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When Money Buys Trouble

From Brooklyn to the world, a chain of films where transactions turn tender, then treacherous.

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Anora (2024) is a fairy tale that curdles. Sean Baker's Brooklyn odyssey follows a sex worker who marries the son of a Russian oligarch, and the annulment mission that follows. It is a film about the fantasy of being rescued, and the brutal arithmetic that underpins it. Baker's genius is to make the transaction feel like love, then expose the ledger underneath. That tension, between the warmth of a connection and the coldness of its terms, is the engine of this chain.

The films that follow are not all about sex work or money, but they all share Anora's central question: what happens when a relationship is built on a deal? Each one takes a different kind of transaction, a marriage of convenience, a hired companion, a criminal bargain, and watches it mutate into something messier, more human, and more dangerous. The power imbalances are never tidy, and the exits are never clean. What binds them is the slow, uneasy realisation that the contract has been torn up, and no one knows the new rules.

This is a journey through different eras and settings, from 1970s New York to contemporary Seoul, but the emotional geography is constant. These are films about people who try to keep their hearts out of the deal, and fail. They are also films about how money distorts intimacy, and how intimacy can survive, or destroy, the transaction that birthed it. Watch them in order, and you will see the same story told in different keys: a cautionary tale, a tragedy, a thriller, a love story that refuses to behave.

Anora
1

Anora

2024 · dir. Sean Baker · 139 min

A Brooklyn sex worker marries the son of a Russian oligarch, and the fairytale turns into a battle when his parents arrive to annul it. Sean Baker's film is a screwball tragedy, alive with the energy of its streets and the desperation of its characters.

Anora Midnight Cowboy

The Link

Anora's Brooklyn is a world of hustle, and Joe Buck is another dreamer selling himself. Where Ani's transaction is a marriage, Joe's is a fantasy of being kept, and both films watch that fantasy collapse into something real and raw.

Midnight Cowboy
2

Midnight Cowboy

1969 · dir. John Schlesinger · 113 min

Joe Buck, a naive Texan, heads to New York to become a hustler for rich women, but ends up forming an unlikely partnership with the sickly con man Ratso Rizzo. Theirs is a transaction of survival that grows into a profound, aching friendship.

Midnight Cowboy Klute

The Link

Where Ani's marriage is a sudden gamble, Bree's work is a long-standing arrangement, and both women find their control slipping when a man enters the picture. Klute turns the transaction into a psychological thriller, asking what happens when the client starts to see the person.

Klute
3

Klute

1971 · dir. Alan J. Pakula · 114 min

A call girl in New York becomes entangled with a private detective investigating a missing executive. Jane Fonda's Bree is a woman who controls her transactions, until the detective's presence begins to unravel her carefully managed life.

Klute Bitter Moon

The Link

The transaction here is not just economic but emotional, a couple who use each other for pleasure and pain. Bitter Moon takes the power imbalance in Anora and pushes it to its most extreme, showing how a deal can become a cage.

Bitter Moon
4

Bitter Moon

1992 · dir. Roman Polanski · 139 min

On a cruise ship, a disabled man tells a young couple the story of his obsessive relationship with his wife, which began as a sexual transaction and spiralled into sadomasochistic games and mutual destruction. Roman Polanski's film is a dark, erotic study of power.

Bitter Moon The Piano Teacher

The Link

Like Bitter Moon, this is a transaction written in explicit terms, but here the contract is the film's centrepiece. The Piano Teacher shows how a deal for power can become a desperate plea for connection, and how the terms can be impossible to fulfil.

The Piano Teacher
5

The Piano Teacher

2001 · dir. Michael Haneke · 131 min

A repressed piano teacher at a Viennese conservatory enters a sadomasochistic relationship with a young student, drawing up a contract of humiliations. Isabelle Huppert's performance is a masterclass in controlled fury, as the transaction becomes a battlefield for her own demons.

The Piano Teacher In the Realm of the Senses

The Link

From The Piano Teacher's clinical sadomasochism to Oshima's raw, transgressive carnality, both films explore how desire becomes a battlefield where intimacy and domination blur. The shift from Vienna's bourgeois repression to 1930s Japan's militaristic society intensifies the stakes, leading naturally to In the Mood for Love's restrained, unspoken longing.

In the Realm of the Senses
6

In the Realm of the Senses

1976 · dir. Nagisa Ōshima · 102 min

Nagisa Oshima's controversial masterpiece, based on the true story of a maid and her master whose obsessive affair escalates to mutual destruction. The film's explicit sexuality is inseparable from its critique of power, possession, and the commodification of desire.

In the Realm of the Senses In the Mood for Love

The Link

The transaction here is emotional, a mutual agreement to share loneliness. In the Mood for Love takes the intimacy of Anora and strips away the sex and money, leaving only the ache of a connection that can never be consummated.

In the Mood for Love
7

In the Mood for Love

2000 · dir. Wong Kar-Wai · 99 min

Two neighbours in 1960s Hong Kong discover their spouses are having an affair, and they begin a careful, platonic relationship to understand what happened. Their connection is a transaction of consolation, but it deepens into an unspoken, impossible love.

In the Mood for Love Decision to Leave

The Link

The transaction here is the investigation itself, a series of interrogations that become a courtship. Decision to Leave takes the power imbalance of Anora and inverts it, as the detective's authority dissolves into fascination, and the widow's vulnerability becomes a weapon.

Decision to Leave
8

Decision to Leave

2022 · dir. Park Chan-wook · 139 min

A detective investigating a man's death becomes obsessed with the widow, who may be a suspect. Their relationship is a transaction of suspicion and attraction, and it blurs the line between investigation and intimacy. Park Chan-wook's film is a hypnotic noir of longing.

Where this chain leads

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