Romeo Is Bleeding

Romeo Is Bleeding is a 1993 neo-noir crime thriller film directed by Peter Medak, written and produced by Hilary Henkin, and starring Gary Oldman, Lena Olin, Annabella Sciorra, Juliette Lewis, and Roy Scheider. It follows a psychosexual cat-and-mouse game between a corrupt cop (Oldman), and a ruthless mob assassin (Olin) who begin to fall in love. The film's title was taken from a song by Tom Waits.

Released in the United States by Gramercy Pictures, the film was critically unsuccessful and did not perform well at the box office (grossing $7 million from a $10 million budget), although its acting has garnered praise.

Jack Grimaldi is an NYPD homicide detective who seems to have everything: a lavish lifestyle; a beautiful wife, Natalie; and an adoring teenaged mistress, Sheri. However, Jack only affords his lifestyle because he's on the take, doing favors for Mafia boss Don Falcone in exchange for large cash bribes. Jack's latest task is to reveal the location of Nick Gazarra, a mobster-turned-state's witness protected by federal agents. Gazarra and his protection detail are subsequently killed by a mob hitwoman, Mona Demarkov. Jack is disaffected by this outcome, being uncomfortable with his complicity in the deaths of other law enforcement personnel.

Mona is arrested and Falcone assigns Jack to kill her, as he fears that she could not only testify against him but take over his entire operation. Still ambivalent about his double life, Jack is assigned as Mona's minder and transports her to a safe house to await pick-up by federal agents. Upon arrival, Mona quickly seduces and tries to kill Jack, but they are interrupted by the agents. Jack leaves Mona in their custody.

Falcone, disappointed in Jack's ineptitude, orders one of his toes amputated. Realizing he has endangered both his wife and mistress, Jack instructs Natalie to leave the city immediately, giving her all of the payoff money he has saved as well as instructions for where to meet him out West when the time is right. Jack also ends his affair with Sheri and puts her on a train out of town. He tracks down Mona, who offers to pay Jack to help her fake her own death.

Although he obtains false papers for her, Mona refuses to pay and attempts to strangle Jack. He shoots her in the arm, then tries to drive away with her handcuffed in the back seat. Mona escapes by hooking her legs around his neck, causing him to crash the car. She slithers out through the shattered windshield without freeing her hands. Mona lures Jack to an empty apartment. He again attempts to kill her but is tricked into shooting Sheri instead. Mona fixes the corpse so as to suggest that it was she, and not Sheri, who died. Mona has Jack abducted and transported to an abandoned warehouse where she handcuffs him to a bed and they have sex. Later she forces Jack to assist in burying Falcone alive.

Mona betrays Jack by turning him in to the police, copping a plea deal that will indict Jack for the multiple murders that she tricked him into committing. The police arrange a confrontation between Jack and Mona at the courthouse. Mona tells Jack sex with him was lame, that Jack's wife "is a dead woman" and that Jack himself "is a dead man". Furious, Jack grabs a gun from a fellow officer's ankle holster and shoots Mona dead. He turns the gun on himself, only to discover that the revolver is now empty. Instead of being sent to prison for the murder, he is given a commendation. This frees him to begin a new life out West, under the identity of "Jim Daugherty".

The final scene shows Jack living alone in a remote desert town and working at a diner. He waits every May 1 and December 1 for his wife, Natalie, to find him, as they planned before she left; but she never does. As he waits for her, he mourns his old life while looking at his wedding photo album: first, the many color photos of himself and Natalie, followed by black and white Polaroids of his various paramours, including Mona.