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The film opens in 1984. Ray Quick (Stallone) and Ned Trent (James Woods) are agents of the CIA and explosives experts. They have been tasked with assassinating a drug lord. When Ray notices that their target is accompanied by a little girl, he wants to call off the hit. Ned performs it anyway, killing both the drug lord and his girl. Ray is disgusted and quits their partnership and the agency. Ten years later, Ray has become a freelance assassin. Making a point of only killing specific targets, never bystanders. He also takes some cases for free, responding to requests by desperate people.
The latest such request comes from May Munro (Stone), a young woman who has an old grievance. While still underage, she witnesses the murders of both her parents by organized crime figures. Only because her father was a witness in some case. She was hiding in the closet and recognized one of the killers, Tomas Leon (Eric Roberts). He happens to be the only son and heir to a mob boss. Years later, she located him, seduced him and infiltrated his organization. Now she needs a partner to help assassinate him and hopefully bring the organization down as well. That Ned is part of said organization is added incentive for Ray.
The film was a box office hit, earning $170,362,582 in the worldwide market. Somewhat unexpected because Stallone had few major hits in the 1990s. The critics hated the film, pointing to unlikely situations and painful dialogues. At least James Berardinelli noted that the reason people liked it was because of having two great attractions: Sylvester Stallone's biceps and Sharon Stone's breasts.
This film provides examples of:
- Big Bad: Ned Trent.
- Career Killers: Ray Quick.
- CIA Evil, FBI Good: CIA doesn't mind collateral damage, nor killing children. That is what disgusts Ray.
- Dirty Business: How Ned Trent viewed the killing.
- Dirty Cop: Trent is getting paid by Leon Sr. to protect the organization from Quick.
- Does Not Like Shoes: May, who is barefoot at the film's climax.
- Dragon-in-Chief: Trent is the right-hand man of crime lord Joe Leon, but the latter is largely divorced from the plot, so Trent takes the role of Big Bad.
- Hoist by His Own Petard: Quick uses Trent's own bomb to set off the self destruct in his base when trapped by the police. This results in Trent being Blown Across the Room.
- Ironic Echo: In the beginning of the film taking place in 1984, Ned says this to Ray during their CIA mission:
Ned: Here's a tip: No fail-safe.
- Fast forward to 1994, Ray says the same exact thing to Ned near the end of the movie when Ned steps on a bomb causing the booby-trapped warehouse to blow up.
Ray: Here's a tip: No fail-safe.
Ned: Pressure pads?
- Kick the Dog: Supposedly the killing of the young girl at the beginning. Because aborting missions and wait for another opportunity sounds like a feasible option.
- Pay Evil Unto Evil: Ray supposedly only kills villains. May seduces and betrays her enemy. Even risking her own life to be there and watch his face as he dies.
- You Killed My Father: Actually both parents, but this why May hates Tomas so much. Enough to dedicate her life to vengeance.