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William ‘Billy’ Costigan Jr
Played By: Leonardo DiCaprio
"You sit there with a mass murderer. A mass murderer. Your heart rate is jacked, and your hand... steady. That's one thing I figured out about myself in prison. My hand does not shake... ever."
A South Boston Police Officer who is selected to become a mole in Frank Costello's organisation.
- Anti-Hero: He has to do some really shady things while undercover, such as participating in murder.
- Boom Head Shot: How he was killed by Barrigan.
- Cultured Badass: He actually went to decent schools and got excellent grades as noted by Dignam and Queenan, he could actually have had a better career but he really wants to be a cop. He also quotes Nathaniel Hawthorne.
- Deadpan Snarker: Another defense mechanism to deal with the stress of being undercover
- Didn't See That Coming: There's no way he could have anticipated being taken down like that. He called for backup by calling Brown, he mailed the evidence(making copies) and sent it to the police shrink but it takes a Giant Space Flea from Nowhere, a second mole, to take him out with no warning.
- Foil: To Sullivan.
- Good Is Not Nice: He's quite abrasive, contrasting to the usually calm Sullivan
- Hair-Trigger Temper: He's like this as the result of the stress of being a mole.
- The Hero: As the film's protagonist
- Heroic BSOD: He's utterly devastated when Queenan dies in front of him.
- Jerk with a Heart of Gold: His jerk behavior is due to the stress of being undercover within the organization of a murderous madman like Costello
- The Mole: He's a mole for the Boston Police inside Costello's organisation.
- Sanity Slippage: Due to the stresses of being undercover and then by Queenan's death.
- Sixth Ranger Traitor: To Costello.
- Surprisingly Sudden Death: He's killed by a shot to the head instantly and with no warning whatsoever.
- Unperson: When Sullivan erases all records of him being an undercover.
- Troubled, but Cute: According to Madolyn.
Staff Sergeant Colin Sullivan
A member of Frank Costello's criminal organisation sent to infiltrate the Boston Police Department.
- Asshole Victim:
- Boom, Headshot: Given to him by Dignam. He gives one to the Mole who whacked Costigan as well.
- Bitch in Sheep's Clothing: Even though he's Costello's mole, he keeps a squeaky clean record to ascend and avoid suspicion
- Detective Mole: He's charged with finding the mole in the Boston police department - himself.
- Dirty Cop: He's Costello's mole inside the Massachusetts State Police.
- Disappeared Dad: Costello takes over
- Evil Genius: For Costello
- Foil: To Costigan.
- Hired to Hunt Yourself: Tasked with finding Costello's mole: himself
- Jerkass: What he is at heart. Though he's genuinely a decent boyfriend to Madolyn, until she finds out that he's a mole, she doesn't consider breaking up with him, even hoping to start a family with him with a child that may or may not be his.
- Mole in Charge: When he takes over Queenan's unit.
- Professional Butt-Kisser: How the rest of the cops see him
- Raised Catholic: Like most Irish-American kids. The Prolonged Prologue has a shot of him serving as an altar boy. note .
- The Starscream: He ends up betraying and killing Costello after finding out Costello's an FBI informant and was ready to expose him to the feds.
- Ungrateful Bastard: To Costello
- Wicked Cultured: As a young boy he gets a James Joyce reference and later discusses Freud seriously with a shrink. More to the point he wants to study law and apply himself and make it into Harvard, and maybe become legitimate.
- Villainous Breakdown: At the near end when he's caught by Costigan.
Captain Oliver Charles Queenan
The Captain of the Boston Police Department.
Staff Sergeant Sean Dignam
Played By: James Badge Dale
Francis "Frank" Costello
A ruthless and infamous old mobster targeted by the Boston Police Department.
- Bad Boss: He constantly threatens to murder his underlings if they displease him. He kicks it up a notch at one point with Sullivan, threatening to have his girlfriend raped if he doesn't find the mole.
- Chronic Backstabbing Disorder: Frank is betraying his own men to the FBI, taping Sullivan so he can give him up if the need arises, and screws the Chinese government over on a deal for stolen missile technology.
- Dirty Old Man: In his first scene, he hits on a teenager by asking if she's had her period yet. Later, he makes a pass at a nun.
- Faux Affably Evil: He comes across as a charismatic guy for at most, a few seconds, before revealing what a depraved psychotic he truly is.
- For the Evulz: The reason he truly does what he does. At his core, Frank is a sadist.
Billy: You don't need the money.
Costello: I haven't "needed the money" since I took Archie's milk money in the third grade. Tell you the truth, I don't need pussy any more either... but I like it.
Mr. Arnold "French"
Costello's most trusted enforcer.
Played By: David O'Hara
A slightly dim but intimidating henchman of Costello.
Played By: Mark Rolston
One of Costello's top thugs.
Dr Madolyn Madden
A psychiatrist who Costigan sees under the terms of his probation.
Played By: Kevin Corrigan