The Cinephile’s Journey: The Departed

Nathan Box
3 min readDec 3, 2022

Recommendation: 4/5 Stars

The Cinephile’s Journey is an attempt to watch and review every film that has won The Academy of Motion Picture Arts and Sciences Oscar for Best Picture.

Plot: “An undercover cop and a mole in the police attempt to identify each other while infiltrating an Irish gang in South Boston.” -IMDB

Review: Unlike a lot of other movies that seem to take home the award of Best Picture, there is no great lesson or insight to glean from The Departed. You will not walk away from this film as a more empathetic person with a better understanding of some long-ignored community. This is an award winner because it is an ode to great storytelling. Simple as that.

Before diving deeper, I must mention my only complaints about this film. The dialogue is a little too smooth. On multiple occasions, I thought to myself, no one talks like this. No one. Second, after all these years, I am still not crazy about the bloodbath ending of this movie. To me, it feels cold and contrived. On both counts, I know people who will defend the screenwriting of this film. Neither of my complaints distracts from the overall power of the film (which is saying something considering one of those complaints is the resolution of the story).

If one of my chief complaints about this film is how it ends, then how can I still consider it to be a near perfect movie? It begins with a stellar cast. Normally, a cast with this many A-list celebrities makes me nervous. This much talent has a way of folding under the weight of expectation. Not here, and it begins with Jack Nicholson as Costello, the kingpin of South Boston. Nicholson’s performance in this film is menacing, maddening, and enthralling. You will hang on to his every word (no matter how offensive).

Second, the core of this story is strong. The bulk of the movie focuses on Leonardo DiCaprio as Billy, a Boston police officer who works to infiltrate Costello’s crew, and Matt Damon as Colin, a Boston police officer who is on Costello’s payroll. As both men sow seeds of distrust and play spies for the other side, this movie becomes a tale of cat and mouse as the cops face close calls and become consumed by the constant need to lie. When the yarn finally comes undone, it does in the most violent fashion.

From every angle, death abounds in this film. Without a doubt, Director Martin Scorsese’s fingerprints are all over this thing. As its last chapter unfolds, you must decide how the ending lands for you. In the end, this movie is not supposed to make you feel good. You aren’t supposed to learn anything. You are supposed to fall back in love with the power of storytelling for the sheer joy of telling stories.

Be good to each other,