Brad Pitt Almost Stole Leonardo DiCaprio’s Most Career-Defining Role in $406M Martin Scorsese Movie – How Did Leo Win That War

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Losing roles in a Martin Scorsese film isn’t anything new for Brad Pitt, with one notable example being the role of Colin Sullivan in The Departed, which also starred Leonardo DiCaprio. But apart from the critically acclaimed crime drama that earned Martin Scorsese his first Oscar, Pitt also lost playing the lead in Scorsese’s acclaimed movie based on the controversial figure, Jordan Belfort.


Before making its way onto the big screens, the adaptation of Belfort’s memoir The Wolf of Wall Street went through a steep climb to get greenlit by the studios. And alongside Leonardo DiCaprio, who eventually took the project under his belt, Brad Pitt also showcased a keen interest in adapting Belfort’s memoir.

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Brad Pitt
Brad Pitt

Leonardo DiCaprio Settled Score With Brad Pitt After Winning The Wolf of Wall Street

Back in 2007, Brad Pitt‘s production company engaged in a bidding war with Leonardo DiCaprio via their respective studios for the rights to Jordan Belfort’s memoir, The Wolf of Wall Street. Like DiCaprio, the Seven Star was also interested in taking the role of the controversial figure, but in the end,  the Titanic Star secured the project, describing it as “a modern-day Caligula.” 

Leonardo Di Caprio in Wolf of Wall Street
Leonardo Di Caprio | The Wolf of Wall Street

But this isn’t the lone time the two of the most beloved A-listers in the acting realm faced each other to get their hands on a beloved IP. Before The Wolf of Wall Street took the industry by storm with its release in late 2013, Brad Pitt’s Plan B and Leonardo DiCaprio’s Appian Way engaged in a competitive bidding war for World War Z, which went in Pitt’s favor. However, it won’t be a hot take to say that DiCaprio got a much better deal, as even though World War Z did better at the box office, Scorsese’s The Wolf of Wall Street was way more stronger and impactful.

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World War Z (2013)
World War Z (2013)

Winning the Bid Against Brad Pitt Was Only Half the Work for Leonardo DiCaprio

Despite being on the winning side of the bidding war, Leonardo DiCaprio’s The Wolf of Wall Street would be put on ice for several years down the line. From the 2007 Writer Strike to Martin Scorsese initially leaving the project, the project suffered notable delays before eventually picking up steam after Red Granite came into the picture. Considering the story was R-rated, DiCaprio struggled to find financers, and after Red Granite Productions agreed to finance the project and gave them full creative freedom, Scorsese rejoined the project.

“You know, it’s a hard R rating. This film was not easily financed. We had one opportunity to finance it [at a much lower budget], and then many, many years down the line, we found the right financiers, and Red Granite basically said to us: ‘Here’s the budget. We want an epic that pulls no punches. We don’t want to limit or censor anything.’ Ultimately, that was attractive to Marty getting back on board… ”  DiCaprio explained.

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Leonardo DiCaprio in The Wolf of Wall Street
The Wolf of Wall Street (2013)

While it’s reasonable to assume that Brad Pitt would’ve delivered an exceptional performance as Belfort, it’s hard to see anyone surpassing what Scorsese and DiCaprio achieved with this project.


The Wolf of Wall Street is available to stream on Paramount Plus.

Source: The Hollywood Reporter

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Written by Santanu Roy

Articles Published: 1588

Santanu Roy is a film enthusiast with a deep love for the medium of animation while also being obsessed with The Everly Brothers, Billy Joel, and The Platters. Having expertise in everything related to Batman, Santanu spends most of his time watching and learning films, with Martin Scorsese and Park Chan-wook being his personal favorites. Apart from pursuing a degree in animation, he also possesses a deep fondness for narrative-driven games and is currently a writer at Fandomwire with over 1500 articles.