After having five of his films nominated for Best Picture since 1976, Martin Scorsese finally broke through and won Best Picture with The Departed, which was a remake of a Hong Kong film called Internal Affairs. Over the previous 30 years, Scorsese deservedly built up a reputation for being one of American cinema’s great directors. He was and is a man who could direct any style of film and direct it well. All you need to do is look at his previous nominees (Taxi Driver, Raging Bull, Goodfellas, Gangs of New York, and The Aviator), not to mention his other amazing films that weren’t nominated (The Age of Innocence, Hugo, Kundun, The Wolf of Wall Street, etc.) to understand the wide variety of material that Scorsese has mastered. Yet even with that wide variety of material, Scorsese has a signature style of filmmaking that is as unique to him as are his fingerprints.

I would say from that perspective that The Departed might be, along with The Age of Innocence and Kundun, one of the most un-Scorsese like films that Scorsese has made. Scorsese has a lot of signature motifs that he often spreads throughout the film at key moments. He quite often will have a long trucking shot that follows a character through a location or a series of locations. He also will change the speed of the film in order to create some point of emphasis within his shots at strategic points throughout his films. Many of his films are also littered with moments of graphic violence.

The Departed lacks the long trucking shots. It does have moments of varying camera speeds, but they’re much more subtle in this film than in others. And while there is certainly a fair amount of graphic violence in The Departed, it doesn’t feel as gratuitous as it does in other Scorsese films. Do I think that The Departed is Scorsese’s best film? I do not, but it does rank very high for me in Scorsese’s pantheon. The Departed is a film that has it all. It’s got brilliant acting, tense and dramatic storytelling and it has a grey and somber look to it that is emblematic of the gray area between the right side of the law and the wrong side.

That last bit, to me, is the strongest aspect of this film. The Departed has a deep and complex set of circumstances. It’s a film that blurs the line between right and wrong and between good and evil. It’s a film that puts its two main characters, Billy Costigan (Leonardo DiCaprio) and Colin Sullivan (Matt Damon) into the camps of the enemy, and each has to discover who the other one is before it’s too late. Billy comes from a rough background with a father who was well known to both the police and the mob. He graduated from the Academy and was immediately given the assignment by Sgt. Dignam (Mark Wahlberg) and Lt. Queenan (Martin Sheen) to get himself arrested and spend the next couple of years in prison so that when he gets out he can infiltrate the gang of Frank Costello (Jack Nicholson), the most notorious gang boss in Boston, and the number one target of the Massachusetts State Police.

Meanwhile Colin has also graduated from the Academy and has unprecedentedly been assigned a plain-clothed position as his first assignment. Since he was a kid, he’s been involved with Costello’s gang, and now Costello has arranged for him to work as an informant from the inside, and Colin does his job well. He’s always able to get word to Costello that the heat is on, allowing Costello to make arrangements that allow him to continue to do his business without getting ensnared in the cops’ net. However, both Costello’s organization and the State Police realize that they have rats in their midst and both Billy and Colin can feel the nooses around their respective necks getting tighter and tighter. As the pressure mounts, Billy and Colin both become more desperate to get out of their respective situations and they also come to realize that their superiors either don’t have their best interests at heart or they’re unable to protect them adequately.

The Departed is an incredibly layered story. William Monahan won the Oscar for Best Adapted Screenplay for penning this script, and he deserved it without a doubt. If you’re a screenwriter working on a crime story or a heist story, this is a script that you should study. The complexity of the story lies in the fact that you have two characters in Billy and Colin who are mirror images of each other and trying to track each other down. Here’s where we get to the theme. The spine of this story is dealing with the gray area between good and bad as well as between right and wrong. The mob and the police operate under similar hierarchies and have similar rules within their organizations. They’re also both ingrained with violence as a means of getting what they want and need. The only difference is that one organization is operating outside the law and the other organization is working on the law’s behalf.

At the center of this conflict are Billy and Colin. They’re two guys with similar backgrounds who join the police force for two different reasons. Colin joined the police specifically to work as an informant on behalf of his boss Costello. He’s the ultimate insider and he uses his position within law enforcement to break the law at the highest levels. Billy, on the other hand, joins the police to put the lawlessness of his family history behind him. Ironically, he’s assigned to infiltrate Costello’s organization by becoming a criminal and diving back into the lifestyle that he wanted to leave behind. He works his way in to the organization as a means of breaking it down from the inside.

Monahan and Scorsese did a marvelous job of building this web of intrigue so that this story is so much more than the violence that fills the plot. This is a violent movie, but unlike Gangs of New York, Casino or even, dare I say Goodfellas, The Departed weaves an intricate and complex story that is not difficult to follow. Anyone can write a script that has a million things going on and anyone can make a film that is complex but also confusing. Monahan wrote and Scorsese directed a film that has a lot going on and is complex in nature, but also is told in a way that is easy to follow so that the audience gets the most out of the dramatic nature of the story.

Not only is this a well-told story, but the acting in it is also sensational. There are a bunch of character actors in this film that give exceptional performances and there are also a lot of big stars who might not be in roles that are the size they’re used to, but nevertheless give outstanding performances. Alec Baldwin is very funny as Captain Ellerby, a gruff Bostonian who’s blunt, no-holds-barred way of interacting ads personality and depth to the whole film. Vera Farmiga is the psychologist who starts dating Colin while also working as Billy’s court-appointed therapist. The fact that these adversaries share the same love interest adds tension and drama that lasts through the story right up to the penultimate scene.

But this is another movie that belongs to Jack. Jack Nicholson joined the select group of actors who’ve starred in three Best Picture winners (One Flew Over the Cuckoo’s Nest & Terms of Endearment), joining Clark Gable, Talia Shire, Diane Keaton, John Cazale, Dustin Hoffman, and Morgan Freeman to make up what I affectionately call the 3-Timers’ Club. And with 21 years between his first Best Picture winner and his third, his films spanned the longest amount of times between wins. It’s fitting to me that Jack joins this group, as he is one of the most popular and most iconic actors in the history of cinema, and Frank Costello is a role that he was born to play. It should be up there with Jake Gittes, R.P. MacMurphy, Col. Nathan Jessup, and Jack Torrance as his signature roles. Jack can bring depth to a character unlike most other actors. As I mentioned when discussing R.P. MacMurphy, Jack brings panache to roles that a lot of other actors can’t pull off. That panache makes what should be unlikable characters into likable ones and turns anti-heroes into folk heroes. We shouldn’t like Frank Costello. He’s a murderous gangster who appears to be ready to sell out his own country to make a few extra bucks. He’s ruthless and lethal and doesn’t care how much pain he inflicts on his enemies. However he’s loyal to those that show him loyalty and he has a devil-may-care attitude that humanizes him and brings depth to the story.

Some people have suggested that Costello is also loosely based on the character of Whitey Bulger, a notorious Boston mobster from the 1980’s, and that makes sense. Over the course of his career, Scorsese has done an excellent job in films like Taxi Driver, Goodfellas, Gangs of New York, and The Wolf of Wall Street into making New York City into one of the film’s characters. The attitude and grit of New York City comes out in those films and helps drive the story and develop the characters the way few cities outside of Los Angeles have done in movie history. In The Departed, Scorsese was able to do the same thing with Boston, much the same way his star Matt Damon did nearly a decade earlier in Good Will Hunting. Boston is an interesting city. It’s the heart of higher education and medical research in this country, but it has a sarcastic edge to it as well as a blue-collar grit that can rival any city. Like New York and like Los Angeles, Boston is an attitude just as much as it is a place, and Scorsese brought that attitude out in his characters and in the story so the fact that the film took place in Boston is as integral a part to this story as any of the other components. The Departed would have been a completely different movie in any other setting.

Did the Academy get it right?

I believe they did, although there were some fine films nominated against it. I would not consider Babel to be one of those films. It’s decent enough, but similar to the previous year’s Crash, it’s an ensemble piece with several different seemingly unrelated stories coming together with a common spine at the end. The difference is that these stories are taking place simultaneously all around the world, but the nature of it is the same. I enjoyed Letters From Iwo Jima, and I especially liked the fact that it was told from the Japanese perspective, as it’s not often that we get that point of view. Little Miss Sunshine took home the Oscar for Best Original Screenplay, and it’s a wonderful film in an indie film kind of way. It’s a feel-good film about family and what people will do to perpetuate the image that their lives and families are stable when in actuality they’re completely falling apart. From a recognition standpoint, getting nominated was as good as win for Little Miss Sunshine, but it wasn’t the best film of the year. The Queen is the type of sophisticated English film that might have won had it come out about five years later, and it’s a very good film in its own right. I remember being somewhat skeptical going into it, but then being pleasantly surprised at the end. It’s an emotional and thoughtful film that re-introduced American audiences to Helen Mirren, and gave a look to Queen Elizabeth II that was deeply and unexpectedly personal. This is a film that could have won, and I would have had no complaint. But it was The Departed that took home the Academy’s top award that night, and with its deep and complex story, the captivating and riveting performances by its actors and the thoughtful and well-crafted thematic elements that went into it, The Departed was the Best Picture of 2006.