Played by: William Petersen
- "I'm gonna bag Masters, and I don't give a shit how I do it."
- Anti-Hero: A Sociopathic Hero at best and an arguable Villain Protagonist at worst.
- Bad Cop/Incompetent Cop: Chance screws up multiple times in the film, gets multiple people killed including himself, and is effortlessly manipulated by Masters.
- Boom, Headshot!
- The Hero Dies: If he can be considered as one, that is.
- Idiot Hero: Chance never thinks about the consequences of his actions at the best of times, but taking the handcuffs off of Cody is astonishingly stupid.
- Jerk with a Heart of Gold: Chance is an extremely abrasive risk-obsessed Cowboy Cop, but he strongly believes in friendship and partnership, and is sympathetic when Cody claims his daughter is sick in hospital. These values bring Chance nothing but misery.
- Meaningful Name
- Police Brutality: Prone to doing this.
- Psychopathic Manchild: His genuinely scary glee after the car chase and during his rape of Ruth reeks of this.
- Rabid Cop: A particularly rabid Secret Service agent.
- Revenge Before Reason
- Sociopathic Hero
- Villain Protagonist
Played by: John Pankow
- By-the-Book Cop: To a certain degree.
- After meeting Chance at his house following the discovery of Jimmy Hart's murder, he agrees with Chance's statement "I'm gonna bag Masters, and I don't give a shit how I do it", not knowing that it's Not Hyperbole.
- He chastises Chance for stealing Max Waxmans little black book after the Pasadena P.D responds to Waxmans murder by Masters for attempting to rip him off, stating that the police would have let them copy it after it was booked into evidence.
- He does state however that he is not a snitch in response to Chance questioning his resolve as his partner.
- During the chase and shakedown of two small time credit card thieves, Vukovich gives the thief he was chasing a nasty kick in the back after forcing him against a chain link fence for questioning.
- He vehemently objects to Chances proposal to rob fence and undercover F.B.I. Agent Thomas Ling of his $50,000 in order to get the front money to pay for Masters counterfeit money, but eventually agrees after being bullied into it by Chance.
- He initially picks up and slaps Masters back to the ground before drawing Chance's gun and aiming at him, but still can't bring himself to shoot Masters in cold blood. This give Masters the opportunity to grab a plank of wood and beat Vukovich to the ground with it. He then covers Vukovich in shredded paper with the intention of setting him on fire but is shot in the gut by Vukovich before Masters has a chance to, causing him to drop the lit piece of paper into the puddle of gas that Masters happened to be standing in.
- Heroic BSoD
- Took a Level in Jerkass: The botched robbery and Chance's death traumatize him to the point that he ends up killing Masters, completely pushing him over the edge into becoming the same kind of rabid cowboy cop that Chance was.
Played by: Willem Dafoe
- Anti-Villain: Keeps his word, and never breaks a contract. Woe to those who fail to do either.
- Bad Boss: Tries to have Cody killed in prison.
- Cruel and Unusual Death: An exceptionally gruesome example in that Vukovich shoots Masters in the gut with Chance's revolver, causing Masters to drop the lit piece of paper he was holding into the puddle of gas he happened to be standing in. This causes Masters to be engulfed in flames, as Vukovich empties the remaining five shots of .357 Magnum into Masters, yet Masters doesn't die from the gunshots and continues to scream in pain until he FINALLY falls over dead.
- Death Seeker: A common interpretation of his motivations.
- Evil Virtues: Takes extreme pride in his level of crafstmanship, and his reputation.
- The Unfettered
Played by: Debra Feuer
Played by: Dean Stockwell
Played by: Darlanne Fluegel
Played by: John Turturro
Jim 'Jimmy' Hart
Played by: Michael Greene
Played by: Robert Downey Sr.
Jack, Masters' bodyguard
Played by: Jack Hoar
- Cast the Expert: Actor Jack Hoar was a decorated LAPD officer who served as a Professional Consultant and liaison for the production.
- The Dragon
Played by: Steve James
Played by: Christopher Allport
Thomas Ling AKA F.B.I. Agent Raymond Fong
Played by: Michael Chong