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The Departed (2006)

TL;DR: The Departed (2006) rates 9 out of 10 on the rewatch scale. Scorsese’s 2006 Boston crime thriller. Two moles, one in the mob, one in the police.
The Departed (2006)
9 / 10

Official trailer

The Departed is the Martin Scorsese-directed crime thriller that became Scorsese’s first Academy Award winner for Best Picture and Best Director. Scorsese directed. William Monahan wrote the screenplay, adapting Andrew Lau and Alan Mak’s 2002 Hong Kong film Infernal Affairs. Leonardo DiCaprio plays Billy Costigan, a Massachusetts State Police trainee placed undercover in Frank Costello’s Irish-American crime organization. Matt Damon plays Colin Sullivan, the South Boston native whom Costello has groomed to infiltrate the Massachusetts State Police. Jack Nicholson plays Frank Costello, the South Boston crime boss.

Mark Wahlberg plays Sergeant Dignam. Martin Sheen plays Captain Queenan. Vera Farmiga plays Madolyn Madden, the police psychologist romantically involved with both Costigan and Sullivan. Ray Winstone plays Mr. French, Costello’s lieutenant. Alec Baldwin plays Captain Ellerby. The plot follows the two infiltrators’ parallel attempts to identify each other while pursuing their respective missions.

The Departed is Scorsese having a ball, and it’s infectious. Two rats in one city, each hunting the other, is about as good a premise as a crime picture can have, and I think the film squeezes every drop of tension out of it. DiCaprio is the one I can’t take my eyes off, a cop coming apart at the seams. It’s a 9 for me, and Nicholson’s excesses and a crowded second act are what keep it from climbing higher.

The film made approximately two hundred and ninety million dollars worldwide on a ninety million dollar budget. The commercial performance was strong. The film won four Academy Awards including Best Picture, Best Director (Scorsese’s first in this category after multiple nominations), Best Adapted Screenplay (Monahan), and Best Film Editing (Thelma Schoonmaker, her third Scorsese collaboration win). The Departed is consistently cited among the major American crime films of the 2000s.

The film’s specific position in the Scorsese filmography (the first Best Picture and Best Director after decades of recognition denied to films now considered superior) has been the source of ongoing critical conversation.

The Dual-Infiltration Structure

The film’s structural foundation is the dual-infiltration premise. Billy Costigan is the cop undercover in the crime organization. Colin Sullivan is the criminal undercover in the police department. Each man is hunting the other while pretending to be the other. The structural symmetry is the film’s central engine. Every scene works on the understanding that one of the characters in the room isn’t who he’s pretending to be. The audience knows both secrets. The characters don’t. The dramatic irony powers the film for two and a half hours.

The dual structure also produces moral complications. Costigan’s damage from prolonged undercover work is the film’s primary character arc. Sullivan’s psychological compartmentalization is the secondary character study. The film argues that both kinds of infiltration produce real harm to the infiltrator regardless of which side they’re working for.

Costigan’s exhaustion and Sullivan’s progressive moral collapse are parallel demonstrations of what continuous identity performance does to people. Strong dramatic structures can produce thematic content through their architectural commitments.

I think that symmetry is why the film never lets me relax. Every time Costigan and Sullivan are close to each other, my stomach tightens, and I admire how Monahan never lets either man feel safe for more than a scene.

For Writers

A parallel structural commitment can produce thematic content that single-protagonist structures can’t deliver. The Departed’s two infiltrators are mirror images whose specific damage shows the costs of sustained identity performance. The lesson is that strong dramatic structures often involve characters whose situations rhyme. Build the parallels. Let the rhymes do the thematic work. The reader will absorb the argument through the structural correspondence.

The Infernal Affairs Adaptation

Andrew Lau and Alan Mak’s Infernal Affairs (2002) is the Hong Kong source material. The original film was a considerable commercial and critical success in Asian cinema and produced two sequels. William Monahan’s adaptation transposes the Hong Kong police-versus-triad setting to Boston police-versus-Irish-American organized crime. The adaptation preserves the dual-infiltration structure while considerably expanding the supporting cast, the runtime (Infernal Affairs runs one hundred and one minutes; The Departed runs one hundred and fifty-one minutes), and the character development.

The adaptation has been the source of ongoing critical conversation about cross-cultural film adaptation.

Some critics have argued that the additional runtime and character development represent legitimate creative expansion of the source material. Others have argued that the original’s specific structural economy was the source of its dramatic power and that The Departed’s expansion dilutes the impact. Both readings have merit. The films are different works addressing similar premises. Both should be watched. Strong source material can support multiple adaptations operating in different tones without diminishing either work.

I lean toward the longer film. The extra fifty minutes give Costigan’s exhaustion room to build until I can feel it in my own shoulders, and I’d miss the expanded supporting cast, Wahlberg’s Dignam most of all.

For Writers

Cross-cultural adaptation can produce work that works differently from the source without diminishing either version. The Departed and Infernal Affairs are different films addressing similar premises. The lesson is that adaptation is interpretation. The cultural translation involves choices about which elements transfer and which require local reinvention. Each adaptive choice produces specific effects. The work that emerges from the process is its own thing. Pretending that adaptation is reproduction misses what adaptation does.

The Nicholson Performance

Jack Nicholson plays Frank Costello with sustained committed eccentricity that’s divided audiences across two decades. The character is loosely based on the real Boston crime figure James “Whitey” Bulger. The performance refuses naturalistic restraint in favor of theatrical menace.

Nicholson improvises major portions of his dialogue. The character’s specific quirks (the rats, the cocaine, the elaborate suits, the prosthetic finger) all read as Nicholson’s specific contributions instead of as Monahan’s script.

The performance has been the source of significant disagreement. Some critics read the work as one of Nicholson’s most accomplished late-career performances. Others read the work as Nicholson’s mannerisms overwhelming Monahan’s intended character. The film around the performance accommodates either reading. The Costello character functions structurally whether the audience reads Nicholson’s choices as character commitment or as star excess. Strong star performances can sustain films even when the individual performance choices aren’t universally endorsed.

The audience that engages with Nicholson’s specific approach gets one kind of experience. The audience that resists gets another. Both audiences can support the film.

I land somewhere in the middle. Nicholson is a hoot in his early scenes, and then the rats and the prosthetic finger and the improvised riffs start to feel like a man entertaining himself on company time. Those scenes lose me for a few minutes at a stretch, and they’re most of why this sits at a 9.

For Writers

A strong performer can produce work that divides audiences and still sustains a film through structural function instead of through universal endorsement. Jack Nicholson’s Frank Costello works whether the audience embraces or resists his choices. The lesson is that not every creative decision requires unanimous approval. Some choices polarize. The polarization can support the work as long as the structural function is performed. Pick choices that produce strong responses. Mixed strong responses are better than uniform weak ones.

Craft Note

The elevator sequence is the film’s most economical structural payoff. Billy Costigan has identified Colin Sullivan as Frank Costello’s mole inside the Massachusetts State Police. He arranges to meet Sullivan in an elevator at police headquarters to arrest him. Sullivan has anticipated the meeting. Multiple other Costello-aligned officers are in the elevator. The sequence stages the simultaneous resolution of multiple plot threads in approximately ninety seconds. Costigan is shot. Sullivan survives. The shootout that follows resolves several additional characters’ arcs.

A single sustained sequence can perform the work of multiple separate scenes when the staging commits to the spatial logic of the location. The elevator is the entire film’s plot collapsing into one location at one moment. The sequence has been imitated repeatedly. The original works because every preceding moment has been preparing the convergence.

Is The Departed as good as people say?

9/10. The dual-infiltration setup, the Boston atmosphere and that elevator sequence, which knocks the wind out of me with how fast it’s over, make this the most purely entertaining film Scorsese made in the 2000s. I’d dock the point for a crowded second act and for the stretches where Nicholson plays to the back row. Watch Infernal Affairs (2002) for the lean Hong Kong original, then watch this for the bigger, rowdier American version.

Frequently Asked Questions

Was this Scorsese’s first Oscar?
Yes for Best Director. The Departed was his first Academy Award after multiple nominations across previous decades. The film also won Best Picture, Scorsese’s first in that category.
Is The Departed based on a Hong Kong film?
Yes. Andrew Lau and Alan Mak’s Infernal Affairs (2002). The original film produced two sequels. The Departed adapts the first film only.
How accurate is the Boston organized crime material?
Loosely. Frank Costello is partly based on James “Whitey” Bulger, the real Boston crime figure. Specific events are fictional. The general culture of South Boston organized crime in the period is dramatized with reasonable specificity.
How is Vera Farmiga?
Strong. The Madolyn Madden character requires the actress to play simultaneous emotional connections with both protagonists. Farmiga sustains the dual romantic arc despite the structural difficulty.
Who is William Monahan?
American screenwriter. Kingdom of Heaven (2005), The Departed (2006), Body of Lies (2008). The Departed remains his most-recognized credit.
Why did Scorsese finally win for this instead of for earlier films?
The Academy’s specific recognition patterns have been the subject of ongoing critical analysis. The Departed is widely considered less ambitious than several earlier Scorsese films (Goodfellas, Raging Bull, Taxi Driver) that didn’t win the same categories.
Is The Departed worth watching?
Yes. The Departed is one of the major American crime films of the 2000s. Watch Infernal Affairs for comparison.

About the Author
Richard Lowe, professional ghostwriter

Richard Lowe is a professional ghostwriter and author with 113+ books authored and 54+ ghostwritten. Before writing full time he spent 33 years in enterprise technology, including 20 years as Director of Computer Operations and Technical Services at Trader Joe's. He writes nonfiction, fiction and memoir, and works with executives and experts on books that build authority.

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Disclaimer

The views and opinions expressed in this blog post are solely those of Richard Lowe and are based on personal experience and research. This content is for informational purposes only and should not be construed as professional legal, financial, accounting, or business advice. Always consult with qualified professionals before making important business or legal decisions. Richard Lowe is not a lawyer, accountant, or licensed professional advisor, and this content does not establish any professional relationship.