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 01Who directed The Departed?
Martin Scorsese
It finally won him a Best Director Oscar after five previous losses.
Q 02The Departed is a remake of which 2002 Hong Kong film?
Infernal Affairs
Warner Bros. and producers Brad Grey and Brad Pitt bought the remake rights for $1.75 million.
Q 03Who plays the Irish mob boss Frank Costello?
Jack Nicholson
He wanted the film to have 'something a little more' than the usual gangster picture, which led to the Whitey Bulger idea.
Q 04Which real Boston gangster is Frank Costello loosely based on?
Whitey Bulger
Like Costello, Bulger operated with wide latitude as a protected FBI informant.
Q 05Which actor plays the undercover trooper Billy Costigan?
Leonardo DiCaprio
He was nominated for a Golden Globe for the role.
Q 06Which Boston-raised actor plays Colin Sullivan, Costello's mole in the police?
Matt Damon
Scorsese's associate Kenneth Lonergan suggested him for the part.
Q 07Which star was originally slated to play Sullivan but decided to produce the film instead?
Brad Pitt
He said a younger actor should play the part.
Q 08Which actor turned down the role of Captain Queenan in order to direct The Good Shepherd?
Robert De Niro
Martin Sheen took the part instead.
Q 09Who plays the foul-mouthed sergeant who works under Queenan and gets the film's last word?
Mark Wahlberg
He earned the film's only acting Oscar nomination, losing to Alan Arkin.
Q 10Who plays Captain Queenan?
Martin Sheen
He is thrown from a building to his death by Costello's men.
Q 11Which British actor plays Costello's enforcer 'Frenchie' French?
Ray Winstone
Winstone's character is Arnold French, called Mr. French throughout.
Q 12Who plays Dr. Madolyn Madden, the police psychiatrist involved with both Sullivan and Costigan?
Vera Farmiga
The remake merged the original film's two female characters into one, which Andy Lau thought weaker.
Q 13Which actor plays Captain Ellerby, Sullivan's boss?
Alec Baldwin
Ray Liotta was also approached for a role but was committed elsewhere.
Q 21Where does Costigan arrest Sullivan near the end of the film?
On the roof from which Queenan fell
A fellow trooper arrives while he holds Sullivan at gunpoint and hears him claim to have evidence.
Q 22Who shoots Costigan in the elevator?
Trooper Barrigan
Barrigan reveals he is another of Costello's spies; Sullivan then shoots Barrigan and frames him as the only mole.
Q 23Who kills Sullivan in the final scene?
Dignam
He had been suspended after an altercation with Sullivan following Queenan's murder.
Q 14Which law-enforcement agency employs both Costigan and his rival mole?
Massachusetts State Police
Sullivan joins its Special Investigation Unit; Costigan is recruited by Queenan and Dignam straight from the academy.
Q 15What does Costigan do to establish his cover before joining Costello's crew?
Serves a prison term
He then commits several crimes to draw Costello's attention.
Q 16What is Costello selling to Chinese mobsters in the sting that Sullivan sabotages?
Stolen microprocessors
Both sides realise afterwards that they have a mole.
Q 17What secret about Costello does Costigan uncover and share with Queenan?
He is a protected FBI informant
Sullivan later confirms it from Queenan's files, and Costello admits it before Sullivan shoots him.
Q 18Which of Costello's henchmen tells Costigan he knows he is the mole, then dies?
Timothy Delahunt
A news report later identifies him as an undercover Boston police officer, which Costello suspects is a ruse.
Q 19Which actor plays Trooper Brown, Costigan's police academy classmate?
Anthony Anderson
Kevin Corrigan plays Costigan's cousin Sean; David O'Hara is Fitzy.
Q 20What does Costigan spot on Sullivan's desk that reveals Sullivan is the mole?
Costello's envelope
He had earlier watched Costello hand the envelope to a man he could not identify.
Q 24What animal appears on Sullivan's window ledge in the final shot?
A rat
Scorsese said it symbolises the 'quest for the rat' and the distrust running through the film, not to be taken literally.
Q 25Which letter does Scorsese use as a visual motif to foreshadow death throughout the film?
X
The device is borrowed from Howard Hawks's 1932 Scarface; it appears behind Costigan's head in the elevator.
Q 26The funeral scene, where Madden walks past Sullivan without looking, quotes the ending of which classic film?
The Third Man
Scorsese also cited that film's zither score as an inspiration for the guitar-based music.
Q 27Which opera provides Costello's phone ringtone?
Lucia di Lammermoor
He is also seen listening to the famous sextet from Act 2 of Donizetti's opera.
Q 28Who composed the guitar-driven score?
Howard Shore
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 album?
Comfortably Numb
The Dropkick Murphys' 'I'm Shipping Up to Boston' is on the same album.
Q 30Which Boston Celtic-punk band's song 'I'm Shipping Up to Boston' features in the film?
Dropkick Murphys
The soundtrack also includes the Rolling Stones' 'Let It Loose' and Badfinger's 'Baby Blue'.