Director: Martin Scorsese
Stars: Leonardo DiCaprio, Matt Damon, Jack Nicholson
Plot: In South Boston, the state police force is waging war on Irish-American organized crime. Young undercover cop Billy Costigan (Leonardo DiCaprio) is assigned to infiltrate the mob syndicate run by gangland chief Frank Costello (Jack Nicholson). While Billy quickly gains Costello's confidence, Colin Sullivan (Matt Damon), a hardened young criminal who has infiltrated the state police as an informer for the syndicate is rising to a position of power in the Special Investigation Unit. Each man becomes deeply consumed by their double lives, gathering information about the plans and counter-plans of the operations they have penetrated. But when it becomes clear to both the mob and the police that there is a mole in their midst, Billy and Colin are suddenly in danger of being caught and exposed to the enemy - and each must race to uncover the identity of the other man in time to save themselves.
It is a remake of the 2002 Hong Kong action movie Infernal Affairs
Jack Nicholson’s character is based on infamous Boston mob boss Whitey Bulger. Before he was captured in 2011, he was second only to Osama bin Laden on the FBI’s Most Wanted List and had a reward of $1 million for his capture.
De Niro, who has made eight films so far with Scorsese, was originally asked to play either mob boss Frank Costello or police Captain Queenan. He declined both in favor of directing his own movie, The Good Shepherd
Whenever anybody is killed onscreen or talks about murder, Scorsese had a hidden “X” positioned somewhere in the frame as an homage to the 1932 version of Scarface (another of Scorsese’s favorite movies) which does the same thing. Examples include shots of Costigan walking through the airport while talking to Sgt. Dignam, Queenan falling to his death (on the building's glass windows as Queenan falls to the ground), and Sullivan in his office discussing the flow of information with Costello (the X is created by the light shining through the window).
Jack Nicholson came up with a bunch of bizarre scene ideas, including throwing cocaine on hookers and the suggestion of wearing a strap-on in the porn theatre. Jack Nicholson was allowed to improvise a lot on camera, and the scene where Billy and Frank are talking was loosely scripted, such as when Frank pulls out the gun.
Originally, this remake was planned with Brad Pitt and Tom Cruise in the lead roles.
Jack Nicholson refused to wear a Boston Red Sox hat during filming and instead chose his New York Yankees hat.
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?", it is actually a remark about the Massachusetts State Trooper uniform; The Nazis modelled their own uniform after that of the trooper.
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.
Martin Scorsese really wanted Al Pacino for the role of Frank Costello because he never worked with Pacino before, but Pacino turned it down. Jack Nicholson was Scorsese's second choice.
The first teaming of Jack Nicholson and Martin Scorsese.
Scorsese wanted to film the movie in Boston, where it takes place, but the studio convinced him to move production to New York City, where they’d receive a 15 percent tax credit. After seeing the success of the film, Massachusetts changed their tax laws, allowing a similar tax discount to help lure more productions to their state.
Scorsese, one of the all-time greatest filmmakers, has won only one Academy Award in his six-decade career -- for directing "The Departed."
After the success of this film there were plans for a sequel starring Mark Whalberg. The original Hong Kong film Infernal affairs had two sequels. But as of 2016 no announcements have been made about it.