When the film won the Oscar for Best Picture, Martin Scorsese said that he was surprised the film had won. Scorsese said that because the film is such a tough, nasty, and violent film, he never thought about the idea of awards while he was filming it.
Mark Wahlberg based his performance on the police officers who'd arrested him about two dozen times in his youth, and the reactions of his parents who had to come bail him out with their grocery money.
Leonardo DiCaprio described his character as being in a "constant, 24-hour panic attack."
Martin Scorsese really wanted Al Pacino for the role of Costello, because he never worked with Pacino before, but he turned it down. Jack Nicholson was Scorsese's second choice. Pacino would later go onto appear in Scorsese's The Irishman.
Leonardo DiCaprio called his one-on-one scene with Jack Nicholson "one of the most memorable moments of my life."
When receiving the top award from the Director's Guild of America for this film, Martin Scorsese said that this "is the first movie I have ever done with a plot."
Martin Scorsese did not realize this was a remake of a Hong Kong movie until after he had agreed to direct it.
A possible reason why Leonardo DiCaprio did not receive an Oscar nomination for his performance in this movie was because Warner Brothers initially did not want to favor DiCaprio over his co-stars, and place him in the leading actor category. The studio favored DiCaprio's leading performance in Blood Diamond (2006),which eventually got him a nomination).DiCaprio refused to campaign against his male co-stars in the supporting actor category, so Warner bought no supporting actor ads for DiCaprio, and he did not receive a nomination.
Originally, Jack Nicholson turned down his role in the movie, but after a meeting with Martin Scorsese, William Monahan, and Leonardo DiCaprio, he was finally convinced to play the role of Frank Costello. The main reason he joined the production, was because he had previously done a few comedies, and wanted to play a villain again, and he considered the character of Costello to be the ultimate incarnation of evil.
Vera Farmiga met with a real LAPD psychiatrist to prepare for her role. The psychiatrist read the script, and told Farmiga that Madolyn did pretty much everything wrong.
Leonardo DiCaprio was cast in the title role in The Good Shepherd (2006), but he dropped out to play Billy Costigan in this movie. Matt Damon then took the role. Robert De Niro turned down the role of Queenan to appear in The Good Shepherd (2006).
Originally, Brad Pitt was cast as Colin Sullivan, but later dropped out to work with Alejandro G. Iñárritu in Babel (2006). He continued to produce the film under his (and his then wife Jennifer Aniston's) production company, Plan B.
This marks the third time that Martin Scorsese has used The Rolling Stones' "Gimme Shelter" in one of his films. It also appeared in Goodfellas (1990) and Casino (1995).
According to Ray Winstone, he and Jack Nicholson did not get along with each other while filming.
Martin Scorsese wanted to shoot the film in Boston, where the story is set. The bulk of the film was shot in New York, partly due to concerns about setting up production and politics, partly because of New York's 15% filmmaking tax credit. They shot in Boston for 3 weeks in June and 3 more in August. After the success of this film, Massachusetts created a 25% tax credit for filmmaking.
Matt Damon decided his character should be impotent to counter Frank's macho personality.
Martin Scorsese put the finishing touches on this film a week before its theatrical release.
Jack Nicholson refused to wear a Boston Red Sox hat during filming, and instead wore his New York Yankees hat.
Mark Wahlberg easily fell back on his native accent. Martin Scorsese joked it was so thick, they'd need subtitles.
After Jack Nicholson joined the cast, his character was re-written, to give him a bigger part.
When Sullivan asks Trooper Barrigan, "Do you have any suits at home, or do you like going to work looking like you're going to invade Poland?", he's referring to the fact that the Nazis modelled their own uniform after Massachusetts State Police uniforms.
Martin Scorsese deliberately chose not to watch Infernal Affairs (2002), until after he'd completed this film.
When Frank (Jack Nicholson) walks off with the angel kids, the yacht in the background is the same yacht Jordan Belfort (Leonardo DiCaprio) owns in The Wolf of Wall Street (2013).
Ray Liotta was the original choice for the role of Dignam, but had to reluctantly decline, due to other commitments.
Screenwriter William Monahan envisioned a sequel to the film, citing that it would've focused on overlooked aspects of the first film, such as political corruption. Monahan had watched the sequels to the original film on which this movie was based, but felt that a potential sequel would've gone in a different direction set by this film. Mark Wahlberg also indicated that Dignam would've been the main character in this film. To date, plans for the sequel haven't materialized.
As research for his character's occupation, Matt Damon worked with a Massachusetts State Police unit out of Boston. He accompanied them on routine patrols, participated in a drug raid, and was taught proper police procedures, like how to pat down a suspect.
At the beginning, when the main characters are in a police academy ballistics lecture, the large flip chart illustrations seen in the background are Warren Commission exhibits of President John F. Kennedy's head wounds, prepared by Medical Illustrator H.A. Rydberg under the direction of Dr. James Humes, the Chief Examiner of Kennedy's autopsy. Texas Governor John Connally was also riding in the car that day, and was also shot. John Connolly is also the name of the F.B.I. Agent who recruited Whitey Bulger as an informant, and ultimately protected him from investigation or prosecution for many years.
Originally, this remake was planned with Brad Pitt as Colin Sullivan, and Tom Cruise as Billy Costigan.
The real mob boss Frank Costello was a contemporary of Lucky Luciano and Meyer Lansky, in New York City.
After completing The Aviator (2004), Martin Scorsese kept Alec Baldwin in mind for future collaboration and ultimately decided to cast him in the role of Ellerby, which was offered to Mel Gibson first, but Gibson was unable to accept the part, because he was starting production on Apocalypto (2006) at the time.
(At around one hour and seventeen minutes) It was Jack Nicholson's idea to film the scene when Frank Costello attends the opera. It was also Nicholson's idea to have one black woman and one white woman in the scene with him.
Colin Sullivan's apartment does not exist. The view of the Massachusetts State House was an effects shot from the roof of Suffolk University, which is the law school where Sullivan says he is taking night classes. Cinematographer Michael Ballhaus evaluated the shot during pre-production.
When Colin has dinner with Madolyn, he states "what Freud said about the Irish is we're the only people impervious to psychoanalysis." According to the FAQ section of the Freud Museum in London, Sigmund Freud , "There is no evidence Freud said the quote. The only documentation seems to be Anthony Burgess, in his introduction to a book of Irish short stories: 'One of Freud's followers split up human psychology into two categories, Irish and non-Irish.'"
According to Martin Scorsese, the film was envisioned as a low-budget production, but the budget increased as more stars became attached.
Warner Brothers bought the remake rights to Infernal Affairs (2002) for 1.75 million dollars in 2003.
Martin Sheen was one of the last actors cast. The reason why he agreed to appear in the film, was because he wanted to work with Martin Scorsese.
Martin Scorsese had originally wanted to cast a known actress, either Kate Winslet, Emily Blunt, Hilary Swank, or Jennifer Aniston, for the part of Madolyn.
One of the reasons Martin Scorsese agreed to direct this movie, was because it reminded him of one his favorite movies White Heat (1949), a film noir starring James Cagney, also partly about an undercover police officer embedded with a charismatic gangster.
On the DVD commentary for Gone Baby Gone (2007), Ben Affleck says that Jay Giannone, who has small roles in both films, was also the Boston accent coach for Leonardo DiCaprio in this movie.
(At around twenty-one minutes) Cousin Sean (Kevin Corrigan) makes a disparaging comment about Puerto Ricans. In real-life, Corrigan is partially of Puerto Rican descent.
Vera Farmiga's character is a composite of two characters from Internal Affairs (2002).
Martin Scorsese joked that he's much more comfortable with gangsters on-set than police. "I was worried that there were cops all around me and they were going to take me in."
This was one of Martin Scorsese's "present day" films, as most of his films take place in the past.
Composer Howard Shore said Martin Scorsese wanted the music score to be a tango, to portray the nature of the deadly game being played by the characters.
Jack Nicholson's mug shot in the movie belongs to his Jack Napier role in Batman (1989), another Warner Bros. production.
The first Best Picture Oscar winner of the twenty-first century that wasn't released on VHS in the United States, and the first to be released on the short-lived HDDVD format. Warner Brothers Home Entertainment had already phased out VHS by 2006, therefore, the film was initially released on DVD, Blu-ray, and HDDVD the following year.
Denis Leary was offered the role of Dignam in this film, but turned it down due to scheduling conflicts with his television show, Rescue Me (2004). He was disappointed, but he did hold Mark Wahlberg's performance in high regard.
This marks the second Martin Scorsese film in which Leonardo DiCaprio plays a young Irish man who infiltrates the ranks of a menacing gangster. The first being Gangs of New York (2002).
(At around thirteen minutes) When Queenan and Dignam are interviewing Costigan, Costigan says "Families are always rising and falling in America." Queenan wants to know who said that, and it turns out to be Nathaniel Hawthorne. Dignam quips, "What's the matter smart ass, don't know any f****n' Shakespeare?" Later (at around one hour and one minute), as Queenan hands the clipboard to Sullivan, it is Queenan who quotes William Shakespeare with "the readiness is all", from Hamlet's "Fall of a sparrow speech," Act V, scene II.
Martin Scorsese said that he made this film to honor crime genre directors, such as Robert Aldrich, Samuel Fuller, and Don Siegel.
Thomas B. Duffy is a retired Massachusetts State Police Major, who worked out of Boston for nearly thirty years, and specialized in organized crime. He was particularly involved in the case against notorious South Boston mob boss James "Whitey" Bulger, on whom Frank Costello is partly based. Duffy appears as the Governor, who delivers a speech to the graduating police cadets. There was an unconfirmed sighting of Bulger, one of the F.B.I.'s Ten Most Wanted, at a theater showing the film by a Deputy Sheriff in San Diego, California. Bulger was captured in Santa Monica, California on June 22, 2011. He'd been living in an apartment complex just a few blocks away from the production offices of GK Films (U.S.), who produced Edge of Darkness (2010), in which Duffy also appeared.
The film cast includes three Oscar winners: Jack Nicholson, Leonardo DiCaprio, and Matt Damon; and three Oscar nominees: Mark Wahlberg, Alec Baldwin, and Vera Farmiga.
There are two phone numbers used in the film. The first is Billy's phone number, which is 617-869-1469 (It appears when Colin Sullivan answers the phone). This is a real Boston number used by Sprint Spectrum. If someone calls it, you will get a generic voicemail box, which is full. The other number is 311-555-2368, which was a phone number used in telephone company publications.
(At around two hours and ten minutes) The CD that Costigan mails to Colin is mailed in the cover for The Rolling Stones' album "Exile on Main St." Earlier in the film (at around thirty-six minutes), when Costello beats Costigan's hand with his own shoe, a song from the album, "Let It Loose", plays over the scene.
Vera Farmiga was nervous about meeting Leonardo DiCaprio and Martin Scorsese. "You expect there to be a certain chasm between you and them, and there wasn't."
(At around one hour and ten minutes) The movie playing in the background at Sullivan's house is Audition (1999).
Martin Scorsese directed Mark Wahlberg to his first Oscar nomination, for his role of Dignam. He was later nominated for The Fighter (2010) for Best Picture.
(At around one hour and fifty-five minutes) The newscaster seen reporting the news story detailing the dumped body by Costello's gang, was a real Boston area newscaster at the time of filming. He reported for Boston's Warner Brothers affiliate station WB56.
RZA was offered Anthony Anderson's role, but turned it down because of scheduling conflicts.
(At around three minutes) The comic book that Frank Costello gives young Colin Sullivan in the beginning of the movie is Issue #11 of the "Wolverine" series, which was published in September 1989.
Martin Sheen and Leonardo DiCaprio rode the Red Line about one hundred times to get enough takes of one sequence.
(At around nineteen minutes) Tom Kemp and Zachary Pauliks appeared in a flashback scene, in which Frank talks to Billy's father, as young Billy looks on. Although the scene was deleted, the actors appear in the picture that Billy gives to his aunt, and the actors are still listed in the closing credits.
Vera Farmiga was one of the only actresses who didn't watch Infernal Affairs (2002), the movie on which this is based. Madolyn is inspired by multiple characters, so Farmiga thought it would be confusing for her.
Martin Scorsese won Best Picture and Best Director Oscars over Clint Eastwood nominated for Letters from Iwo Jima (2006). The two competed two years earlier when Scorsese was nominated in both categories for The Aviator (2004) and Eastwood winning both Oscars for Million Dollar Baby (2004).
Matt Damon and Andy Lau (the mole in the original Chinese film) appeared in The Great Wall (2016).
(At around one hour and seventeen minutes) Frank Costello attended the Gaetano Donizetti opera Lucia di Lammermoor. This is a musical homage to Scarface (1932), as Paul Muni's character would often whistle the sextet from this opera, whenever he killed someone.
Frank Costello (Jack Nicholson) was supposed to wear a Red Sox cap in the movie, but refused to. The hatred of Boston sports teams date back to the days of Jack's love affair with the Lakers and the heated rivalry with the Celtics. The Red Sox cap was the signature uniform of James "Whitey" Bulger, but Jack couldn't overcome his disfavor.
1997 was a significant year for the four main actors of this film. Leonardo DiCaprio starred in Titanic (1997), which would go on to become the second highest grossing movie of all time, and win eleven Academy Awards. Matt Damon won an Academy Award for Best Original Screenplay, and got a Best Actor nod for Good Will Hunting (1997). He was beaten for Best Actor by Jack Nicholson for As Good as It Gets (1997). Lastly, Mark Wahlberg stepped into the limelight in the critically acclaimed Boogie Nights (1997).
One of three Best Picture Oscar winners featuring Jack Nicholson. The other two are One Flew Over the Cuckoo's Nest (1975) and Terms of Endearment (1983). Interestingly, it's the only one of the three where he didn't win, nor was nominated for an Oscar.
While shooting on-location in Boston, Massachusetts, Martin Scorsese viewed the film's dailies at Emerson College.
Jack Nicholson says he joined the cast because he was looking for a "nice juicy bad guy to play."
Martin Scorsese wanted Matt Damon to play Sullivan, because he had a "cocky attitude, a bravado."
The first Warner Brothers Best Picture Oscar winner without Morgan Freeman co-starring, since Amadeus (1984). The Best Picture winners in between those from the studio are Driving Miss Daisy (1989), Unforgiven (1992), and Million Dollar Baby (2004).
(At around two hours and five minutes) According to his file, Billy Costigan's birth date is November 7, 1984. Although a second shot of the same screen then labels it as November 7, 1980.
In the scene when Leonardo DiCaprio is at the airport, the little girl that is seen with the pink backpack is Martin Scorsese's daughter Francesca.
(At around two hours and five minutes) When Sullivan looks up Costigan's information on the computer, the computer is a PC, but the graphical interface is actually a Mac.
Peter Mullan was cast in the film, but ended up dropping out. Mullan said "I was not in the right frame of mind. I was exhausted, and I would not have done a good job. It would've been pointless."
This is the first time Martin Scorsese and Jack Nicholson worked together. They first met twenty-eight years earlier on the set of Scorsese's documentary The Last Waltz (1978).
(At around one hour and two minutes) During the exchange with the Chinese gangsters, Sullivan sends a text message to Costello saying that all cell phone calls are being monitored. The number dialed by Sullivan is a real Boston area code (617).
Tyler Perry publicly expressed interest in playing the role that went to Anthony Anderson.
The funeral scene was filmed at Green-Wood Cemetery in Brooklyn, New York. Martin Scorsese also shot Gangs of New York (2002) there.
In Turkey, there is a television series based on this film, named Icerde (2016), which means "Inside".
Matt Damon and Leonardo DiCaprio competed against one another for Best Actor in a Leading Role at the 2015 Academy Awards. DiCaprio ended up being the winner.
To accommodate his schedule, Mark Wahlberg had shot his scenes at the beginning of production.
(At around twenty-eight minutes) When Madolyn meets Colin in the elevator, she gives Colin her business card. The logo of the American Psychological Association is clearly visible on it.
Included among the "1001 Movies You Must See Before You Die", edited by Steven Schneider.
Whenever the song "Sweet Dreams" by Patsy Cline is heard, it is usually in a scene with Jack Nicholson.
Frank wears a Notre Dame Fighting Irish t-shirt. That's where Queenan says his son goes to school.
The classroom scene, police academy graduation scene, and shooting range scene (all at the beginning of the film) were shot near the end of production. Historic Ft. Schuyler on the campus of State University of New York's Maritime College was the backdrop.
Steven Spielberg said that he and Martin Scorsese were going to have a Q and A with each other to talk about the film. However, it never happened.
The "MASS Processor Company's" microprocessor, shown in the movie, is really an ST Microelectronics' ST9F150JDV1QC micro-controller, released in 2003 and intended for applications such as MP3 players, GPS devices, and car radios. It went for around seven dollars at the time it was released (in the movie it is stated they go for one hundred thousand dollars each). The microprocessor has an internal clock frequency of twenty-four Megahertz and one hundred pins, and can hold up to four Megabytes of memory. A typical Intel Core 2 Duo microprocessor, released in 2006 (the same year as The Departed) for use in desktop computers, runs at 1,400 Megahertz or higher frequencies, has 775 pins, and can address up to four thousand Megabytes.
Gerard McSorley was originally slated to play Queenan, but had to drop out of the project.
(At around forty-nine minutes) When Colin (Matt Damon) tells Fitzgibbons (David O'Hara) to call his mother from Trooper Brown's phone, the ringtone on the receiving phone is "Scotland the Brave", one of the tunes played on the bagpipes at the cadets' graduation ceremony.
Warner Brothers and the producers of this movie wanted the running time of the film to be two hours and twenty minutes. The running time ultimately came to be two hours and thirty-one minutes.
Chris Messina met with Martin Scorsese to discuss taking on one of the roles in the film.
Captain Queenan mentions to Billy Costigan that his son attends Notre Dame. Martin Sheen's character from The West Wing (1999), President Josiah Bartlet, went to the same university, and was also a fan of the Boston Celtics.
The picture of the CD that William Costigan (Leonardo Di Caprio) left with Madolyn (Vera Farmiga), is the cover of the 1972 Rolling Stones' album "Exile on Main St."
The only film directed by Martin Scorsese to win Best Picture at the Academy Awards.
If you listen closely in some scenes you can hear the music from 'Rizzoli and Isles' in the background.
The only Best Picture nominee that year to be also nominated for Best Adapted Screenplay, the other four were nominated in the Original Screenplay category.
Matt Damon and Alec Baldwin appeared in The Good Shepherd (2006) and on 30 Rock (2006).