The Departed Trivia
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50 free The Departed trivia questions with answers — entertainment quiz, new questions added Aug 2026.
This The Departed trivia quiz covers Martin Scorsese's 2006 Best Picture winner from every angle. It starts with the plot: Billy Costigan undercover in Frank Costello's crew, Colin Sullivan as the mole inside the Massachusetts State Police, Queenan's fall, the elevator, and the rat on the window ledge. Then it moves to the cast (who was originally slated to play Sullivan, why Robert De Niro turned down Queenan, who suggested Matt Damon), the real-life Whitey Bulger connection, the X motif borrowed from the 1932 Scarface, the soundtrack, and the Oscar night that finally gave Scorsese his statuette. There is also a short round on Infernal Affairs, the 2002 Hong Kong film the story comes from, and what its own directors and stars thought of the remake. Questions run from easy (who plays Costello) to expert (which opera is Costello's ringtone). Every answer was checked against encyclopaedia entries before publishing.
30 of 50 questions with answers and explanations. Play the quiz
Q 01The Departed was only the second remake of Scorsese's career; which thriller was the first?
Cape Fear
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.
Q 02The Departed is a remake of which 2002 Hong Kong film?
Infernal Affairs
Infernal Affairs was such a hit that rival Hollywood studios spent a week bidding for the remake rights early in 2003; Warner Bros. won.
Q 03Who plays the Irish mob boss Frank Costello?
Jack Nicholson
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.
Q 04Which real-life gangster is Frank Costello loosely based on?
Whitey Bulger
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.
Q 05Which actor plays the undercover trooper Billy Costigan?
Leonardo DiCaprio
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.
Q 06Which Boston-raised actor plays Colin Sullivan, Costello's mole in the police?
Matt Damon
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.
Q 07Which star was slated to play Colin Sullivan in The Departed but chose to produce it instead?
Brad Pitt
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.
Q 08Which Scorsese regular turned down the part of Captain Queenan in The Departed?
Robert De Niro
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.
Q 09Who plays the foul-mouthed sergeant who works under Queenan in The Departed?
Mark Wahlberg
Mark Wahlberg, born in Boston's Dorchester neighbourhood, took the only acting Oscar nomination in a cast full of bigger names.
Q 10Who plays Captain Queenan?
Martin Sheen
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.
Q 11Which British actor plays Mr. French, Costello's enforcer?
Ray Winstone
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'.
Q 12Who plays Dr. Madolyn Madden, the police psychiatrist involved with both Sullivan and Costigan?
Vera Farmiga
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.
Q 13Which actor plays Captain Ellerby, Sullivan's boss?
Alec Baldwin
Alec Baldwin's Ellerby runs the Special Investigation Unit and picks Sullivan to hunt for the leak, unknowingly asking the informer to find himself.
Q 21Where does Costigan arrest Sullivan near the end of The Departed?
On the roof from which Queenan fell
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.
Q 22Who shoots Costigan in the elevator?
Trooper Barrigan
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.
Q 23Who kills Sullivan in the final scene?
Dignam
Q 14Which law-enforcement agency employs both Costigan and his rival mole?
Massachusetts State Police
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.
Q 15What does Costigan do to establish his cover before joining Costello's crew?
Serves a prison term
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.
Q 16What is Costello selling to Chinese mobsters in the sting that Sullivan sabotages?
Stolen microprocessors
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.
Q 17What secret about Costello does Costigan uncover and share with Queenan?
He is a protected FBI informant
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.
Q 18Which of Costello's henchmen tells Costigan he knows he is the mole, then dies?
Timothy Delahunt
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.
Q 19Which actor plays Trooper Brown, Costigan's police academy classmate?
Anthony Anderson
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.
Q 20What does Costigan spot on Sullivan's desk that reveals Sullivan is the mole?
Costello's envelope
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.
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.
Q 24What animal appears on Sullivan's window ledge in the final shot?
A rat
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.
Q 25Which letter does Scorsese use as a visual motif to foreshadow death throughout The Departed?
X
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.
Q 26Which Boston landmark fills the view from Sullivan's apartment and the backdrop of The Departed's final shot?
The State House
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.
Q 27Which opera provides Costello's phone ringtone?
Lucia di Lammermoor
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.
Q 28Who composed the guitar-driven score for The Departed?
Howard Shore
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'.
Q 29Which Pink Floyd song, sung by Roger Waters with Van Morrison and The Band, opens The Departed's soundtrack album?
Comfortably Numb
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.
Q 30Which Boston Celtic-punk band's song 'I'm Shipping Up to Boston' features in The Departed?
Dropkick Murphys
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.