In 1984, CIA operatives/explosives experts Ray Quick (Stallone) and Ned Trent (Woods) are assassinating a drug lord by detonating a bridge he'll be driving over. When Ray notices that their target is being accompanied by a little girl, he attempts to call off the hit. Ned performs it anyway, killing both the drug lord and his girl. Ray is disgusted and brutally beats up Trent before quitting the agency...
Ten years later, Ray has become a freelance assassin who kills specific targets while ensuring that bystanders aren't injured. He also takes some cases for free, responding to requests by desperate people. The latest request comes from May Munro (Stone), a young woman who saw her parents murdered in front of her when she was young, and has sworn vengeance against their killers, including Tomas Leon (Eric Roberts), the son and heir to Miami mob boss Leon Sr. (Rod Steiger).
Ray initially refuses to consider May's request, but changes his mind when he learns the story behind what happened to her. Complicating matters are that Trent (now an ex-CIA security consultant) is working for the Leon family. Things are set for a collision course between Ray, May, Trent and the rest of the Leon family...
This film provides examples of:
- Aroused by Their Voice: Ray and May enjoy listening to each other speak; so much so that they not only have long conversations on the phone, but Ray listens to recordings of her while working out, and May conducts at least one phone call while wandering around her apartment in sexy lingerie and high heels, with soft mood lighting and romantic music playing in the background.
- Black and Grey Morality: While Ray is the nominal hero of the film, he's also a Professional Killer who murders people more evil than himself for money while avoiding civilian casualties. In contrast, Trent is an ex-CIA operative who isn't above doing whatever he needs to get the job done, no matter the cost.
- Blown Across the Room: What happens to several of Ray's targets. Granted, he is using explosives, but still...
- Chewing the Scenery: Holy cow, James Woods must have crapped Kodak film reels after this role.
- CIA Evil, FBI Good: The CIA doesn't mind collateral damage, nor killing children. That is what disgusts Ray.
- Crazy-Prepared: Not only does Ray take out his targets with elaborate methods (including wiring a car garage keypad to take out the occupant of a specific car and using an explosive teacup), but his compound is wired with boobytraps and he possesses the means to wire an apartment for demolition with only a couple minutes' notice beforehand.
- Dirty Business: How Ned Trent views 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.
- Evil Is Hammy: Ned, who delivers his lines in an over-the-top, mustache-twirling fashion.
- Faking the Dead: May, complete with a staged funeral.
- Feet-First Introduction: May is introduced stepping out of a limousine at a high-society party, with the camera panning up from her feet.
- HeelFace Revolving Door: May is initially set up as a distraught woman who asks Ray to take out the three men who were responsible for murdering her parents... then it's revealed that she's secretly working for Trent, and has cut a deal with him to take out the top brass in the Leon family in order to lure Ray into the open so Trent can kill him. Then she falls in love with Ray, and joins his side to take out Trent during the climax of the film.
- Hitman with a Heart: Ray, who only goes after outright villainous individuals, and will sometimes take on cases pro bono for clients who don't have the financial means to pay him.
- I Have You Now, My Pretty: Trent towards May, to the point that he gropes her several times when they're in proximity of each other.
- 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.
Ray: Here's a tip: No fail-safe.Ned: Pressure pads?
- 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.
- Kick the Dog: The killing of the young girl at the beginning.
- Leave the Camera Running: The final shot of the film, as May and Ray drive away past a bridge while framed by the Miami skyline.
- Mysterious Employer: Ray himself is this, as he only communicates with his contacts via an online messaging system and refuses to meet face-to-face.
- Oh, Crap!: Happens several times to those on the receiving end of Ray's bombs, including Tony and Trent himself after the Ironic Echo.
- Only in It for the Money: Invoked by Trent during his opening conversation with Tomas, where after being offered an "advance" for his latest job, he throws it back in the latter's face and tells him he doesn't work for tips before asking them to pay the full amount upfront.
- Outrun the Fireball: During the climax, when Ray and May have to escape his exploding compound.
- 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.
- Professional Killer: Ray Quick. His specialty is explosives, making him also a Professional Mad Bomber.
- Properly Paranoid: Ray's compound is littered with failsafes in case it were ever breached, including multiple pressure pads, scanning tech and explosives wired throughout the building (which can only be deactivated by him).
- Rage Against the Heavens: Leon Sr.'s final action upon noticing the bomb he just triggered within May's necklace is to look up and yell at God "You bastardo!". Considering that one second before he was thanking Him for killing Ray and May
- Revenge Before Reason: May's rationale for being present in the same room as Tomas when he's killed by the explosive teacup, despite the fact that it seriously injures her in the process.
- Shower of Love: Ray and May have sex in the shower.
- Smoking Is Cool: Tomas is seldom seen without a cigarette or cigar, and very obviously considers himself to be an ubercool toughguy.
- Smoking Is Glamorous: Sharon Stone smokes constantly throughout the film, and in several scenes it is done in a very sexual, sensual fashion.
- Soft Water: A bomb in a hotel room launches someone through a window and into the sea, but he seems unharmed by either the blast or the fall. Then the hotel room itself falls on him.
- Victoria's Secret Compartment: When Ray finally meets May at the funeral home, he frisks her and discovers a small handgun hidden in the band of her stockings.
- Would Hurt a Child: Trent goes through with the hit against the drug lord in 1984, which kills a child in the process. That Trent is willing to do this on behalf of the CIA is the final straw for Ray, who beats him senseless, ruins his reputation and quits the agency in disgust.
- You Have Outlived Your Usefulness: Invoked by Trent when he muses out loud over whether May has outlived her worth to him
- You Killed My Father: Actually both parents, but this why May hates Tomas so much—enough to dedicate her life to vengeance.