The Thomas Crown Affair is a 1999 American romantic heist film directed by John McTiernan, written by Leslie Dixon and Kurt Wimmer and is a remake of the 1968 film of the same name.^[2][3] Its story follows Thomas Crown, a billionaire who steals a painting from an art gallery and is pursued by an insurance investigator with the two falling in love. It stars Pierce Brosnan, Rene Russo, and Denis Leary.

The film was produced by United Artists and Irish DreamTime and was released on August 6, 1999. It grossed $14.6 million during its opening weekend and $124.3 million worldwide, against a budget of $48 million.^[1] It received generally positive reviews from critics.^[4][5]

Thieves infiltrate the Metropolitan Museum of Art inside an actual Trojan horse, preparing to steal an entire gallery of paintings, but are apprehended. In the confusion, billionaire Thomas Crown – the crime's secret mastermind – steals Monet's painting of San Giorgio Maggiore at Dusk. NYPD Detective Michael McCann heads the investigation into the theft of the $100 million artwork, with the unwelcome assistance of insurance investigator Catherine Banning.

Crown lends a Pissarro to fill the Monet's space in the museum and falls under Banning's suspicion. She persuades McCann to begin surveillance of Crown, deducing that he is motivated not by money but the sheer thrill of the crime. Banning later accepts Crown's invitation to dinner.^[6]

At dinner, Banning has a copy of Crown's keys made; she and her team search his home and discover the Monet, which is revealed to be a taunting imitation painted over a copy of Poker Sympathy from the Dogs Playing Poker series. Banning confronts Crown, and the two give in to their mutual attraction and have sex.

Banning and Crown continue their cat-and-mouse game and their trysts, despite McCann's surveillance. Accompanying Crown on a trip to Martinique, Banning realizes he is preparing to run but rejects his offer to join him when the time comes. McCann presents Banning with photographs of Crown with another woman, Anna, complicating her feelings toward the case and her prime suspect. Banning and McCann discover that the fake Monet is in fact an expert forgery that could only have been painted by someone with access to the original; they visit the likeliest forger, Heinrich Knutzhorn, in prison, to no avail, although his body language suggests to them that he recognizes the work.

Later, Banning finds Crown packing his belongings with Anna. He promises Banning his interest lies with her alone, stating that Anna works for him but he would be compromising her to define the nature of their association. Crown offers to return the Monet by putting it back on the wall of the museum, and gives Banning a time and place to meet him when he's finished. Tearfully, Banning leaves and informs McCann.

The following day, the police stake out the museum, waiting to arrest Crown. Banning learns from McCann that the fake Monet was painted by Anna; the imprisoned forger Knutzhorn is her father, a former business partner of Crown, who became her guardian. Crown arrives and advertises his position in the lobby. The police realize that Crown expected Banning to turn him in and that he has set up another plot. Before the police can apprehend him, Crown blends into the crowd, aided by lookalikes in bowler hats à la Magritte's The Son of Man. Evading the officers, Crown releases smoke bombs and pulls a fire alarm, setting off the museum's fire sprinklers. His donated Pissarro, hanging in the Monet's place, is washed clean by the sprinklers to reveal the real Monet.

Crown's game is made clear: upon stealing the Monet, Crown had Anna forge the Pissarro over it and "returned" it to the museum. However, Crown has now vanished with another painting--one that Banning had told him she would have selected over the Monet. With the Monet recovered, Banning considers her role in the case concluded; the second missing painting is not covered by her employer. McCann briefly stops Banning to press her for anything she might know, but admits he has since stopped caring whether or not they catch Crown and bids her farewell. Banning then races to meet Crown at the rendezvous, but finds only a bowler-hatted courier who delivers to her the newly-stolen painting. Devastated, Banning has the painting sent to McCann and boards a flight back to London. In her seat after takeoff, she begins to cry when a hand from the row behind extends to her a handkerchief and offers her comfort. Recognizing the passenger's thinly-disguised voice, she turns to find Crown sitting behind her, and the two are reunited.

• Pierce Brosnan as Thomas Crown, a billionaire and Catherine's lover.
• Rene Russo as Catherine Banning, an insurance investigator and Thomas' lover.
• Denis Leary as Detective Michael McCann, a police detective.
• Fritz Weaver as John Reynolds
• Frankie Faison as Detective Paretti, a police detective.
• Ben Gazzara as Andrew Wallace
• Mark Margolis as Heinrich Knutzhorn
• Esther Cañadas as Anna Tyrol Knutzhorn
• James Saito as Paul Cheng
• Faye Dunaway as Psychiatrist
• Michael Lombard as Bobby McKinley
• Simon Jones as Accountant on phone (uncredited)^[7]
• Cynthia Darlow as Daria
• Daniel Oreskes as Petru

Dunaway played the Catherine Banning role in the 1968 original.^[8] However, the character's name was Vicki Anderson.

At first, director John McTiernan was unavailable for the project. Pierce Brosnan and his fellow producers considered several directors (including Mike Newell, Andrew Davis, Roger Donaldson) before returning to their original choice.^[9] McTiernan then received the script and added his own ideas to the production.^[10]

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The soundtrack was composed by Bill Conti and arranged by Jack Eskew. It features a variety of jazz arrangements which harken back to the original film's version. In addition, the film ends with a reprise of the Academy Award-winning song "Windmills of Your Mind" sung by Sting. Throughout the film, Nina Simone's recording of "Sinnerman" (from the album Pastel Blues, 1965) is used in segments. Mostly the non-vocal parts are used (hand-clapping and piano riffs), but in the final scenes, where Crown returns to the scene of the crime, Simone sings "Oh sinnerman, where are you gonna run to?"

In January 2007, it was announced that a sequel would be a loose remake of the 1964 film Topkapi.^[16] Pierce Brosnan said in January 2009 that Paul Verhoeven was attached to direct the film.^[17] In 2010, Verhoeven said that he had left the project due to script changes and a change in the regime.^[18] At one point, both Angelina Jolie and Charlize Theron were rumored for a part in the film, with Brosnan more keen on bringing Theron on board.^[19] In April 2013, Brosnan acknoweldged the film's status of being in development hell, but claimed he would still like to do it.^[20] The initial script was penned by John Rogers from a story he had co-written with Harley Peyton while additional material was provided by Nick Meyer, Michael Finch and Karl Gajdusek.

In the April 2014 edition of Empire, John McTiernan revealed that he had written a script for the sequel, while in prison, called Thomas Crown and the Missing Lioness.^[21]

In 2016, Michael B. Jordan had approached Metro-Goldwyn-Mayer to pitch a new adaptation of the story, with hopes of starring in the lead role.^[22][23] By April 2023 after previously acquiring MGM, Amazon announced plans to reboot the franchise, with a new feature film in development through the company's Amazon Studios.^[24]

• Heist film