Director Martin Scorsese's crime thriller The Departed marked the 20th anniversary of its theatrical release on Oct. 6, 2006, standing as the only film in his career to earn him an Academy Award for Best Director.
The American and Hong Kong co-production runs two hours and 31 minutes. Its star-studded cast features Jack Nicholson, Leonardo DiCaprio, Matt Damon, Vera Farmiga, Martin Sheen, Mark Wahlberg, Alec Baldwin, and Ray Winstone.
When the movie arrived in international theaters two decades ago, the global box office was dominated by Harry Potter, Pirates of the Caribbean, and Star Wars. Marvel's film division was only beginning to set up its own production studio, as the original Iron Man would not arrive until 2008, leaving Batman Begins in 2005 as the only notable comic book film of the era.
Hollywood escapism of that period served as a dress rehearsal compared to modern cinema. Against that backdrop, Scorsese released The Departed as his 20th feature film and his first to receive an Academy Award.
Origins and adaptation of Infernal Affairs
The plot was adapted from the 2002 Hong Kong crime film Infernal Affairs. Scorsese's selection as director was logical and fitting, as Hong Kong gangster cinema drew inspiration from his 1973 film Mean Streets, and Scorsese had frequently expressed his affection for Asian films.
Producer Brad Grey and actor Brad Pitt purchased the rights to remake the film in 2003, one year after Infernal Affairs debuted. Pitt originally intended to play a leading role before script duties were given to novice screenwriter William Monahan.
Monahan had previously written the unproduced screenplay Tripoli, about the Barbary War, as well as Kingdom of Heaven, which was then in production under director Ridley Scott and only achieved wide recognition following its director's cut release.
Setting the Boston mob story
Monahan chose to move the setting to his home state of Massachusetts. He placed the story in Boston, the American center of Irish organized crime.
The story follows two State Police Academy graduates named Colin Sullivan, played by Matt Damon, and Billy Costigan, played by Leonardo DiCaprio.
Sullivan builds a successful police career while providing confidential intelligence to mafia boss Frank Costello, played by Jack Nicholson. Costello had supported Sullivan since childhood by giving him groceries and comic books.
Costigan receives a stern proposal from Captain Queenan, played by Martin Sheen, and his abrasive colleague Sergeant Dignam, played by Mark Wahlberg. They order him to get into a fight, serve four months in prison, and infiltrate Costello's criminal syndicate.
The dual mole operation is linked by police psychologist Madolyn Madden, played by Vera Farmiga, who develops romantic relationships with both men.
Casting decisions and real-life inspirations
Scorsese sought an actress with vintage charm for the role of Madolyn, offering the part to Kate Winslet, Emily Blunt, and Hilary Swank before casting Farmiga. The character did not exist in the Hong Kong original and served as a central key to Scorsese's vision for the script.
Scorsese deliberately chose not to watch Infernal Affairs. He noted that the story reminded him of his favorite film noir, White Heat, which starred James Cagney as a mob boss and Edmond O'Brien as an undercover agent.
Jack Nicholson brought classic Hollywood presence to the set, though he was not the director's initial choice. Scorsese originally envisioned Al Pacino for the role of Costello, though their first collaboration was delayed until The Irishman years later.
Nicholson, who is of mixed Irish and Italian descent, previously starred as Jimmy Hoffa in Danny DeVito's 1992 film Hoffa. Pacino later portrayed the same historic figure in The Irishman.
By 2006, Nicholson had spent several years starring in comedy projects like As Good as It Gets, Mars Attacks!, and Something's Gotta Give. After consideration, he agreed to portray Costello's sinister nature on screen.
Real-life figures inspired several characters. Costello was modeled on Boston mobster James "Whitey" Bulger, who had recently been sent to prison. Damon prepared for Sullivan by interning at a Boston police station for two months and studying former FBI agent John Connolly Jr., who was convicted in 2002 for mob ties.
Wahlberg gave Dignam exaggerated traits based on police officers he argued with during his teenage career as a rapper. The explicit dialogue resulted in the word fuck being spoken 237 times in the film, alongside uncounted profanities.
Production budget and cast overlaps
Scorsese moved filming to his familiar hometown of New York City to double for Boston, making production more comfortable and affordable. Though it was not Scorsese's costliest project due to earlier historical films like The Aviator and Gangs of New York, the budget expanded to $90 million.
The financial investment yielded strong returns for distributor Warner Bros., with the film earning $291.5 million at the box office.
Star-studded casting added to production costs. Scorsese wanted Robert De Niro to play Queenan's supervisor, but De Niro was busy directing his Cold War CIA mole drama The Good Shepherd. DiCaprio turned down the lead role in The Good Shepherd to star in The Departed, leading Damon to take the part in De Niro's film instead.
Alec Baldwin worked on both projects, taking the minor role of Special Investigations chief Ellerby in Scorsese's film. Sheen expressed happiness at playing Queenan after wanting to work with Scorsese for years, despite his role being limited to several dialogue scenes.
Themes style and soundtrack choices
Scorsese replaced the moral anguish of the Hong Kong police officers with an auteur Catholic parable exploring evil, sin, and retribution, photographed by cinematographer Michael Ballhaus. The title itself carries a double meaning referring to the dead.
Costigan stands as the only righteous figure, portrayed by DiCaprio with intense suffering reminiscent of a Dostoevsky character without the axe or old woman. Damon portrays Sullivan as a servant of two masters whose identity crisis is reflected in temporary romantic issues.
Nicholson's Costello dominates as an evil spirit rather than a standard mob boss. Scorsese trusted Nicholson's creative judgment, allowing him to rewrite sections of his role and improvise during filming.
Nicholson introduced two notable unscripted moments, quoting John Lennon while holding a severed hand and waving a large rubber dildo at Sullivan inside an adult theater.
Thelma Schoonmaker, who has edited Scorsese's films since Raging Bull, gave the movie energetic pacing. The timeline remains ambiguous, appearing to span several months while Costigan states he has spent years undercover.
Music provides emotional framing. During a press conference for the Rolling Stones concert film Shine a Light, singer Mick Jagger joked that The Departed was a rare Scorsese project without the song Gimme Shelter, though the track appears near the start of the movie. Later scenes feature Comfortably Numb performed by Roger Waters and Van Morrison.
One theatrical scene emphasizes Costello's villainy by showing Nicholson tossing a handful of white powder toward the camera lens.
Academy Awards recognition and legacy
Looking back from today, The Departed represents Nicholson's last major film role before entering an informal retirement. Now approaching age 90 with three Oscars, he rarely leaves home except to attend Los Angeles Lakers basketball games.
The film earned four Academy Awards, winning Best Picture, Best Adapted Screenplay, Best Film Editing, and Best Director.
First nominated in 1981 for Raging Bull, Scorsese admitted on stage that he was surprised by the win and asked presenters Francis Ford Coppola, George Lucas, and Steven Spielberg to double-check the envelope.
Scorsese dedicated his first Oscar to supporters who had wished him victory over the years, including passersby on New York streets. His view on awards was later illustrated when he fell asleep during Eminem's performance at the 2020 Oscars, where The Irishman was nominated.
While film fans debate whether Scorsese deserved the Oscar earlier for Taxi Driver, Goodfellas, or Casino, The Departed arrived five years after Sept. 11, when American audiences were ready to exit a post-traumatic state through realistic cinema.
Scorsese valued the opportunity to direct a contemporary story. Since completing The Departed, he has returned to modern settings only through documentary films.
