Plot hole: 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.
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.
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.