Movie Smarts

The Departed Quiz: Keep Your Story Straight

Fifteen chances to prove that all those movie nights paid off.

Published 2026-10-24 Updated 2026-10-24 15 questions

The Departed: Everybody Here Needs a Better Cover Story

A young officer goes undercover inside a crime boss's operation while another man works inside the police for that same boss. Both are trying to identify a spy without revealing the one they see in the mirror. Trust becomes a terrible habit, and even an ordinary phone call can feel dangerous. The pressure keeps building as the two lives move closer to colliding.

Keep your answers straight. There are enough false identities already.

1. Who directed The Departed?
- Michael Mann
- Martin Scorsese
- David Fincher
- Brian De Palma
Scorsese marks the characters who are about to die with an X somewhere in the frame, a trick borrowed from Howard Hawks's 1932 Scarface. Brian De Palma, among the distractors, directed the 1983 remake of that film with Al Pacino.
2. Who plays undercover officer Billy Costigan?
- Leonardo DiCaprio
- Mark Wahlberg
- Edward Norton
- Matt Damon
Costigan's family ties to the Southie underworld make him useful, so Queenan and Dignam wipe his record and have him do real jail time on an assault charge to build the cover. It was DiCaprio's third film in a row with Scorsese.
3. Who plays police mole Colin Sullivan?
- Leonardo DiCaprio
- Ben Affleck
- Matt Damon
- Casey Affleck
Costello put Sullivan through school and steered him toward the state police, so he has a man inside before Sullivan has even graduated. Damon and DiCaprio had never worked together before, and the film keeps the two of them apart until the very end.
4. Who plays crime boss Frank Costello?
- Robert De Niro
- Jack Nicholson
- Harvey Keitel
- Al Pacino
Nicholson had never worked with Scorsese before and improvised much of the part; producing a pistol at the table during his talk with Costigan was his idea, and DiCaprio's alarm is genuine. Costello is loosely drawn from Whitey Bulger, the South Boston boss.
5. Which city is the main setting?
- Chicago
- New York
- Philadelphia
- Boston
South Boston specifically, Costello's home turf, though much of the shoot was done in New York with Boston landmarks dropped into the backgrounds. Damon, from Cambridge, and Wahlberg, from Dorchester, are the ones with the real accents.
6. Which Hong Kong film supplied the main story?
- Infernal Affairs
- Election
- A Better Tomorrow
- Hard Boiled
Andrew Lau and Alan Mak's 2002 thriller, with Tony Leung as the undercover cop and Andy Lau as the mole, had a prequel and a sequel before Hollywood got to it. Election is Johnnie To's triad film; A Better Tomorrow and Hard Boiled are John Woo's.
7. What does Costigan order at the bar, earning a joke at his expense?
- A Guinness
- A cranberry juice
- A whiskey
- A club soda
A regular informs him it is a natural diuretic and asks whether he has his period, and Billy answers by breaking a glass over the man's head. Mr French, Costello's enforcer, played by Ray Winstone, breaks it up, and the brawl gets Billy noticed.
8. Which captain runs the Special Investigations Unit that Sullivan joins?
- Queenan
- Dignam
- Ellerby
- Brown
Ellerby, played by Alec Baldwin, later hands Sullivan the job of finding Costello's man inside the department, which is to say himself. Queenan, Martin Sheen's captain, runs the undercover operation with Dignam, Mark Wahlberg's permanently furious sergeant.
9. Which Rolling Stones song plays under Costello's opening monologue?
- Sympathy for the Devil
- Gimme Shelter
- Paint It Black
- Monkey Man
Scorsese had already used it in Goodfellas and Casino; here it runs under Costello's speech about wanting his environment to be a product of him rather than the other way around. Monkey Man, among the distractors, is another Goodfellas track.
10. Which police organization employs Sullivan and Costigan?
- Massachusetts State Police
- Boston Transit Police
- The FBI
- New York State Police
Both men come through the same academy class, and the film is about troopers rather than Boston city cops. Queenan's undercover unit and Ellerby's Special Investigations Unit share a building and barely trust each other, which suits Costello fine.
11. What can Sullivan see from the windows of his new apartment?
- Fenway Park
- Boston Harbor
- The Bunker Hill Monument
- The State House dome
The gold dome of the Massachusetts State House, which the realtor pitches as the view of a man going places. Madolyn, the police psychiatrist played by Vera Farmiga, moves in with him while also treating Costigan, so the two men's lives cross unseen.
12. Which band performs I'm Shipping Up to Boston?
- The Pogues
- Rancid
- Flogging Molly
- Dropkick Murphys
The song appeared on their 2005 album The Warrior's Code, with lyrics taken from an unpublished Woody Guthrie notebook, and the film made it a Boston sporting anthem. Flogging Molly, among the distractors, are from Los Angeles and Rancid from the Bay Area.
13. What technology is involved in Costello's deal with Chinese buyers?
- Night-vision goggles
- Missile launchers
- Satellite dishes
- Microprocessors
Costello sells a crate of stolen microprocessors to Chinese government buyers in a warehouse handoff that both police units are watching. Each mole tips off his employer, the sting collapses, and the botched night is how both sides realize they have a leak.
14. What secret connection does Costello have to federal law enforcement?
- He once trained at Quantico
- He is working for the CIA
- He is an FBI informant
- He is a retired marshal
Whitey Bulger, the real boss Costello is drawn from, was a protected FBI informant for years while running Southie, and was finally caught in California after sixteen years on the run. The discovery changes how Sullivan sees his patron, and not for the better.
15. Which Oscar did Scorsese win personally for the film?
- Best Director
- Best Film Editing
- Best Supporting Actor
- Best Original Screenplay
His first win from six directing nominations, going back to Raging Bull, and Spielberg, Lucas and Coppola presented it together. The film took four in all, adding Best Picture, William Monahan's adapted screenplay and Thelma Schoonmaker's editing.

All the answers

1. Who directed The Departed?

Martin Scorsese

Scorsese marks the characters who are about to die with an X somewhere in the frame, a trick borrowed from Howard Hawks's 1932 Scarface. Brian De Palma, among the distractors, directed the 1983 remake of that film with Al Pacino.
2. Who plays undercover officer Billy Costigan?

Leonardo DiCaprio

Costigan's family ties to the Southie underworld make him useful, so Queenan and Dignam wipe his record and have him do real jail time on an assault charge to build the cover. It was DiCaprio's third film in a row with Scorsese.
3. Who plays police mole Colin Sullivan?

Matt Damon

Costello put Sullivan through school and steered him toward the state police, so he has a man inside before Sullivan has even graduated. Damon and DiCaprio had never worked together before, and the film keeps the two of them apart until the very end.
4. Who plays crime boss Frank Costello?

Jack Nicholson

Nicholson had never worked with Scorsese before and improvised much of the part; producing a pistol at the table during his talk with Costigan was his idea, and DiCaprio's alarm is genuine. Costello is loosely drawn from Whitey Bulger, the South Boston boss.
5. Which city is the main setting?

Boston

South Boston specifically, Costello's home turf, though much of the shoot was done in New York with Boston landmarks dropped into the backgrounds. Damon, from Cambridge, and Wahlberg, from Dorchester, are the ones with the real accents.
6. Which Hong Kong film supplied the main story?

Infernal Affairs

Andrew Lau and Alan Mak's 2002 thriller, with Tony Leung as the undercover cop and Andy Lau as the mole, had a prequel and a sequel before Hollywood got to it. Election is Johnnie To's triad film; A Better Tomorrow and Hard Boiled are John Woo's.
7. What does Costigan order at the bar, earning a joke at his expense?

A cranberry juice

A regular informs him it is a natural diuretic and asks whether he has his period, and Billy answers by breaking a glass over the man's head. Mr French, Costello's enforcer, played by Ray Winstone, breaks it up, and the brawl gets Billy noticed.
8. Which captain runs the Special Investigations Unit that Sullivan joins?

Ellerby

Ellerby, played by Alec Baldwin, later hands Sullivan the job of finding Costello's man inside the department, which is to say himself. Queenan, Martin Sheen's captain, runs the undercover operation with Dignam, Mark Wahlberg's permanently furious sergeant.
9. Which Rolling Stones song plays under Costello's opening monologue?

Gimme Shelter

Scorsese had already used it in Goodfellas and Casino; here it runs under Costello's speech about wanting his environment to be a product of him rather than the other way around. Monkey Man, among the distractors, is another Goodfellas track.
10. Which police organization employs Sullivan and Costigan?

Massachusetts State Police

Both men come through the same academy class, and the film is about troopers rather than Boston city cops. Queenan's undercover unit and Ellerby's Special Investigations Unit share a building and barely trust each other, which suits Costello fine.
11. What can Sullivan see from the windows of his new apartment?

The State House dome

The gold dome of the Massachusetts State House, which the realtor pitches as the view of a man going places. Madolyn, the police psychiatrist played by Vera Farmiga, moves in with him while also treating Costigan, so the two men's lives cross unseen.
12. Which band performs I'm Shipping Up to Boston?

Dropkick Murphys

The song appeared on their 2005 album The Warrior's Code, with lyrics taken from an unpublished Woody Guthrie notebook, and the film made it a Boston sporting anthem. Flogging Molly, among the distractors, are from Los Angeles and Rancid from the Bay Area.
13. What technology is involved in Costello's deal with Chinese buyers?

Microprocessors

Costello sells a crate of stolen microprocessors to Chinese government buyers in a warehouse handoff that both police units are watching. Each mole tips off his employer, the sting collapses, and the botched night is how both sides realize they have a leak.
14. What secret connection does Costello have to federal law enforcement?

He is an FBI informant

Whitey Bulger, the real boss Costello is drawn from, was a protected FBI informant for years while running Southie, and was finally caught in California after sixteen years on the run. The discovery changes how Sullivan sees his patron, and not for the better.
15. Which Oscar did Scorsese win personally for the film?

Best Director

His first win from six directing nominations, going back to Raging Bull, and Spielberg, Lucas and Coppola presented it together. The film took four in all, adding Best Picture, William Monahan's adapted screenplay and Thelma Schoonmaker's editing.