Film Appreciation - Heaven Holds the Faithful Departed

Guest contributor Greg R. investigates the twists and turns of The Departed (2006) for Film Appreciation.

In 2005, Martin Scorsese was hired to direct a crime drama which followed two main characters, one a planted cop who worked as a mole for the mob while the other was an undercover cop trying to catch the mob.  Although Scorsese wasn't aware when he was hired, he was about to direct a remake of a Hong Kong film known as Infernal Affairs, this time called The Departed.

Originally, Tom Cruise and Brad Pitt were in line to play the two main characters, but both had to eventually back out of the project, with Pitt remaining as a producer on the project.  Eventually, the role of Billy Costigan, the undercover cop, went to Leonardo DiCaprio while the role of mafia mole Colin Sullivan was cast with Matt Damon.

The cast was then rounded out with Martin Sheen, Mark Wahlberg, Alec Baldwin, Vera Farmiga, and Jack Nicholson.  Shooting began in the spring of 2005 and the film was released on October 6, 2006.  It ended up winning four Academy Awards, including Best Picture, Best Director, Best Adapted Screenplay, and Best Film Editing, while also earning a nomination for Mark Wahlberg as Best Supporting Actor.

So, when I decided to write an article on a crime drama, The Departed was at the top of my list and, in my opinion, has always been worthy of its praise.

The film begins "several years ago" in Boston, as mobster Frank Costello (Jack Nicholson) encounters a young Colin Sullivan in a store and proceeds to buy his way into Colin's trust.  As we see over time, Frank molds Colin into the type of man he thinks can be beneficial to him on the inside of the police department.

It's well established in the opening scenes that mobster Frank Costello is a humongous scumbag.  He actually asks the girl behind the counter if she's had her period yet.  Jack Nicholson was apparently given free reign to improvise some of his lines, so it's no wonder he gets some of the most entertaining stuff to do.  He always plays bad guys with such glee.

The grown up version of Sullivan, played by Matt Damon, is sent to the police academy by Costello as a plant and claims his place in the city's brotherhood of blue after graduation.  Meanwhile, Leonardo DiCaprio's character, Billy Costigan, is also attending the academy with dreams of protecting the streets, but harboring the secret of having had family in the mob.

The part I find most interesting about this movie is the two lead characters, and how they are essentially spiritual doppelgangers of the other.

Both are then sent, separately, to Captain Oliver Charles Queenan, played by Martin Sheen, and Staff Sgt. Sean Dignam, played in a terrific turn by Mark Wahlberg.

The fact that Wahlberg garnered an Oscar nomination and kept a straight face while sporting this haircut is a testament to how far he's come as an actor from his days rapping with The Funky Bunch.

Sullivan is assigned to an elite task force run by Captain George Ellerby (Alec Baldwin) while Costigan gets ripped to shreds by Dignam and Queenan concerning his colorful family's mob history before being assigned to go undercover into the Costello organization because of his past family connections.

I'm not feeling the "Good Vibrations" from Wahlberg in this scene.  Dignam’s a very angry character and we’re not ever really sure why.  But, he's entertaining and that's all that matters.

Once Costigan gets out of prison, he establishes contact with his cousin Sean, played by Kevin Corrigan, to infiltrate the organization, while Sullivan begins his career pretending to help with the investigation into Frank Costello.

I find the way the two were brought into the academy telling of the journeys of their characters throughout their lives.  Sullivan gets brought into the academy with great support from higher-ups without much effort and is basically handed the keys to the kingdom.  Costigan works hard to get his badge and is immediately sent directly to prison to establish his cover while being basically forgotten and locked away with little support.

On an elevator, Sullivan has a friendly encounter with Dr. Madolyn Madden (Vera Farmiga), a police psychiatrist.  They flirt with each other a bit before Sullivan gets her name and number, wanting to set up a dinner date between the two.  They have dinner in an upscale restaurant.

Damon and Farmiga have good chemistry and play off of each other very well.  Farmiga has what I like to call "lady charisma", a presence that keeps the viewer captivated and makes it hard to look away from the screen when she appears.

Meanwhile, Costigan gets into a brawl with two mobsters and finds himself in a sleazy bar, where he encounters Costello, who offers him protection from their retaliation before interrogating him with a few shots to his already injured arm to make sure he's not a cop.

DiCaprio is great here and I honestly believed he was in pain during this scene.  Costello continues to be a sociopath with no redeeming qualities.

After Costello presents Costigan with the severed hand of a narc, Costigan disposes of any and all wires which Queenan and Dignam planted on him and tells them it's too risky.  He continues to get deeper and deeper into the organization with various acts of crime against Costello’s enemies while Sullivan spends his time having sex (or at least trying) with Madolyn and trying to find out who Queenan's undercover cops are.

It's implied that Sullivan may be impotent here.  Lady charisma isn't enough for him, I suppose.  DiCaprio continues to get the best material and really should have been promoted for an Oscar, but declined due to not wanting to compete with the rest of the cast.

Costigan, coincidentally, begins to see Madolyn professionally in order to talk about his feelings regarding his supposed expulsion from the police academy.  He possibly impresses her with his insight into the behavior of cops and her own personal background.  However, after an explosive confrontation over Costigan stating he wants Valium, the two of them argue and end up going out for coffee.

This is the only part of the movie I don't really think rings true.  Costigan acts like a total junkie, berates her in her office, and then she agrees to have dinner with her own patient?  Not likely in the real world.  But, at least Farmiga is charismatic while making what in a normal situation would be a bad decision.

Sullivan warns Costello about surveillance on his business transaction with some Chinese gangsters.  Sullivan, via cell phone, helps Costello get out of a meeting undetected.  At this point, it becomes obvious to Costigan that there is a leak in to the department.  Costigan also learns that Costello has been informing to the F.B.I. in order to get them to look the other way concerning his own activities.

Nice tension in the surveillance scene all-around.  Wahlberg is especially pissed off, generating my favorite line of the entire movie:  "I'm the guy that does his job. You must be the other guy."

Meanwhile, Madolyn becomes slightly suspicious of Sullivan after they move in together when Costello calls with a disguised voice.  As she is busy packing her things at her old house, Costigan shows up and they have sex.

I feel like Costigan and Madolyn could have used a few more scenes to develop their onscreen relationship to make this scene seem more realistic.  That, and they could have met a different way.  I think some time was supposed to have elapsed, but it's never really made clear how long the two knew each other.

Costello forces all of his crew to hand over their personal information, at which point he turns it over to Sullivan so that he can run background checks on everyone.  Costigan follows Costello to the exchange and then finds himself on Sullivan's trail.  Sullivan, reacting in a panic after he realizes he's being followed, kills an innocent man he mistakes for Costigan.

This was a nice little cat and mouse game for a brief moment.  It's the first time Sullivan begins to show some fear and vulnerability, leading to paranoia and eventually murder.

Costigan then meets with Costello at a bar and they discuss who could be the mole within the organization.

Great scene between these two as they play mind games with each other.  Nicholson hams it up a little as only he can.  This was, apparently, one of the most improvised and more memorable scenes in the movie.

Sullivan uses his power to have Queenan followed, citing to any questioning cops that he may be the mole within the department.  He meets with Costigan and Costello sends his men to find the mole.  Queenan tells Costigan to make a run for it, but while he does, Queenan is thrown from the roof to his death by Costello's men, landing at the retreating Costigan's feet.  This causes a gunfight between the mafia guys, a bullet wounding Costello's man, Timothy Delahunt.

A lot goes on during this scene and the death of Queenan is a major blow to DiCaprio's standing within the police department.  Now, only Dignam knows he's even employed by them.

In the aftermath, Dignam quits after refusing to work for Captain Ellerby.

So, much like in real life, no one wants to listen to Alec Baldwin.  Dignam essentially quits and leaves for parts unknown.  Hopefully, to find a barber.  But, with Dignam gone, Costigan is essentially an unknown factor to the police and no one can verify his status as undercover.

Delahunt succumbs to his gunshot wounds, but only after dropping a veiled hint as to him knowing Costigan is a cop.  It turns out Delahunt was also an undercover cop, as broadcast by the news after they find his body.  Sullivan calls Costigan on Queenan's phone and has a brief conversation before hanging up.  After Sullivan finds out from Queenan's diary of Costello's status as an F.B.I. informant, he begins to worry about his own status within the department and sets up Frank to be caught.  Costello's crew is taken out by the police while Sullivan personally kills Frank.

Sullivan is seriously beginning to unravel here and is becoming more and more paranoid as the movie goes on.  He is more than willing to kill anyone who threatens his secrets, even the man who handed him everything in his life.  Sullivan then takes credit for the raid.

Costigan comes in during the aftermath and has a meeting with Sullivan.  Sullivan ends up deleting Costigan's file after Costigan figures out that Sullivan is the mole and leaves the department in the middle of their debriefing.  Costigan takes a file to Madolyn and tells her to open it only if something should happen to him.

We're never definitively given any clue as to what was in the envelope, but I've always suspected that it was evidence against Sullivan and had an impact on the final scene in the movie, though it's never verified.

Madolyn later tells Sullivan that she's pregnant.  However, curiosity overcomes her when Sullivan receives a CD in the mail with Costigan as the return recipient, which contains a recording of a conversation between Costello and Sullivan, revealing him as a mole.  Madolyn listens to the CD and then leaves a pleading Sullivan.

Lady charisma has left the building.

Sullivan goes to meet Costigan and places him under arrest.  After a slight confrontation with former academy mate, Trooper Brown (Anthony Anderson), Trooper Barrigan (James Badge Dale) arrives on the scene and shoots Costigan in the head, killing him instantly, after which he kills Brown and reveals himself as a second mole in the department.  Sullivan quickly uses the opportunity to murder Barrigan and frame him for all of the mole's activities.

I was legitimately shocked when I first saw this scene.  It takes guts to kill the main character so suddenly and quickly without even a shred of foreshadowing.  Trooper Barrigan had only had a few scenes earlier in the movie, so it was a double surprise to see him do the killing.  Sullivan, as usual, has everything handed over to him with a little red bow.  He gets rid of Costigan, plus gets to frame Barrigan for all the of his mole actions from before.

At the funeral, Sullivan tries to talk to Madolyn, who blatantly ignores him.  As Sullivan returns home, he is met by Dignam, who shoots him in the head and leaves before the closing credits roll.

Sullivan's run of good luck finally ends.  Dignam's bad hair day doesn't.  People always debate how Dignam knew about Sullivan's mole status and I always go back to the envelope Costigan gave to Madolyn earlier before his death.  I'm assuming that there were instructions given to hand over evidence to Dignam in case of his death.  Dignam decides to take the law into his own hands and violently end Sullivan's duplicity once and for all.

This is probably my favorite crime drama of all-time.  It had a terrific cast, great writing, wonderful directing, nice suspense, a little action, a small love story, and a look into the souls of two men who operated in a world opposite of what was in their hearts.