Tomcats

Continuity mistake: When Jill spanks Michael with the special "scarlet letter" paddle, she stands and swings it like a baseball bat. This would've left a sideways A on his butt. Later, you see Michael walking away from the camera, nude. To leave the A at the angle shown in the second scene, Jill would've had to rest on her knees and swing the paddle like an axe.

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Continuity mistake: In the balls scene when Michael is in the Hospital cafeteria and shouts "Doctor, don't eat that," before he yells it the black female doctor in the background is already choking.

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Continuity mistake: The film goes to such lengths to show that Michael has NONE of his possessions left, especially all his clothes, after his stuff is taken by the casino owner's goons. However, whenever Michael goes out in public, he's dressed well again. But later, when he's shown at home, he's once again dressed in rags.

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Continuity mistake: When Michael is with the librarian, and she goes to put on the purple knee high boots, you see her take them out of the chest and put one on, then there's a quick cutaway and both boots are on when she stands.

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Continuity mistake: When Kyle and Natalie are walking on the beach hand-in-hand, and Michael is climbing the cliff to spy on them, watch closely as it shows Michael sliding down the cliff. It's clearly a stunt-double, as the body is short and round, while Jerry O'Connell, who plays Michael, is tall and thin.

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Continuity mistake: When Michael is climbing on the rocks, he turns his head and sees them walking on the beach, and his hair is blowing. The next shot shows his hair lying flat with no wind at all.

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Mistakes

When Carlos (Bill Maher) is explaining to Michael what was a valid roll he says that the redhead rubbed the dice on her chest for good luck and threw them. However she immediately threw the dice when Michael handed them to her. She only rubbed them on her chest and gave them back to Michael on a prior roll.

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Trivia

When Michael collides with a cello player at the charity fundraiser towards the end of the film, the cello player lets out a Wilhelm scream.

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