{"id":9822,"date":"2026-08-17T13:52:22","date_gmt":"2026-08-17T17:52:22","guid":{"rendered":"https:\/\/kawsachunnews.com\/w\/brad-pitt-almost-starred-in-a-top-2000s-thriller-heres-why-he-passed\/"},"modified":"2026-08-17T13:52:23","modified_gmt":"2026-08-17T17:52:23","slug":"brad-pitt-almost-starred-in-a-top-2000s-thriller-heres-why-he-passed","status":"publish","type":"post","link":"https:\/\/kawsachunnews.com\/w\/brad-pitt-almost-starred-in-a-top-2000s-thriller-heres-why-he-passed\/","title":{"rendered":"Brad Pitt Almost Starred in a Top 2000s Thriller\u2014Here’s Why He Passed!"},"content":{"rendered":"
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Brad Pitt and Leonardo DiCaprio could have starred together 13 years earlier than in \u201cOnce Upon a Time\u2026 in Hollywood,\u201d but Pitt turned down a major role in this Martin Scorsese masterpiece for a specific reason.<\/p>\n

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It wasn\u2019t until 2019 and Quentin Tarantino\u2019s Once Upon a Time\u2026 in Hollywood that Brad Pitt and Leonardo DiCaprio truly shared the screen in a feature film. However, this collaboration could have occurred thirteen years earlier under the direction of Martin Scorsese.<\/p>\n

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Interestingly, Brad Pitt<\/span> was not just considered for a role; he was actively involved in the initial stages of the project. The film in question was none other than The Departed, which became one of Scorsese’s major hits and a defining crime film of the 2000s.<\/p>\n

Brad Pitt, the Driving Force Behind the Project<\/h2>\n

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The journey began in 2003. Along with Warner Bros. and producer Brad Grey, Brad Pitt<\/span> acquired the rights to adapt the Hong Kong thriller Infernal Affairs, which had been released the previous year.<\/p>\n

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The project gradually took shape, and William Monahan was brought on board to write the screenplay. When Martin Scorsese<\/span> finally joined the project, the original idea was to cast Brad Pitt<\/span> and Leonardo DiCaprio<\/span> as the two central characters.<\/p>\n

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However, Pitt eventually reconsidered his role in front of the camera. He felt that the story worked better with younger actors portraying these men at the beginning of their careers. He explained his reasoning in a 2007 interview with Interview Magazine:<\/p>\n

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\u201cI developed it for two and a half years. We fought for this film, and then we got William Monahan to [write] the screenplay. Once [Martin] Scorsese got involved, I thought it would be better with young guys starting out, guys fresh out of the academy, guys who are hungry. I thought I was too old for that.<\/i>\u201d<\/p>\n

Matt Damon Ends Up Taking the Role<\/h2>\n

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Brad Pitt<\/span> ultimately decided not to act in the film, although he stayed on as a producer. It was Matt Damon who ended up playing the role of Colin Sullivan opposite Leonardo DiCaprio<\/span>.<\/p>\n

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In The Departed, the two men operate on opposite sides of the law. Billy Costigan (Leonardo DiCaprio<\/span>), a young cop with a troubled past, goes undercover in the heart of Boston’s mafia. His mission: to get close to Frank Costello, the formidable mob boss played by Jack Nicholson.<\/p>\n

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Meanwhile, Colin Sullivan (Matt Damon<\/span>) has a promising career in the police department but secretly works for Costello. Two moles find themselves on opposing sides, each trying to uncover the other’s identity before their own cover is blown.<\/p>\n

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Brad Pitt\u2019s decision did not prevent the film from achieving remarkable success. Released in 2006, the thriller earned Martin Scorsese<\/span> his long-awaited Oscar for Best Director. The film also won awards for Best Picture, Best Adapted Screenplay, and Best Editing.<\/p>\n

Brad Pitt Chooses a Different Path<\/h2>\n

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While Leonardo DiCaprio<\/span> and Matt Damon<\/span> were filming with Scorsese, Brad Pitt<\/span> chose a different direction. In 2006, he starred in Babel, directed by Alejandro Gonz\u00e1lez I\u00f1\u00e1rritu, alongside Cate Blanchett.<\/p>\n

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This decision proved to be quite successful: his performance in the film earned him a Golden Globe nomination for Best Supporting Actor.<\/p>\n

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The paths of Pitt, DiCaprio, and Scorsese would cross again a few years later in an unexpected way. In 2015, the three stars participated in The Audition, a short promotional film directed by Scorsese. However, it was not the major film featuring Pitt and DiCaprio that some might have hoped for.<\/p>\n

It Took Tarantino to Truly Bring Them Together<\/h2>\n

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The on-screen meeting finally occurred in 2019 thanks to Quentin Tarantino<\/span>. In Once Upon a Time\u2026 in Hollywood, Leonardo DiCaprio<\/span> plays Rick Dalton, an actor whose career is on the decline, while Brad Pitt<\/span> plays Cliff Booth, his stunt double and loyal friend.<\/p>\n

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Thirteen years after the missed opportunity with Scorsese, their collaboration became one of the main selling points of the project. The film was a hit, earning ten Oscar nominations and winning two awards. Brad Pitt<\/span> notably won the award for Best Supporting Actor for his portrayal of Cliff Booth.<\/p>\n

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It took more than a decade for the two actors to finally star together in a significant film. And while Brad Pitt<\/span> has never publicly regretted letting Matt Damon<\/span> take his place in The Departed, his refusal ultimately contributed to giving Scorsese’s masterpiece the cast it is known for today.<\/p>\n

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To (re)discover these two films, The Departed is currently available for streaming on Sooner, while Once Upon a Time\u2026 in Hollywood is accessible on Prime Video and HBO Max.<\/b><\/p>\n

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AlloCin\u00e9 offers over 40 daily articles on cinema and TV series news, interviews, streaming recommendations, and fascinating facts about your favorite films and series. Subscribing to AlloCin\u00e9 on Google Discover ensures you explore the richness of a site designed by enthusiasts for enthusiasts every day.<\/i><\/p>\n

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Add Allocin\u00e9 to your favorite sources Follow us Share this article WAwhatsapp FBfacebook TWtweet Brad Pitt and Leonardo DiCaprio could have starred together 13 years earlier … Continue Reading →<\/a><\/p>\n","protected":false},"author":17,"featured_media":9823,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[14],"tags":[],"class_list":["post-9822","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-tv"],"yoast_head":"\nBrad Pitt Almost Starred in a Top 2000s Thriller\u2014Here's Why He Passed! - Kawsachun News -<\/title>\n<meta name=\"robots\" content=\"index, follow, max-snippet:-1, max-image-preview:large, max-video-preview:-1\" \/>\n<link rel=\"canonical\" href=\"https:\/\/kawsachunnews.com\/w\/brad-pitt-almost-starred-in-a-top-2000s-thriller-heres-why-he-passed\/\" \/>\n<meta property=\"og:locale\" content=\"en_US\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"Brad Pitt Almost Starred in a Top 2000s Thriller\u2014Here's Why He Passed! - Kawsachun News -\" \/>\n<meta property=\"og:description\" content=\"Add Allocin\u00e9 to your favorite sources Follow us Share this article WAwhatsapp FBfacebook TWtweet Brad Pitt and Leonardo DiCaprio could have starred together 13 years earlier ... 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