By TeeJay Small
| Published
While we can all agree that Leonardo DiCaprio was long overdue for his Oscar award when he finally received it for The Revenant in 2015, the debate for his best performance continues to rage on to this day. Some say DiCaprio should have won an Academy Award for his work on films such as Django Unchained, The Wolf of Wall Street, or 2006’s Martin Scorsese directed The Departed. The latter serves as one of the greatest crime films of the 21st century and is currently available to stream on Hulu.
A Dream Team Of A-Listers
The Departed serves as the third of seven collaborative efforts between Martin Scorsese and Leonardo DiCaprio, and is an American adaptation of the 2002 Hong Kong film, Internal Affairs. After choosing to set the adaptation in Boston, Massachusetts, Scorsese decided to restructure the film to loosely adapt the true story of notorious Boston crime kingpin James “Whitey” Bulger.
After fleeing Boston and going into hiding in the mid 1990s, Bulger was listed as number two on the FBI’s most wanted list, second only to Osama Bin Laden.
The Departed features an all-star ensemble cast consisting of Leonardo DiCaprio, Matt Damon, Jack Nicholson, Mark Wahlberg, Martin Sheen, Alec Baldwin, Vera Farmiga, Anthony Anderson, and more, marking the film as a who’s who of A-list performers.
Brad Pitt also serves as a producer on the film, apparently purchasing the rights to the adaptation himself before handing over the director reigns to Martin Scorsese. The film also holds a special place in Scorsese’s filmography, serving as his only Oscar win among over a dozen well-deserved nominations.
More Cat And Mouse Than Tom & Jerry
The film follows a complex series of interweaving plot lines surrounding Boston’s criminal underworld, led by Jack Nicholson‘s Frank Costello, a fictionalized version of Whitey Bulger.
As Costello grooms his protege, Matt Damon’s Colin Sullivan, to become a spy inside the Massachusetts State Police, Leonardo DiCaprio’s Billy Costigan Jr. is recruited by a special task force to act as a man on the inside of Costello’s gang. To make things even more complicated, one of Costigan’s only allies within the police force is his department-appointed psychiatrist, Vera Farmiga’s Madolyn Madden, who is the girlfriend of Officer Sullivan.
Through a series of highly intense action sequences, Matt Damon and Leonardo DiCaprio engage in a game of cat and mouse, finding themselves each searching for one another around every corner without tipping their identity to the other. Soon thereafter, it is revealed how Costello was able to maintain a stranglehold on Boston’s crime world for so long unimpeded, adding another twist to the narrative.
Double Agents Double Crossing
The similarities between Costello and Boston mobster Whitey Bulger seem to come to a bloody end towards the film’s shocking conclusion. In reality, Whitey Bulger was killed by inmates hours after being transferred to a penitentiary in Hazelton, West Virginia at the age of 89 in 2011, 5 years after The Departed had been released. The fictionalized version of Bulger has a very different fate.
From this point in the film, the bloodshed continues, as droves of double agents working for both Costello and the state of Massachusetts begin locating and killing one another in an effort to protect themselves from a growing list of federal indictments, with Matt Damon and Leonardo DiCaprio at the center of it all.
The Departed was praised for its complex screenplay, nuanced performances, and incredible direction from Scorsese. Many film fans maintain to this day that the performance delivered by Leonardo DiCaprio in the film was the best of his career, building on the at-the-time popular trend of deriding the Oscars for not awarding the star his due Award for his long-celebrated acting chops.
The film received massive critical and audience success, amassing scores of 91 percent and 94 percent from critics and audiences, respectively on Rotten Tomatoes.
Following the success of The Departed, Martin Scorsese has since recruited Leonardo DiCaprio to lead in 4 more fantastic films, including Shutter Island (2010), The Wolf of Wall Street (2013), The Audition (2015), and Killers of the Flower Moon (2023). The pair have maintained an incredible working relationship together since first collaborating on 2002’s Gangs of New York, leaving audiences hopeful that the duo can continue to capture their magic in numerous films to come.
In the meantime, The Departed is streaming on Hulu as of this writing.
