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. See more...
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Plot hole: When Renee Russo was reviewing the tape showing the room with the painting to see who stole the painting, and the tape was blank because the heat generated from the suitcase hidden under the bench, why didn't she just back up the tape completely to see who put the suitcase there in the first place?
Continuity: 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.
Revealing: During the glider scene when they show the close up of Catherine's face with Thomas leaning over her from behind, waving his hands, if you look at her sunglasses you can see all the white screens, the camera crew, the reflection of his hands, etc. You can see this every time they show a close-up of them from the front of the glider.
Revealing: At the beginning, when Thomas Crown is in his car, getting ready to get out and walk up to the museum, they show a close up of his wrist watch to set the time; it says 9:08 a.m. A few minutes later when he is sitting inside the gallery eating his breakfast croissant, if you look carefully at his watch, it shows 4:30. In various other shots, it also shows 5:25 and 6:30, indicating at least 2 hours spent shooting the gallery scene.
Continuity: When the "thieves" are preparing the impressionist wing and inform Thomas Crown that the exhibit is closed, Crown responds with "It's only a quarter to five". Shortly after when the surveillance footage from the time of the robbery is being reviewed, the time stamp on the monitor says 5:54. I doubt that the whole robbery took 1 hour 9 mins, when the time in the movie was around 3 minutes.
Continuity: When they land in Martinique, and are on the airstrip loading up the vehicles, their luggage and the painting go into the second vehicle, a shiny black jeep. However, when they show the aerial shot of them climbing the mountain to Crown's house, the jeep is now painted in camouflage colors.
Plot hole: At the end of the movie when everyone is standing in the gallery looking at the painting now back in place (with the smoke and sprinklers still dripping) they notice that now there is a new painting missing, the one Thomas stole for Catherine. However, none of the other metal wall coverings open or move except for that small side one revealing the empty frame on the wall. This makes no sense why only that one would suddenly open and none of the others.
Revealing: During all shots of the actual glider, you can tell very obviously it is two stunt men in very bad, fake looking wigs. The one up front, "Catherine" now makes her look like a football player. He also has on a long red wig that goes to his shoulders, which is longer than Catherine's hair. In one aerial shot, the stuntman sitting in the rear, which is supposed to be "Thomas", has this dark black bowl cut wig that is parted down the middle and slicked to his head.
Continuity: When TC and Catherine Banning are having breakfast together at TC's house, Jimmy brings Catherine her green shake to drink. In one of the first shots, the glass is only about two-thirds of the way full, however, in the next shot, when she goes to take her first sip of it, the glass is almost filled to the top.