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Catherine Banning: Do you really think I am going to sleep with the man I am investigating?

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Mistakes

In the opening sequence, when Crown decides to walk and has "Jimmy" meet him at the office, he is almost run down by a truck. First of all, the truck has to skid to a stop, yet there is a car no more than ten feet in front of it when they change camera angle. Why was the truck going so fast in the first place. Secondly, when Crown motions for the driver to pass, the same car is still stopped directly in front of the truck, yet the truck speeds off in a way that it should smash into the car in front of it. See more...

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In the ball scene when Pierce Brosnan dances with Rene Russo you will notice that Pierce Brosnan's tie is never tied. It was part of his contract as being James Bond that he not wear a full tuxedo in any other movie.
Edit Submitted by Heather Singh
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The painting that is seen several times in the film depicting a man in a suit with an apple covering his face is "Son of Man", by Rene Magritte.
Edit Submitted by Ral0618
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Not strictly a mistake, but have you ever seen anything like the product placement when Rene Russo storms into an office and downs a can of Pepsi One (with the label cunning facing the camera)? She does all but turn to camera, hold it up, and say "aaah - there's nothing like an ice-cold can of Pepsi". I actually laughed when I saw it.
Edit Submitted by Jon Sandys
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The dress that Rene Russo wears that is transparent in the dance scene actually belonged to the actress that played Thomas Crown's protege Anna. She wore it to the set on a lark and the directors liked it so much they put it in the movie.
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The large delivery truck that almost hits Thomas Crown at the very beginning, as he walks across the street to the museum, is actually the same truck that is carrying his "Trojan horse" to the museum. The driver and license plate are the same (PB9975). In line with the theme and use of the Greek "Trojan Horse" is also the idea of a Greek tragedy; that he (Crown) would be killed by the very truck he hired to carry out his heist; felled by the very events he put into motion. An important part of Greek tragedy is hubris which is shown prominently in Thomas Crown.
Edit Submitted by Luna Negra Time
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The men sent to search TC's apartment in his absence arrive in a truck marked "Aladdin" Cleaning Services but on their shirts the name is misspelled with two Ls and one D - "Alladin". A clue that they are not real cleaning people?
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The car that Crown drives on Martinique was originally intended to be used for Arnold Schwarzenegger's character in Last Action Hero, another John McTiernan film.
Edit Submitted by Ral0618
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The actual glider used in the movie was a "Duo-Discus x" manufactured by Schempp-hirth and was the personal plane of millionaire Richard S. DuPont. The gliders sold new in 1999 (when the movie was made) for about $100,000. The DuPonts, besides being chemical giants, were pioneers in American gliding.
Edit Submitted by Luna Negra Time
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After Thomas has stolen the first painting and is coming out of the museum main gates, you can see a balcony in the background with a man in a bowler hat and suit standing on it. A clue to viewers who notice it maybe?
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Not a mistake, just to notice: Thomas Crown (Pierce Brosnan) uses the name Jimmy more than once. First, he refers to his chauffeur by that name; next as he walks into his office, he calls out to another employee by that name; later in the film, even a security guard is called Jimmy. [Maybe a bit of observation; it used to be not uncommon for Glaswegians to call everyone 'Jimmy'.]
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In the 1968 version of this film Faye Dunaway plays the major role of the insurance lady. In this version, 1999, Faye Dunaway plays the role of the shrink for Mr. Crown.
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