing on the South division.

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Leonardo DiCaprioMartin Scorsese