20 Dark Romantic Films That Are Worth Your Time

7. Your Friends and Neighbors (1998)

YOUR FRIENDS AND NEIGHBORS, Amy Brennemann, Nastassja Kinski, Catherine Keener, 1998

Two American, professional middle class couples struggle with the unhappiness in their relationships. Jerry (Ben Stiller) is married to Terri (Catherine Keener) who is unsatisfied his sexual skills or lack of. They have dinner with Mary and Barry (Amy Brenneman and Aaron Eckhart) are also unhappy with their marriage and make it painfully obvious.

Afterwards, Jerry asks Mary discreetly for a date and she accepts out of her own frustration. Terri begins having a lesbian affair with Cheri (Nastassja Kinski) and prefers the silent lovemaking with her rather than her husband. Barry meets with his friend Cary (Jason Patric), a doctor who is a cruel, self-absorbed sexual deviant and tries to convince him to leave Mary for non-monogamous lifestyle that he leads.

Written and directed by Neil LaBute (who also did “In The Company of Men”), concocts a battle of the sexes that pulls the preverbal gloves off, striking above and below the belt. Hardly romantic, but definitely a black comedy dealing with the unhappiness of couples who fall out of love, sexual attraction towards each other or those that have no concept of compassion nor understand the needs of loved ones. Despite the less than uplifting subject matter, the film did well with critics and audiences.


8. B. Monkey (1998)

B. Monkey (1998)

In London, Alan (Jared Harris) is a professional school teacher who moonlights as a jazz DJ for a local hospital. At a bar, he is captivated by a beautiful woman named Beatrice (Asia Argento), as he witnesses her arguing with two men. He eventually learns is that she is a cat burglar known to the authorities as “B. Monkey”. She is at odds with Paul and Bruno (Rupert Everett and Jonathan Rhys Meyers), her roommates/partners in crime about leaving the life behind with hopes of finding love.

Starting off on an awkward foot, Alan and Beatrice begin dating, go on a holiday to Paris where they discover happiness in the straight life. However, when they return to Britain, all is not well with her criminal partners and Paul tries to convince her to pull off one last heist.

Loosely based on Andrew Davies’ 1992 British novel, the 1998 feature was directed by Michael Radford (“1984”). It was a satisfying sleeper hit on the indie circuit, but didn’t capture much attention in America. There were internal problems within the productions which made the storyline less coherent and much footage was shot that was never used along with multiple alternative endings.


9. Grosse Pointe Blank (1997)

GROSSE POINTE BLANK, John Cusack, 1997

Freelance and professional assassin, Martin Blank (John Cusack) is growing bored with his line of work and feels pressure from a rival hitman Grocer (Dan Aykroyd) to join in a partnership or risk being on the opposite end of the gun. His secretary, Marcella (Joan Cusack), informs Blank of his high school reunion in his home town of Grosse Pointe, Michigan, simultaneously with booking another contract.

At first he’s reluctant, but under the advice of his therapist (Alan Arkin), he heads home. Upon arrival, he meets up with his friend Paul (Jeremy Piven) and seeks out an old flame, Debi (Minnie Driver), whom he abandoned on prom night. However, he is being trailed by another assassin, two NSA agents and Grocer, all who are set on killing him.

Inspired by being invited to his Michigan high school reunion, Tim Jankiewicz, wrote the screenplay while being a substitute English teacher in California. Directed by George Armitage and released in 1997, containing a musical score by Joe Strummer and a soundtrack with two volumes with songs by the Clash, the Specials, the Violent Femmes, the Pogues and more.

In 2008, an informal sequel “War, Inc.” starring John and Joan Cusack with Dan Aykyord was shot and adheres many similarities to its predecessor.


10. Cruel Intentions (1999)

Kathryn Merteuil (Cruel Intentions)

In NYC, two wealthy, manipulative teenage step-siblings, Kathryn (Sarah Michelle Gellar) and Sebastian (Ryan Phillippe) discuss their final year of prep school. She has agreed to be the protector of Cecile (Selma Blair), a naïve new student and wants her step-brother to seduce the young girl out of vengeance for Kathryn’s ex-boyfriend ending their relationship.

Sebastian refuses at first, having his sights set on another target, the out-spoken, yet virginal and abstinent until marriage Annette (Reese Witherspoon) and the daughter of their school’s headmaster. The two step-siblings make a bet: if she wins, the prize is his vintage Jaguar car; if he wins, he gets to have sex with her. Meanwhile, he documents the progress of his daily life in a journal.

Director/screenwriter Roger Kumble’s 1999 romantic “dramedy” is a modern telling of Pierre Choderlos de Laclos’ novel, “Les Liaisons Dangereuses” from 1782. Upon its release, the film received mixed reviews, but gained a cult following and spawned two direct-to-video sequels. Roger Ebert was one the defenders and called it “smart and merciless” in the spirit of the original material.


11. Piano Teacher (2001)


In Vienna, forty-something Erika (Isabelle Huppert) is a piano teacher at a prestigious music school. She is single, but lives with her overprotective and domineering mother while her father is a resident at a mental health facility. When not under the thumb of her parents or pressures of the job, Erika indulges voyeuristic, sadomasochistic and self-mutilating behaviors. Enter Walter (Benoit Magimel), a charming, seventeen-year-old and a gifted piano player.

A mutual, obsessive attraction begins, despite her initial disinterest. Erika becomes jealous upon seeing that one of her female students fawning over Walter and sabotages the young girl’s performance (and future as a pianist) by causing injuries to her hands. Eventually, their affair begins, but only if Walter is willing to comply with his piano teacher’s masochistic desires of rape and abuse, meanwhile being subjected to her controlling and humiliating actions.

Based on the 1983 Austrian novel by Elfriede Jelinek, the 2001 French film was adapted and directed by Michael Haneke. It roots deeply into the disturbing psychosis brought on by loneliness, jealously, feelings of inadequacy, manipulative motives and sexual fetishes. Haunting, yet passionate and difficult to shake off.


12. One Night at Mccool’s (2001)

One Night at Mccool’s (2001)

Bar owner and tender, Randy (Matt Dillion), saves the beautiful Jewel (Liv Tyler) from being raped, only to have the assailant come back and she kills him inside the bar, McCool’s. Randy and Jewel form a relationship when he takes her back to his childhood home that he had inherited after his mother died.

As time progresses, she becomes very demanding and insists that he commit crimes and foot the bill for her expensive tastes. Meanwhile, his married cousin Randy (Paul Reiser) is sexually obsessed with Jewel. Then the investigating officer, Detective Dehling (John Goodman) is convinced that Randy is an abusive boyfriend and considers it his duty to save the illustrious woman, whom he too has become infatuated by.

Merging a screwball romantic comedy with film noir elements, Harald Zwart directs a screenplay by Stan Seidel, who died before the film was released in 2001. The three main male characters (Dillion, Reiser and Goodman) confide their stories to a hitman (Michael Douglas), psychiatrist (Reba McEntire) and a priest (Richard Jenkins), all of which have slight variations on the details.


13. The Rules of Attraction (2002)

The Rules of Attraction

At Camden College in New Hampshire, the lives of many spoiled and over-privileged students are in turmoil. Sean (James Van Der Beek) owes his cocaine dealer Rupert (Clifton Collins Jr.) a “fuck-ton of money” and is under pressure to move some product.

Would-be virgin Lauren (Shannyn Sossamon) pines for the shallow and rich Victor (Kip Pardue), who is on drug-fueled, ego trip throughout Europe. Paul (Ian Somerhalder) is openly bisexual, but leans more towards being gay, used to date Lauren, but now sets his sights on Sean, who seems oblivious to his advances. Bizarre love triangles form and tensions heat up as a long, cold winter approaches.

Based on Bret Easton Ellis’ 1987 darkly comedic satire on college life was adapted for the screen and directed by Roger Avary (co-writer of “Pulp Fiction”). Slight plot changes and character shifts were applied to condense the storyline. Cameos from Faye Dunaway, Swoozie Kurtz, Paul Williams and two members of Bananarama lighten the mood of the chaos. Of all the films that have been spawned from his books, author Ellis feels that “The Rules of Attraction” remains the most faithful to the original source material.