Colin Sullivan (Matt Damon) is introduced to organized crime by Irish-American mobster Frank Costello (Jack Nicholson) in the Irish neighborhood of South Boston. Costello trains him to become a mole inside the Massachusetts State Police. Sullivan is accepted into the Special Investigations Unit, which focuses on organized crime.
Before he graduates from the police academy, Billy Costigan (Leonardo DiCaprio) is asked by Captain Queenan (Martin Sheen) and Staff Sergeant Dignam (Mark Wahlberg) to go undercover, as his family ties to organized crime make him a perfect infiltrator. He drops out of the academy and does time in prison on a fake assault charge to increase his credibility.
As both men infiltrate their respective organizations, Sullivan begins a romance with psychiatrist Madolyn Madden (Vera Farmiga). Costigan sees her for his probation and develops a relationship with her, as well. After Costello escapes a sting operation, both moles become aware of each other’s existence. Sullivan is told to find the “rat” and asks Costello for information to determine who is the informer within his crew.
Costigan follows Costello into a cinema, where Costello gives Sullivan an envelope containing personal information on his crew members. Costigan then chases Sullivan through Chinatown. When it is over, neither man knows the other’s identity. Sullivan has Queenan tailed to a meeting with Costigan, and Costello’s men kill Queenan. When they exit, Costigan pretends he has come to join them. Later, Costello’s henchman, Fitzgibbons (David O’Hara), reveals that Delahunt (Mark Rolston), a crew member, was an undercover cop. Dignam is forced to step down as a consequence.
It’s a brilliantly constructed game of cat and mouse with each playing the respective role at one point in time. Filled with brilliant visuals that echo the themes of the script adapted by William Monahan from the script by Siu Fai Mak and Felix Chong the film manages to stay true to the elements that worked best in the Chinese film while incorporating elements unique to The Departed. DiCaprio and Damon give complex, compelling performances as opposite sides of the same coin.
Director: Martin Scorsese
Year of Release: 2006
Character to watch: Matt Damon as Colin Sullivan.
Journal your answers to the following questions after you watch the movie.
- How does this particular character’s journey compare with yours?
- Did the character develop certain characteristics during the movie that you have or that you would like to have? If so, what are those characteristics?
- What obstacles did this character face? What was his or her biggest challenge?
- What would you have done differently if you had been in the same position as the character?
- Is this character the type of person you would be friends with? Why or why not?