Continuity: When Crown returns home straight after stealing the Monet, the high external shot shows him open the door with his left hand. In the next internal shot he is opening it with his right hand.

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.

Revealing: When Crown enters his office for the first time, he goes up to the window and looks at the river. Just as the camera points out the window, a bright light is seen to shine on Crown's face so that his reflection in the window is clear.

Continuity: When TC opens the briefcase to steal the Monet, the thumb of his latex glove is ripped wide open, which would leave fingerprints. After he places the painting in the briefcase, the next shot shows him closing the brief case and the glove has magically repaired itself.

Continuity: Thomas Crown comes into the police station to identify the thieves. As he is getting ready to leave, Catherine eavesdrops on his conversation as she fixes herself a cup of coffee. She then watches him out the window, drinking her coffee, as he runs to his car. The paper coffee cup changes from a purple swirl design with a little bit of green to a blue and white, geometric border with what appears to be an Asian design.

Continuity: In the first scene in the gallery when TC is admiring the Haystacks painting, he is preparing to eat a bagel or something like that. In the shot looking at him face on, he maneuvers the bagel into position in the bag it is in, so that he can begin to eat it. However, in the next shot - a longer distance profile shot - just after he answers Bobby's question, he is already chewing on a mouthful and starting to tear another piece off.

Continuity: When Catherine Banning is going out to the car for their first date, there is clearly no one in the car. The camera shifts to an inside shot of the back seat, and Crown is suddenly already sitting in it.

Other: Near the start of the movie when Thomas Crown enters his office for the first time, he uses a magnetic swipe card to access the elevator to his office. After he swipes the card, you can hear a 'ding' and the sound of elevator doors opening but you'll notice as he first inserts the card into the reader that the doors are already open.

Plot hole: The beach could be reached only by vehicle, but they only had one car and they arrived separately.