Blackmail. It’s one of those things you hope you will never be subjected to, although it can be used against just about anyone, whether you’re a kindergartener whose classmate saw you steal an eraser, a housewife stepping out on her husband who’s been spotted by a neighbor, or any manner of government official hoping that no one will peek into their past.
Whatever the reason behind the blackmail, whatever the price put upon the information, there are a few reactions that the blackmailed can have: pay the price, tell the authorities, or try and wiggle their way out of it. These are the 10 best movies about blackmail and blackmailers, secrets and lies, victims and perpetrators.
10 Derailed (2005)
Based on a thriller by James Siegel, Derailed stars Clive Owen as Charles, a married man who meets an attractive woman, Lucinda (Jennifer Aniston) on his commute. After a flirtation, they decide to take things a step further, but upon meeting at a hotel, they are subjected to a horrific attack by an intruder. Desperate to keep their almost-affair a secret, the pair intend to keep quiet about the attack and merely not see each other again, but the attacker, La Roche (Vincent Cassel), soon surfaces, with threats of exposing the relationship if he’s not given a large sum of money. Charles’ only option for getting the money is to empty a fund intended for his daughter’s medical treatment, and things are about to get worse when he discovers Lucinda’s true identity.
9 Devil in a Blue Dress
Denzel Washington stars as Easy Rawlins in this adaptation of a Walter Mosley mystery, on the hunt for a missing woman with a rich fiancé at the behest of a private investigator in 1940s Los Angeles. With the help of his pal Mouse (an award-winning Don Cheadle), Rawlins quickly finds himself in over his head, harassed over the murder of an acquaintance who was the woman’s friend. It soon comes to light that Daphne (Jennifer Beals) is alive and involved in a complicated plot wherein her fiancée’s political career was in trouble due to the revelation of Daphne’s mixed-race heritage, but that Daphne was blackmailing the man who was threatening to release that information with his own dark secret.
Money changes hands, and a few people are murdered, but the whole thing ends surprisingly well given the blackmail plot, with Rawlins deciding that he might as well become a full-time private detective.
8 The Drowning Pool (1975)
In this sequel to Harper, Paul Newman reprises his role as dissolute P.I. Lew Harper, and this time the case involves a married ex-lover, Iris Devereaux (played by Newman’s wife, Joanne Woodward). Iris is being blackmailed over her infidelities by, she thinks, the family chauffeur, and enlists Harper’s help. While investigating in Louisiana, the situation gets more and more complicated, with oil magnates, murders, and Iris’ seductive teenage daughter, Schuyler (a young Melanie Griffith).
The chauffeur is killed by masked gunmen, officially ruling him out as a suspect, and Harper is quickly in over his head, and not just with the Devereaux women. Harper is kidnapped and nearly drowned, but he persists in tracking down the real blackmailer, who ends up being from an unexpected corner. The whole movie has the humid, heavy atmosphere of the South, which adds to the aura of suspense.
7 L.A. Confidential (1997)
Guy Pearce and Russell Crowe hit the Hollywood scene in this neo-noir adaptation of a James Ellroy novel, playing 1950s L.A.P.D. detectives Exley and White alongside Kevin Spacey as Vincennes. Exley is unpopular in the department given his habit of ratting out corrupt cops; White has a virulent hatred of domestic abusers due to family history, and Vincennes is aided by the publisher of a tabloid magazine, tipped off with scandalous, not-always-true information about celebrities behaving badly, leading to high profile arrests.
Vincennes gets in too deep with his tabloid contact, who is using photographs of arranged scandals in a blackmail scam, and his growing conscience gets him killed by a superior. Kim Basinger co-stars as a Veronica Lake lookalike, for which she won a Best Supporting Actress Oscar, and the film still holds up as one of the best neo-noirs ever made.
6 Burn After Reading (2008)
This star-studded Coen brothers outing let a number of actors exercise their comedy skills: John Malkovich is the gloomy Osborne Cox, a newly ex-CIA analyst writing his memoirs and married to Katie (Tilda Swinton), who’s having an affair with U.S. Marshal Harry (George Clooney). Katie submits a disc of Osborne’s info (including his memoir draft) to her lawyer while filing for divorce, and the lawyer’s accidentally leaves it in a gym locker, where it is discovered by opportunistic personal trainer Chad (Brad Pitt) and his colleague, plastic surgery obsessed Linda (Frances McDormand).
The pair’s bumbling attempts to blackmail Osborne for the return of what they believe to be highly sensitive information are both disastrous and more successful than they could have imagined: they alert what turns out to be a CIA agent undercover at the Russian embassy, leading the U.S. government to suspect a game of high-stakes espionage is afoot. Confusion abounds with hilarious results in this darkly satirical romp about intelligence, fidelity, and deceit.
5 The Big Sleep (1946)
Humphrey Bogart played Raymond Chandler’s iconic private detective Phillip Marlowe opposite his soon-to-be-wife Lauren Bacall in this Howard Hawks-directed tale of blackmail and murder. Bacall was Vivian Rutledge, whose wealthy father has charged Marlowe with helping out his younger daughter, who, it turns out, is being blackmailed over some shocking photographs. But there’s also a missing protégé, previous instances of blackmailing, failed seductions, and murders. The plot is notoriously hard to follow, given plot devices in the novel that wouldn’t have passed the Hays Code, and Bogart’s ongoing alcoholism and personal issues. But it did nothing to lessen the fascination of the public with the Bogart/Bacall love story.
4 The Letter (1940)
Bette Davis takes on the role of murderess in this drama based on a play by W. Somerset Maugham, which in turn was based on real events that took place in Kuala Lumpur in 1911. The scene is set in Malaya, where Davis plays Leslie, the wife of a plantation owner, and one night when he is away, Leslie saves herself from attack by killing an ex-pat named Geoffrey Hammond.
She’s arrested but seems likely to be acquitted until it comes to light that the night of the murder, she wrote a letter to Hammond, asking him to come visit her. Hammond’s widow has ended up with the letter, and through a servant, she communicates to Leslie’s lawyer that she’s willing to part with it, but only for a very high price. Leslie forces the lawyer to make the purchase, and she is indeed acquitted, but it soon becomes clear she will not escape justice for long.
3 Dangerous Liaisons (1988)
Glenn Close and John Malkovich are at their best as former lovers Marquise de Merteuil and Vicomte de Valmont in pre-Revolution Paris in this sumptuous period piece based on the 1782 novel by Pierre Choderlos de Laclos. Rich and bored, the pair spend their time seducing, gambling, and wreaking vengeance on those who have wronged them. They embark upon a bet that stipulates the Marquise will sleep with Valmont provided he can prove that he’s slept with a notoriously religious beauty, Madame de Tourvel (Michelle Pfeiffer).
The Marquise also gets Valmont to ruin the honor of a young beauty, Cécile (Uma Thurman), which he accomplishes through blackmail. An intricate series of betrayals and set-up seductions are put into action by the scheming pair, but what starts out as devious entertainment ends up with the downfall of almost everyone unwittingly involved.
2 Strangers on a Train (1951)
Hitchcock’s chilling retelling of Patricia Highsmith’s novel stars Farley Granger and Robert Walker as Guy Haines and Bruno Antony. The two men strike up a conversation on a train, and it’s revealed they both have someone they want out of their lives: Haines could do without his unfaithful wife, so he can remarry, and Antony wishes to be rid of the father he loathes. Antony brings up the idea that each could murder the other’s tormentor, which would remove the motive, an idea that Haines brushes off, leaving his cigarette light behind when they part ways. Much to Haines’ surprise, his wife turns up dead, and Antony resurfaces to blackmail Haines into completing his half of the deal he never actually agreed to.
1 Clue (1985)
Clue is a classic for a reason: it's fantastic. With a picture-perfect cast (Tim Curry, Madeline Kahn, Michael McKean, etc.), the black comedy is based on the board game, with the backstory being that a dinner party is being thrown wherein all the guests are being blackmailed by a mysterious host. The guests, who all have government connections in Washington, D.C., are trying to figure out why they’ve been invited when murders start to occur, and there are definite overtones of Agatha Christie and locked-room mysteries as the guests bicker and panic while trying to find out who among them is the murderer (or murderers). It’s a fast-paced, madcap murder mystery with multiple endings that has amassed a well-deserved cult following over the years.