50 Fun Facts About The Departed

The Departed was only the second remake of Scorsese's career; which thriller was the first?

Cape Fear: he remade the 1962 thriller in 1991, and fifteen years later his second remake finally won him the directing Oscar he had lost five times.

The Departed is a remake of which 2002 Hong Kong film?

Infernal Affairs was such a hit that rival Hollywood studios spent a week bidding for the remake rights early in 2003; Warner Bros. won.

Who plays the Irish mob boss Frank Costello?

Jack Nicholson, in his first film for Scorsese, improvised so freely that co-stars said they often didn't know what would happen next in a scene.

Which real-life gangster is Frank Costello loosely based on?

Whitey Bulger was still on the run when the film came out: he fled Boston ahead of an indictment in 1995 and was caught in Santa Monica, California, only in 2011.

Which actor plays the undercover trooper Billy Costigan?

Leonardo DiCaprio was making his third film in a row for Scorsese, and prepared for this one with a retired officer who had spent years working undercover.

Which Boston-raised actor plays Colin Sullivan, Costello's mole in the police?

Matt Damon grew up in the Boston area and described the job as 'the dream of all dreams': Scorsese directing a film about his home city, which he called a really easy yes.

Which star was slated to play Colin Sullivan in The Departed but chose to produce it instead?

Brad Pitt decided he was too old and that the cops should be younger men just starting out; he had spent two and a half years developing the remake as a producer.

Which Scorsese regular turned down the part of Captain Queenan in The Departed?

Robert De Niro was busy directing The Good Shepherd, which is the usual explanation; Scorsese's own version is that his old collaborator simply wasn't interested.

Who plays the foul-mouthed sergeant who works under Queenan in The Departed?

Mark Wahlberg, born in Boston's Dorchester neighbourhood, took the only acting Oscar nomination in a cast full of bigger names.

Who plays Captain Queenan?

Martin Sheen's captain is one of only two officers who know Costigan is a policeman, so his death leaves the undercover man with almost no one to vouch for him.

Which British actor plays Mr. French, Costello's enforcer?

Ray Winstone, a Londoner playing a Boston gangster, was singled out by Roger Ebert, who wrote that he 'invests every line with the authority of God dictating to Moses'.

Who plays Dr. Madolyn Madden, the police psychiatrist involved with both Sullivan and Costigan?

Vera Farmiga's psychiatrist merges two women from the Hong Kong original into one, the change that film's star said he liked least about the remake.

Which actor plays Captain Ellerby, Sullivan's boss?

Alec Baldwin's Ellerby runs the Special Investigation Unit and picks Sullivan to hunt for the leak, unknowingly asking the informer to find himself.

Which law-enforcement agency employs both Costigan and his rival mole?

Massachusetts State Police: Costello steers Sullivan into its academy after grooming him since boyhood, while its commanders pull Costigan out of the same academy to go undercover.

What does Costigan do to establish his cover before joining Costello's crew?

Serves a prison term: his handlers have him plead guilty to assault and battery and do real jail time, so that nobody in Costello's world can doubt the failed trainee's record.

What is Costello selling to Chinese mobsters in the sting that Sullivan sabotages?

Stolen microprocessors: Queenan calls them military technology, and the sting fails because Sullivan, watching alongside the police, warns Costello about the cameras by text message.

What secret about Costello does Costigan uncover and share with Queenan?

He is a protected FBI informant, and it costs him his life: when the wounded Costello admits it, Sullivan shoots the man who planted him in the police.

Which of Costello's henchmen tells Costigan he knows he is the mole, then dies?

Timothy Delahunt had given him the wrong address by mistake; dying, he tells Costigan he turned up at the right one, and takes the secret no further.

Which actor plays Trooper Brown, Costigan's police academy classmate?

Anthony Anderson's trooper walks in on his old classmate holding a fellow officer at gunpoint and has to decide, with seconds to spare, which of them to believe.

What does Costigan spot on Sullivan's desk that reveals Sullivan is the mole?

Costello's envelope: Costigan had written 'Citizens' on it himself, correcting a gang member's spelling, so he knew it the moment he saw it on the desk.

Where does Costigan arrest Sullivan near the end of The Departed?

On the roof from which Queenan fell: Costigan picks the spot himself, but with his captain dead there is almost nobody left who can confirm that he is the policeman and Sullivan the criminal.

Who shoots Costigan in the elevator?

Trooper Barrigan, a classmate of Sullivan's since the academy, turns out to be a second Costello man inside the force; Sullivan shoots him moments later and pins everything on him.

Who kills Sullivan in the final scene?

Dignam had been suspended after coming to blows with Sullivan over Queenan's death; he is waiting inside the apartment, fires once and walks out.

What animal appears on Sullivan's window ledge in the final shot?

A rat: the script simply had one come out to eat the croissants, and Scorsese kept it, he said, not as a literal image but as the film-makers' comment on a story full of informers.

Which letter does Scorsese use as a visual motif to foreshadow death throughout The Departed?

X: the trick is borrowed from Howard Hawks's 1932 Scarface, and it turns up in taped windows, girders and floor patterns shortly before characters die.

Which Boston landmark fills the view from Sullivan's apartment and the backdrop of The Departed's final shot?

The State House: its gold dome is the view Sullivan stretches himself to rent, and Scorsese called the closing shot of it a throwback to old gangster films such as Scarface.

Which opera provides Costello's phone ringtone?

Lucia di Lammermoor: Costello also listens to its famous Act 2 sextet, sung in the opera as a marriage contract is signed and a betrayed lover bursts in.

Who composed the guitar-driven score for The Departed?

Howard Shore, famous for the orchestral Lord of the Rings scores, wrote this one for guitars instead; Scorsese called it 'a very dangerous and lethal tango'.

Which Pink Floyd song, sung by Roger Waters with Van Morrison and The Band, opens The Departed's soundtrack album?

Comfortably Numb: this version comes from The Wall concert staged in Berlin in 1990 to mark the fall of the Berlin Wall, with Van Morrison singing David Gilmour's part.

Which Boston Celtic-punk band's song 'I'm Shipping Up to Boston' features in The Departed?

Dropkick Murphys set music to a Woody Guthrie lyric about a sailor hunting for his wooden leg, and the film's use of it turned the song into the band's calling card.

The Departed won which of these Oscars?

Best Picture, with directing, adapted screenplay and film editing; the room gave Scorsese a standing ovation for a first Oscar greeted as long overdue, 26 years after his first nomination.

Who won the Oscar for editing The Departed?

Thelma Schoonmaker has cut every Scorsese film since Raging Bull, and all three of her editing Oscars are for his pictures: Raging Bull, The Aviator and this one.

Who wrote the Oscar-winning adapted screenplay for The Departed?

William Monahan, a Boston native hired before any director was attached, moved the Hong Kong story to the Irish-American city he grew up in; it was only his second produced script.

Who beat The Departed's only acting nominee to the Best Supporting Actor Oscar?

Alan Arkin won as the foul-mouthed grandfather of Little Miss Sunshine, so one profane supporting turn lost to another.

Before The Departed won Scorsese his Oscar, Raging Bull lost him the directing prize to which actor turned director?

Robert Redford won for Ordinary People in 1981, and ten years later Goodfellas lost to another actor making his first film as a director, Kevin Costner; The Departed was Scorsese's sixth nomination.

In The Departed's opening scenes, where does Costello first take notice of the boy Colin Sullivan?

At a corner lunch counter, where Costello is collecting his cut: he fills the boy's bag with bread, milk and comic books, and the grooming of a future police spy begins.

Why were many of The Departed's interior scenes shot in New York rather than Boston?

Tax incentives for filmmakers: New York had them and Massachusetts did not, to the dismay of one Boston-raised star; the state brought in its own soon afterwards and the work moved north.

Which actor later played the real gangster behind Frank Costello in the 2015 film Black Mass?

Johnny Depp took the part in a biopic made four years after the FBI finally caught the fugitive, whose story had already fed The Departed while he was still on the run.

Which Simpsons episode parodies The Departed?

The Debarted: a new boy becomes Bart's partner in pranks while secretly reporting on him to Principal Skinner, the film's mole plot moved to Springfield Elementary.

What happened to the planned sequel to The Departed?

It was shelved: the screenwriter had an idea that brought back characters who die in the film, but it would have been very expensive and Scorsese did not want to make a sequel.

Who directed the Hong Kong film that The Departed remakes?

Andrew Lau and Alan Mak: Mak also co-wrote the original script with Felix Chong, which is why both writers' names appear in The Departed's own credits.

Which two stars play the undercover cop and the triad mole in the Hong Kong original?

Andy Lau and Tony Leung did not stop at acting: the two also sang the film's theme song as a duet, and it won Best Original Film Song at the Hong Kong Film Awards.

The Hong Kong original's star said The Departed felt like what?

Three films combined: he found it too long, as if Hollywood had rolled the whole trilogy into one, yet still gave it eight out of ten and called it worth seeing.

Which Rolling Stones song did Scorsese use in The Departed, as he had in Goodfellas and Casino?

Gimme Shelter turns up so often in his films that when Scorsese shot the Rolling Stones in concert for Shine a Light, Mick Jagger joked it was the only one without the song.

Which corrupt FBI agent is also cited as a real-life basis for The Departed?

John Connolly had known the gangster behind the film's mob boss since boyhood in the same neighbourhood, tipped him off before his indictment, and ended up in prison himself.

Which real Boston crime organization is The Departed loosely based on?

The Winter Hill Gang was named for a Somerville neighbourhood, not for its boss Howie Winter; when he was jailed for fixing horse races, the man who took over became the model for Frank Costello.

Which Friends star was named as a producer when Warner Bros. bought the remake rights behind The Departed?

Jennifer Aniston was a partner in the company that helped Warner Bros. pay $1.75 million for the rights in 2003, but she had settled her share of it by the time the film won its Oscars, and her name is not on it.

Coppola, Lucas and which other old friend handed Scorsese his Oscar for The Departed?

Steven Spielberg stood with Coppola and Lucas to present the prize, and Scorsese's first words to the standing ovation were a joke asking his old friends to check the result again.

In which Boston neighbourhood is The Departed mainly set?

South Boston, the Irish-American stronghold known as Southie, is Costello's territory on screen, though many of the rooms the characters sit in were built or found in New York.

Which single award did The Departed win at the 64th Golden Globes from six nominations?

Best Director was its only win: the drama prize went to Babel, and two of its cast lost the supporting-actor category they were both nominated in.